Chicago, United States: trips from £170
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Trips to Chicago from every city
Cheapest first, per person, return, taxes and fees included.
Just found · from Fort LauderdaleWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £130 per person below the highest fare we saw for these dates
- Highs 59–68°F, a small chance of rain
- No passport needed
£732 for two · 2 nights · flights, hotel, taxes & fees
Flights £338 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 17h 42m
The catch: Not nonstop: a stop on the way, 17h 42m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Next weekend · from OrlandoLowest in 30 days
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, 3h 11m, landing at O'Hare 7:31 AM Friday
- $270 per person, $25 below the typical fare on this route
- Club Quarters in The Loop scores 8.2 from 5,337 reviews
£1,098 for two · 2 nights · flights, hotel, taxes & fees
Flights £407 + hotel £691, taxes in · a checked bag each adds about £181
Frontier · nonstop · 3h 11m
The catch: Frontier's fare doesn't include a checked bag, which runs about $240 for two, and the 5:20 AM departure means a very early Friday.
Worth it if you pack light and want a city weekend of museums, food and blues; skip it if a 5:20 AM flight is a dealbreaker.
Next weekend · from Las VegasLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier in 3h 47m, $28 per person below typical
- Highs of 52–61°F, 4% rain chance Saturday and 6% Sunday
- Club Quarters in the Loop, rated 8.2 from 5,335 reviews
£1,125 for two · 2 nights · flights, hotel, taxes & fees
Flights £434 + hotel £691, taxes in · a checked bag each adds about £181
Frontier · nonstop · 3h 47m
The catch: It's a red-eye landing at 5:16 AM Saturday, the hotel has no free cancellation, and a checked bag is about $240 for two.
Worth it if the two of you can sleep on a plane and want a walking city weekend; skip it if a 5:16 AM arrival ruins your Saturday.
Just found · from Fort Lauderdale
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, 3h 23m
- Highs 53–62°F, little rain expected
- No passport needed
£817 for two · 2 nights · flights, hotel, taxes & fees
Flights £448 + hotel £369, taxes in · a checked bag each adds about £181
Frontier · nonstop · 3h 23m
The catch: £18 per person above the typical fare on this route.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from NashvilleLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £26 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 58–72°F, a small chance of rain
£859 for two · 2 nights · flights, hotel, taxes & fees
Flights £466 + hotel £393, taxes in · a checked bag each adds about £121
Contour Airlines. Operated by Contour Airlines as Public Charter + Contour Airlines as Public Charter · with a stop · 33h 20m
The catch: Not nonstop: a stop on the way, 33h 20m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from Philadelphia
Chicago
23 – 25 Oct 2026 · 2 nights
- Nonstop on Frontier, 2h 30m
- £14 per person below the typical fare on this route
- Highs 55–71°F, a small chance of rain
£867 for two · 2 nights · flights, hotel, taxes & fees
Flights £473 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 30m
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Next weekend · from AtlantaLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $322 per person, $26 below the typical fare on this route
- Club Quarters in The Loop, rated 8.2 from 5,339 reviews
- Sunday is clear and 65°F for the architecture river cruise
£1,159 for two · 2 nights · flights, hotel, taxes & fees
Flights £485 + hotel £673, taxes in · a checked bag each adds about £181
Frontier · with a stop · 5h 1m
The catch: The $322 fare has one stop and takes 5h 1m, Friday shows a 78% chance of drizzle, and checked bags aren't in the total.
Worth it if you want a walkable city weekend of museums, food and blues; skip it if a stop on a two-night trip feels like too much.
Just found · from AtlantaLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £20 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 49–57°F, a small chance of rain
£885 for two · 2 nights · flights, hotel, taxes & fees
Flights £485 + hotel £399, taxes in · a checked bag each adds about £181
Frontier · with a stop · 5h 1m
The catch: Not nonstop: a stop on the way, 5h 1m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from Dallas-Fort Worth
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, 2h 42m
- £21 per person below the typical fare on this route
- Club Quarters Hotel Central Loop, Chicago, rated 8.2 by 5,339 guests
£1,177 for two · 2 nights · flights, hotel, taxes & fees
Flights £504 + hotel £673, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 42m
The catch: Hold luggage, seat selection and any resort fee are extra: they are not in the total.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from Baltimore
Chicago
23 – 25 Oct 2026 · 2 nights
- Frontier nonstop, BWI to O'Hare in 2h 23m, out 9:58 AM
- $336 per person, $9 below the typical $345 fare
- Forecast highs of 58–75°F with rain chances of 12% to 25%
£1,028 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £507 + hotel £450 + resort fee £72, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 23m
The catch: Frontier's fare doesn't include a checked bag, which runs about $240 for two, and the Aloft rate has no free cancellation.
