Chicago from Atlanta, 23 – 25 Oct: £885 for two, all in
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The verdict
Our verdict
Worth it, if
- $322 per person, $26 below the typical fare on this route
- Hilton Chicago in The Loop: 7.9 from 983 reviews, $530 for two nights
- The Loop puts Millennium Park and the theatres at your doorstep
The catch: The $322 fare has one stop and takes 5h 1m, the Frontier nonstop is $337 per person, and a checked bag is about $240 for two.
Worth it if you want a weekend of architecture, museums and food in jacket weather; skip it if you want warm days or can't stand connections.
Worth it if one stop doesn't bother you. It's $1,174 for two: round-trip Frontier flights at $644 plus 2 nights at Hilton Chicago at $530, with taxes and fees included but no checked bag or spending money. You leave Friday, Oct 23 and come back Sunday, Oct 25, 2026; the 7:20 AM flight has one stop and lands at O'Hare at 11:21 AM after 5h 1m.
The total, before you go
£885 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £485 |
| Hilton Chicago, 2 nights, two guests, taxes in | £399 |
| The total, before you go | £885 |
| Hold luggage each, return (not in the total) | about £181 |
£20 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£243 per person, return
£485 for two, taxes and fees included · Frontier · 1 stop · 5h 1m
Out Fri, Oct 23, 7:20 AM – Fri, Oct 23, 11:21 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £243 | 1 stop | 5h 1m |
| Frontier | £254 | nonstop | 2h 21m |
| Frontier | £268 | 1 stop | 13h 25m |
Prices checked 13 Oct 2026, 22:01 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $322 per person, the fare is $26 below the typical fare on this route. That's 7% under, and it's the lowest we've seen in 30 days across 8 checks. The whole weekend comes to $1,174 for two with Hilton Chicago. A checked bag, resort fees and meals aren't in that total. Late October means jacket weather: forecast highs are 49°F Friday, 57°F Saturday and 53°F Sunday, with rain chances from 23% to 31%, drizzle Saturday and rain Sunday. Chicago handles gray days well, since the Art Institute, deep-dish and the blues clubs are all indoors. The 7:20 AM departure gets you to O'Hare by 11:21 AM, so you still have Friday afternoon. If you'd pay $30 more for two, the Frontier nonstop gets you there in 2h 21m.
The kind of trip this is
This is a city weekend for two: architecture, museums, deep-dish and live blues, at an easy pace with plenty of indoor options if the drizzle shows up. It suits couples or two friends who like to walk between neighborhoods, eat well and finish the night in a club. It's not for anyone hoping for sun or a beach day on the lakefront in late October.
Weather in Chicago, 23 – 25 Oct
Highs 49–57°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 49 °F | 39 °F | 31% |
| Sat 24 Oct | 57 °F | 45 °F | 27% |
| Sun 25 Oct | 53 °F | 49 °F | 23% |
Where to stay in Chicago
We picked Hilton Chicago as the best value: $530 for the 2 nights ($265 a night), room only, rated 7.9 from 983 reviews. It's in The Loop, where the architecture, the theatres and Millennium Park are at your doorstep. Hampton Inn Chicago West Loop Fulton Market Area is the top rated of the three at 8.8 from 776 reviews. It costs $628 for the stay ($314 a night) with breakfast and puts you in the West Loop, close to the restaurant row on Randolph Street. Hampton Inn Chicago McCormick Place in the South Loop is rated 8.5 from 734 reviews and costs $549 for the stay ($275 a night) with breakfast. None of the three offered free cancellation at the rates we found.
Hilton Chicago
£399 for 2 nights, two guests · £200 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£473 for 2 nights, two guests · £237 a night
See roomsHampton Inn Chicago McCormick Place
£414 for 2 nights, two guests · £207 a night
See roomsAll hotels in Chicago for these dates
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Where 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 for the skyline from the water
- See the Bean and the fountains in Millennium Park, steps from The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend a drizzly Saturday at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Friday or Saturday night
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Atlanta | Hartsfield-Jackson Atlanta International (ATL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 5h 1m (1 stop) |
| Distance | 589 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £485 |
| Hotel, 2 nights (Hilton Chicago) | £399 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,277 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: Atlanta to Chicago
| Per person | |
|---|---|
| This trip | £243 per person |
| Lowest in the last 30 days | £243 (14 Oct 2026) |
| Typical price, last 60 days | £262 |
| Price checks | 8 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars.
- Chicago is 1 hour behind Atlanta, so the 11:21 AM arrival is Chicago time.
- The $322 fare flies Atlanta (ATL) to O'Hare (ORD), 589 miles, with one stop and 5h 1m in the air and on the ground.
- A checked bag isn't in the total and runs about $240 for two.
- None of the three hotels offered free cancellation when we checked.
Questions readers ask
Is it worth it?
Worth it if one stop is fine with you. The $322 fare is $26 below the typical fare on this route and the lowest we've seen in 30 days. Hilton Chicago puts you