Worth it if you want a quick city weekend of food, art and blues; skip it if you're after lakefront beach weather.
Just found · from Baltimore
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, 4h 26m
- Cambria Hotel Chicago Loop - Theatre District, rated 8.1 by 1,256 guests
- Free cancellation at Cambria Hotel Chicago Loop - Theatre District
£1,177 for two · 2 nights · flights, hotel, taxes & fees
Flights £512 + hotel £665, taxes in · a checked bag each adds about £181
Frontier · nonstop · 4h 26m
The catch: Hold luggage, seat selection and any resort fee are extra: they are not in the total.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from Dallas-Fort WorthWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- Frontier nonstop at $348 per person, $15 below the typical $363
- Hilton Chicago in The Loop: 7.9 from 981 reviews, $261 a night
- Highs of 59–68°F, good for the river cruise and Millennium Park
£918 for two · 2 nights · flights, hotel, taxes & fees
Flights £525 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · nonstop · 5h 13m
The catch: You land at 12:26 AM Saturday and fly home at 6:20 AM Sunday, and a checked bag is about $240 for two.
Worth it if you want one packed Saturday of architecture, art and deep-dish; skip it if you want a slow weekend or need checked bags.
The weekend after · from TampaLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- Fare $352 per person, $29 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $261 a night
- Highs of 76°F, 72°F and 57°F, rain chance 33% or less
£924 for two · 2 nights · flights, hotel, taxes & fees
Flights £531 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 41m
The catch: The Frontier fare has one stop and the flight up takes 6h 41m, and a checked bag is about $240 for two, not in the total.
Worth it if you pack light and want a Loop weekend of museums and food; skip it if you'd rather pay more to fly nonstop.
Next weekend · from DenverWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Frontier nonstop, 2h 29m, $354 per person round trip
- Fare is $11 under the $365 typical on this route
- Saturday mostly clear at 52°F, Sunday clear at 62°F
£911 for two · 2 nights · flights, hotel, taxes & fees
Flights £534 + hotel £378, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 29m
The catch: The value hotel is by Midway Airport, not downtown, your flight lands at O'Hare at 12:24 AM, and no hotel offered free cancellation.
Worth it if you want a quick city weekend of museums, deep-dish and blues; skip it if landing after midnight would wreck your Saturday.
Next weekend · from Washington, DCLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $354 per person, $12 under the typical $366 on this route
- Saturday mostly clear at 52°F, Sunday clear at 61°F
- Sleep Inn Midway Airport: $369 for 2 nights, breakfast, free cancellation
£899 for two · 2 nights · flights, hotel, taxes & fees
Flights £534 + hotel £366, taxes in · a checked bag each adds about £181
Frontier · with a stop · 7h 24m
The catch: The Frontier flight has one stop and takes 7h 24m, landing at 12:24 AM Saturday; a checked bag is about $240 for two and isn't in the total.
Worth it if you want a low-cost city weekend and don't mind a late arrival; skip it if you need a nonstop or a downtown hotel.
Just found · from DetroitLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- £232 per person below the typical fare on this route
- Lowest in 30 days on this route
- La Quinta Inn & Suites by Wyndham Chicago Downtown, rated 8 by 3,744 guests
£1,174 for two · 2 nights · flights, hotel, taxes & fees
Flights £540 + hotel £635, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 38m
The catch: Not nonstop: a stop on the way, 8h 38m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Next weekend · from AustinLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Fare is $358 per person, $22 below the typical fare
- Saturday mostly clear, Sunday clear at 62°F, 1% rain chance
- Club Quarters scores 8.2 from 5,337 reviews, in The Loop
£1,213 for two · 2 nights · flights, hotel, taxes & fees
Flights £540 + hotel £673, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 23m
The catch: Frontier's fare has one stop and takes 6h 23m, while American's nonstop takes 2h 56m but costs $483 per person.
Worth it if a longer travel day for $358 per person suits you; skip it if you want the 2h 56m nonstop.
Just found · from New OrleansLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- Fare is $21 below the typical fare on this route
- Hilton Chicago in The Loop, rated 7.9 from 983 reviews
- Highs of 58–75°F and rain chances of 12% to 25%
£1,030 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £546 + hotel £418 + resort fee £66, taxes in · a checked bag each adds about £181
Frontier · with a stop · 13h 47m
The catch: The $362 Frontier fare has one stop, takes 13h 47m and lands at 12:24 AM, and a checked bag is about $240 for two.
Worth it if you can give up Friday night to a long connection; skip it if you'd rather pay $1,002 for two on United's 2h 43m nonstop.
Just found · from CharlotteLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £26 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 58–71°F, a small chance of rain
£950 for two · 2 nights · flights, hotel, taxes & fees
Flights £556 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 22h 52m
The catch: Not nonstop: a stop on the way, 22h 52m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Next weekend · from HoustonLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop IAH to O'Hare, leaving 11:36 AM and landing 2:25 PM
- $372 per person, $19 below the typical fare on this route
- Saturday mostly clear at 52°F, Sunday clear at 62°F
£938 for two · 2 nights · flights, hotel, taxes & fees
Flights £561 + hotel £378, taxes in · a checked bag each adds about £181
Frontier · nonstop · 5h 48m
The catch: The $501 hotel is by Midway Airport, not downtown, Friday has a 60% rain chance, and a checked bag and resort fees aren't in the total.
Worth it if you want a low-cost city weekend and don't mind riding in to the sights; skip it if you want to walk out to the Loop.
Just found · from MemphisLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Frontier fare is $374 per person, $286 below the typical fare
- Club Quarters in The Loop scores 8.2 from 5,335 reviews
- Sunday forecast is clear and 65°F, good for the river cruise
£1,162 for two · 2 nights · flights, hotel, taxes & fees
Flights £564 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · with a stop · 14h 51m
The catch: The Frontier fare has one stop and takes 14h 51m overnight, so you land Saturday at 7:51 AM and don't sleep in the room you paid for on Friday.
Worth it if you can sleep through a connection to save $286 per person; skip it if you want all of Friday in Chicago.
Next weekend · from MinneapolisWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $378 per person, $19 below the typical fare on this route
- Hyatt Centric in The Loop: 8.5 from 1,003 reviews, free cancellation
- Sunday is clear and 65°F with a 0% chance of rain
£1,208 for two · 2 nights · flights, hotel, taxes & fees
Flights £570 + hotel £638, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 58m
The catch: The Frontier fare has one stop and takes 8h 58m for 355 miles, landing at 6:31 PM Friday, a day with an 82% chance of drizzle.
Worth it if you'd trade Friday's travel time for the lower fare; skip it if you'd pay $557 per person for American's 1h 44m nonstop.
Just found · from New OrleansWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Cambria Hotel Chicago Loop - Theatre District, rated 8.1 by 1,256 guests
- Free cancellation at Cambria Hotel Chicago Loop - Theatre District
- Highs 52–62°F, little rain expected
£1,236 for two · 2 nights · flights, hotel, taxes & fees
Flights £571 + hotel £665, taxes in · a checked bag each adds about £181
Frontier · with a stop · 14h 2m
The catch: Not nonstop: a stop on the way, 14h 2m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from Raleigh-DurhamLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £25 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 58–72°F, a small chance of rain
£966 for two · 2 nights · flights, hotel, taxes & fees
Flights £573 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 15m
The catch: Not nonstop: a stop on the way, 6h 15m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from CincinnatiLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Round trip at $384 per person, $280 below the typical fare
- All three hotels in The Loop, by Millennium Park
- Sunday forecast clear at 64°F for the architecture river cruise
£1,177 for two · 2 nights · flights, hotel, taxes & fees
Flights £579 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 48m
The catch: Frontier's fare has one stop and takes 6h 48m for 252 miles, Friday shows a 75% chance of rain, and resort fees and a checked bag aren't included.
Worth it if a 6h 48m trip with one stop is a fair trade for the savings; skip it if you want a quick nonstop.
Just found · from Syracuse37% below typicalWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $385 per person, $234 below the typical fare on this route
- Club Quarters in the Loop, rated 8.2 from 5,335 reviews
- Sunday is clear at 65°F with a 1% chance of rain
£1,179 for two · 2 nights · flights, hotel, taxes & fees
Flights £580 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · with a stop · 15h 20m
The catch: Frontier's 1 stop stretches the outbound to 15h 20m, leaving 5:31 PM Friday and landing 7:51 AM Saturday, and Friday shows an 84% rain chance.
Worth it if you can sleep through an overnight connection to save $234 per person; skip it if you need to arrive rested on Saturday.
Just found · from BostonWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Hyatt Place Chicago/Downtown - The Loop, rated 8.2 by 1,959 guests
- Free cancellation at Hyatt Place Chicago/Downtown - The Loop
- Highs 58–65°F, a small chance of rain
£1,226 for two · 2 nights · flights, hotel, taxes & fees
Flights £582 + hotel £644, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 34m
The catch: Not nonstop: a stop on the way, 6h 34m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from ColumbusLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- $386 per person, $220 below the typical fare on this route
- Hampton Inn scores 8.5 from 734 reviews, breakfast included
- Saturday looks clear at 65°F, good for the river cruise
£993 for two · 2 nights · flights, hotel, taxes & fees
Flights £582 + hotel £412, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 57m
The catch: The Frontier fare has one stop and takes 8h 57m to cover 275 miles, landing at 12:24 AM Saturday.
Worth it if a late Friday arrival is fine in exchange for a 36% lower fare; skip it if you want Friday night in the city.
Just found · from ClevelandLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- £167 per person below the typical fare on this route
- Lowest in 30 days on this route
- Hyatt Place Chicago/Downtown - The Loop, rated 8.2 by 1,959 guests
£1,238 for two · 2 nights · flights, hotel, taxes & fees
Flights £594 + hotel £644, taxes in · a checked bag each adds about £181
Frontier · with a stop · 12h 31m
The catch: Not nonstop: a stop on the way, 12h 31m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from HartfordWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Frontier fare is $400 per person, $68 below the typical fare
- Club Quarters in the Loop scores 8.2 from 5,335 reviews
- Sunday looks clear, 65°F with a 1% chance of rain
£1,202 for two · 2 nights · flights, hotel, taxes & fees
Flights £603 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · with a stop · 17h 35m
The catch: The Frontier fare has 1 stop and takes 17h 35m overnight, landing Saturday at 7:51 AM, so you'll barely use your first hotel night.
Worth it if you can sleep through a connection and want a museum-and-deep-dish weekend for less; skip it if Friday night in Chicago matters to you.
Just found · from Oklahoma CityLowest in 30 daysNot worth it this week
Chicago
16 – 18 Oct 2026 · 2 nights
- Frontier fare is $406 per person, $335 below the typical fare
- Holiday Inn & Suites Chicago-Downtown by IHG: 7.6 from 461 reviews, free cancellation
- United nonstop option: 2h 25m, landing at 9:40 AM Friday
£1,377 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £612 + hotel £660 + resort fee £105, taxes in · a checked bag each adds about £181
Frontier · with a stop · 27h 57m
The catch: The $406 Frontier fare has 1 stop and takes 27h 57m, so it lands at 12:24 AM on Oct 18, the day you fly home.
Worth it if you can pay $587 per person for the United nonstop; skip it if the $406 Frontier fare is the only fare that fits your budget.
Next weekend · from BuffaloWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $413 per person, $293 below the highest fare we saw
- Saturday and Sunday clear, with a 2% and 4% rain chance
- Sleep Inn Midway Airport: breakfast and free cancellation, $367 for 2 nights
£988 for two · 2 nights · flights, hotel, taxes & fees
Flights £623 + hotel £366, taxes in · a checked bag each adds about £181
Frontier · with a stop · 5h 47m
The catch: Frontier connects, so the outbound takes 5h 47m against 2h nonstops, and a checked bag is about $240 for two, not in the total.
Worth it if you'd rather save on the fare than on the hours; skip it if you want a nonstop or a downtown bed.
Just found · from PittsburghLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $418 per person, $241 below the typical fare on this route
- La Quinta in The Loop: 8 from 3,744 reviews, breakfast included
- Free cancellation at La Quinta, and Sunday's forecast is clear at 65°F
£1,242 for two · 2 nights · flights, hotel, taxes & fees
Flights £630 + hotel £612, taxes in · a checked bag each adds about £181
Frontier · with a stop · 13h
The catch: The Frontier fare has one stop and takes 13 hours overnight, landing at 7:51 AM Saturday, so you'll spend Friday's hotel night in transit.
Worth it if you'll trade a night of sleep for the lower fare; skip it if you want a nonstop and a full Friday evening in Chicago.
Next weekend · from PhoenixWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Fare at $420 per person, $7 under the $427 typical
- Clear skies forecast Saturday and Sunday, highs of 53°F and 62°F
- Club Quarters in The Loop, rated 8.2 from 5,337 reviews
£1,324 for two · 2 nights · flights, hotel, taxes & fees
Flights £633 + hotel £691, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 13m
The catch: The $420 fare has one stop, takes 6h 13m and lands at 12:31 AM Saturday, and a checked bag is about $240 for two.
Worth it if you want a walkable city weekend of architecture, art and deep-dish; skip it if landing after midnight wrecks your Friday.
Just found · from HartfordWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £20 per person below the typical fare on this route
- Highs 55–71°F, a small chance of rain
- No passport needed
£1,036 for two · 2 nights · flights, hotel, taxes & fees
Flights £642 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 35h 58m
The catch: Not nonstop: a stop on the way, 35h 58m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from San AntonioLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- £22 per person below the typical fare on this route
- Lowest in 30 days on this route
- La Quinta Inn & Suites by Wyndham Chicago Downtown, rated 8 by 3,744 guests
£1,283 for two · 2 nights · flights, hotel, taxes & fees
Flights £648 + hotel £635, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 59m
The catch: Not nonstop: a stop on the way, 8h 59m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from BoiseWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- $430 per person, $68 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $522
- Saturday high of 60°F with a 16% rain chance
£1,042 for two · 2 nights · flights, hotel, taxes & fees
Flights £648 + hotel £393, taxes in · a checked bag each adds about £106
Alaska. Operated by SkyWest Airlines as Alaska SkyWest · with a stop · 8h 55m
The catch: The fare we priced has one stop and takes 8h 55m to get there, while the American nonstop takes 3h 47m but costs $539 per person.
Worth it if saving $68 per person is worth a long Friday of travel to you; skip it if two nights already feels too short.
Next weekend · from Salt Lake CityLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Frontier fare is $470 per person, $28 below the typical fare
- Saturday and Sunday look clear, with highs of 53°F and 62°F
- Canopy By Hilton Chicago Central Loop scores 8.9 from 308 reviews
£1,078 for two · 2 nights · flights, hotel, taxes & fees
Flights £709 + hotel £369, taxes in · a checked bag each adds about £181
Frontier · with a stop · 7h 8m
The catch: The Frontier flight has 1 stop, takes 7h 8m and lands at 12:24 AM, and a checked bag is about $240 for two, not in the total.
Worth it if you can handle a late Friday arrival for a clear-weather city weekend; skip it if you need a nonstop or a central hotel.
Just found · from Salt Lake CityWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £150 per person below the highest fare we saw for these dates
- Highs 59–68°F, a small chance of rain
- No passport needed
£1,102 for two · 2 nights · flights, hotel, taxes & fees
Flights £709 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 7h 8m
The catch: Not nonstop: a stop on the way, 7h 8m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from JacksonvilleWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $522 for two nights
- Fare of $471 per person, $8 below the $479 median
- Highs of 55–71°F, with rain chances of 29% or less
£1,104 for two · 2 nights · flights, hotel, taxes & fees
Flights £710 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 12h 7m
The catch: The Frontier fare has one stop and takes 12h 7m to get there, and a checked bag is about $240 for two on top.
Worth it if you'll trade a long Friday of travel for the lower fare; skip it if layovers on a 2-night trip wear you out.
Next weekend · from Little Rock18% below typical
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on American, 2h 7m, leaving Little Rock 7:53 PM Friday
- $484 per person, $108 below the typical fare on this route
- Cambria in The Loop: 8.1 from 1,256 reviews, free cancellation
£1,394 for two · 2 nights · flights, hotel, taxes & fees
Flights £730 + hotel £665, taxes in · a checked bag each adds about £121
American. Operated by Republic Airways as American Eagle · nonstop · 2h 7m
The catch: A checked bag is about $160 for two and isn't in the total, and Friday has a 60% rain chance around your 10:00 PM arrival.
Worth it if you want a walkable city weekend of museums, deep-dish and blues; skip it if you want warm weather or a full Friday there.
Just found · from OmahaLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £173 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 60–76°F, a small chance of rain
£1,129 for two · 2 nights · flights, hotel, taxes & fees
Flights £736 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 27h 25m
The catch: Not nonstop: a stop on the way, 27h 25m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from West Palm BeachLowest in 30 days
Chicago
23 – 25 Oct 2026 · 2 nights
- 3h 27m American nonstop, leaving 12:33 PM Friday, Oct 23
- $489 per person, $82 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 981 reviews
£1,131 for two · 2 nights · flights, hotel, taxes & fees
Flights £737 + hotel £393, taxes in · a checked bag each adds about £121
American · nonstop · 3h 27m
The catch: A checked bag is about $160 for two and isn't in the total, and Hilton Chicago doesn't offer free cancellation.
Worth it if you want museums, deep-dish and live music over two days; skip it if you need a beach or a slow pace.
Next weekend · from Fort MyersLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $494 per person, $98 below the typical fare on this route
- Saturday and Sunday forecast: 1% rain chance, highs 52°F and 62°F
- River Hotel in The Loop scores 8.3 from 7,928 reviews
£1,122 for two · 2 nights · flights, hotel, taxes & fees
Flights £745 + hotel £378, taxes in · a checked bag each adds about £181
Frontier · with a stop · 10h 54m
The catch: The Frontier fare has 1 stop and takes 10h 54m, landing at 10:39 PM, while the American nonstop costs $545 per person.
Worth it if a long Friday travel day is fine for $98 per person saved; skip it if Friday evening in the city matters to you.
Just found · from St. LouisLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- £151 per person below the typical fare on this route
- Lowest in 30 days on this route
- Club Quarters Hotel Central Loop, Chicago, rated 8.2 by 5,339 guests
£1,427 for two · 2 nights · flights, hotel, taxes & fees
Flights £754 + hotel £673, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 38m
The catch: Not nonstop: a stop on the way, 6h 38m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from Richmond33% below typical
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on American, 2h 23m
- £189 per person below the typical fare on this route
- La Quinta Inn & Suites by Wyndham Chicago Downtown, rated 8 by 3,744 guests
£1,436 for two · 2 nights · flights, hotel, taxes & fees
Flights £754 + hotel £682, taxes in · a checked bag each adds about £121
American · nonstop · 2h 23m
The catch: Hold luggage, seat selection and any resort fee are extra: they are not in the total.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from Des Moines26% below typicalNot worth it this week
Chicago
16 – 18 Oct 2026 · 2 nights
- $504 per person, $185 below the typical fare on this route
- United and American nonstops at $587 per person, 96 to 101 minutes
- Club Quarters in The Loop, rated 8.2 from 5,335 reviews
£1,453 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £760 + hotel £598 + resort fee £95, taxes in · a checked bag each adds about £181
Frontier · with a stop · 27h 59m
The catch: The $504 Frontier fare has one stop and takes 27h 59m, landing at 12:24 AM on Sunday, Oct 18, the day the trip ends.
Worth it if you switch to a $587 nonstop and want a walkable Loop weekend; skip the Frontier fare entirely.
Just found · from Norfolk17% below typicalWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £81 per person below the typical fare on this route
- Highs 51–58°F, a small chance of rain
- No passport needed
£1,175 for two · 2 nights · flights, hotel, taxes & fees
Flights £776 + hotel £399, taxes in · a checked bag each adds about £181
Frontier · with a stop · 35h 58m
The catch: Not nonstop: a stop on the way, 35h 58m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from SpokaneLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- Fare is $520 per person, $82 below typical, 14% less
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $522
- Highs of 76°F and 72°F for Friday and Saturday
£1,177 for two · 2 nights · flights, hotel, taxes & fees
Flights £784 + hotel £393, taxes in · a checked bag each adds about £106
Alaska · with a stop · 7h 54m
The catch: The Alaska flight stops once and takes 7h 54m overnight, landing at 5:40 AM Saturday, and a checked bag is about $140 for two.
Worth it if you can sleep on a red-eye and want a big-city weekend; skip it if you need a full night in bed before sightseeing.
Just found · from ProvidenceLowest in 30 daysWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- $148 below the typical fare on this route, lowest in 30 days
- Hilton Chicago in the Loop, rated 7.9 from 983 reviews
- Saturday high of 75°F, rain chances 16% to 23%
£1,214 for two · 2 nights · flights, hotel, taxes & fees
Flights £796 + hotel £418, taxes in · a checked bag each adds about £136
JetBlue · with a stop · 5h 44m
The catch: The $528 JetBlue fare has one stop and takes 5h 44m from a 6:40 AM start; resort fees and a checked bag are not in the total.
Worth it if an early start and one stop are fine for a city weekend; skip it if you'd rather pay more for the 2h 44m United nonstop.
Next weekend · from NorfolkWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on United, 2h 33m, leaving at 6:20 AM Friday
- $530 per person, $86 below the typical fare on this route
- Club Quarters in The Loop, rated 8.2 from 5,335 reviews
£1,492 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £799 + hotel £598 + resort fee £95, taxes in · a checked bag each adds about £121
United. Operated by Republic Airways DBA United Express · nonstop · 2h 33m
The catch: Friday has a 78% chance of drizzle, none of the three hotels offers free cancellation, and a checked bag is about $160 for two, which isn't in the total.
Worth it if you want a walkable city weekend of museums, food and blues; skip it if you need a refundable room or can't stand drizzle.
Just found · from AlbanyLowest in 30 days
Chicago
23 – 25 Oct 2026 · 2 nights
- Nonstop on United, 2h 33m
- £118 per person below the typical fare on this route
- Lowest in 30 days on this route
£1,227 for two · 2 nights · flights, hotel, taxes & fees
Flights £810 + hotel £418, taxes in · a checked bag each adds about £121
United · nonstop · 2h 33m
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from TucsonLowest in 30 days
Chicago
23 – 25 Oct 2026 · 2 nights
- Nonstop on American, 3h 44m
- £170 per person below the typical fare on this route
- Lowest in 30 days on this route
£1,217 for two · 2 nights · flights, hotel, taxes & fees
Flights £823 + hotel £393, taxes in · a checked bag each adds about £121
American · nonstop · 3h 44m
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Next weekend · from Charleston
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on American, 2h 43m, landing at 8:59 AM Friday
- $547 per person, $22 below the $569 typical fare
- Clear Saturday and Sunday, highs 52°F and 62°F, 1% rain
£1,498 for two · 2 nights · flights, hotel, taxes & fees
Flights £825 + hotel £673, taxes in · a checked bag each adds about £121
American · nonstop · 2h 43m
The catch: Friday has a 60% chance of rain, the value hotel has no free cancellation, and resort fees and a checked bag aren't in the total.
Worth it if you want a quick city weekend of architecture, art and deep-dish; skip it if you need a refundable room at the value hotel.
Just found · from SavannahLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- £103 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 53–62°F, little rain expected
£1,203 for two · 2 nights · flights, hotel, taxes & fees
Flights £834 + hotel £369, taxes in · a checked bag each adds about £121
American. Operated by PSA Airlines as American Eagle · with a stop · 5h 15m
The catch: Not nonstop: a stop on the way, 5h 15m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Next weekend · from AlbuquerqueLowest in 30 days
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on American, 3h 2m, landing at 5:59 PM Friday
- $599 per person, $109 below the typical fare on this route
- Club Quarters Hotel Central Loop, Chicago: 8.2 from 5,337 reviews
£1,576 for two · 2 nights · flights, hotel, taxes & fees
Flights £903 + hotel £673, taxes in · a checked bag each adds about £121
American · nonstop · 3h 2m
The catch: Friday has a 60% chance of rain, the $893 hotel has no free cancellation, and resort fees and a checked bag aren't in the total.
Worth it if you want a walkable city weekend of museums, deep-dish and blues; skip it if you're hoping for warm weather.
Just found · from LouisvilleLowest in 30 days
Chicago
23 – 25 Oct 2026 · 2 nights
- Nonstop on United. Operated by Republic Airways DBA United Express, 1h 41m
- £106 per person below the typical fare on this route
- Lowest in 30 days on this route
£1,309 for two · 2 nights · flights, hotel, taxes & fees
Flights £909 + hotel £400, taxes in · a checked bag each adds about £121
United. Operated by Republic Airways DBA United Express · nonstop · 1h 41m
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from BirminghamWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Club Quarters Hotel Central Loop, Chicago, rated 8.2 by 5,336 guests
- Highs 56–63°F, little rain expected
- No passport needed
£1,582 for two · 2 nights · flights, hotel, taxes & fees
Flights £909 + hotel £673, taxes in · a checked bag each adds about £121
MX + F9 · with a stop · 38h 26m
The catch: Not nonstop: 2 stops on the way, 38h 26m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from IndianapolisLowest in 30 days
Chicago
23 – 25 Oct 2026 · 2 nights
- Nonstop on American. Operated by Republic Airways as American Eagle, 1h 25m
- £35 per person below the typical fare on this route
- Lowest in 30 days on this route
£1,354 for two · 2 nights · flights, hotel, taxes & fees
Flights £960 + hotel £393, taxes in · a checked bag each adds about £121
American. Operated by Republic Airways as American Eagle · nonstop · 1h 25m
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from IndianapolisLowest in 30 days
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on United, 2h 39m
- Lowest in 30 days on this route
- Cambria Hotel Chicago Loop - Theatre District, rated 8.1 by 1,256 guests
£1,693 for two · 2 nights · flights, hotel, taxes & fees
Flights £1,028 + hotel £665, taxes in · a checked bag each adds about £121
United · nonstop · 2h 39m
The catch: Hold luggage, seat selection and any resort fee are extra: they are not in the total.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Lowest fares to Chicago by city, last 30 days
| From | Lowest, 30 days | Checks |
|---|---|---|
| Fort Lauderdale | £168 | 12 |
| Orlando | £204 | 6 |
| Philadelphia | £214 | 10 |
| Las Vegas | £217 | 6 |
| Boston | £225 | 9 |
| Nashville | £233 | 8 |
| Baltimore | £242 | 14 |
| Atlanta | £243 | 14 |
| New York | £243 | 23 |
| Dallas-Fort Worth | £251 | 21 |
| Denver | £253 | 8 |
| Miami | £264 | 6 |
| Tampa | £265 | 6 |
| Washington, DC | £267 | 20 |
| Austin | £270 | 6 |
| Detroit | £270 | 6 |
| New Orleans | £273 | 14 |
| Syracuse | £273 | 10 |
| Minneapolis | £274 | 9 |
| Charlotte | £278 | 10 |
When to go
| Month | Season |
|---|---|
| January | avoid |
| February | avoid |
| March | avoid |
| April | fine |
| May | best |
| June | best |
| July | best |
| August | best |
| September | best |
| October | best |
| November | fine |
| December | avoid |
- June, July, August: Lakefront beaches, street festivals and Lollapalooza in early August
- November, December: Christkindlmarket and holiday lights on Michigan Avenue
December, January, February, March: Bitter cold and wind off the lake
Where to stay in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
- Hear live blues at Kingston Mines
Good to know
| Airports | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Passport from United States | No passport needed |
| Price level | upscale |
| Time zone | America/Chicago |
| Kind of trip | city, culture, food, nightlife, shopping |
Chicago in pictures
Questions about Chicago
When is the best time to visit Chicago?
May, June, July, August, September and October. December, January, February, March: Bitter cold and wind off the lake
Do I need a passport for Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
What is the cheapest flight to Chicago right now?
Chicago from Fort Lauderdale, 23 – 25 Oct 2026, from £170 per person return, is the cheapest trip we have published; the full list is on this page.
How expensive is Chicago on the ground?
Chicago is upscale by US standards: plan about £98 per person per day for food, getting around and tickets.
Prices converted from US dollars at the rate of 15 Oct 2026.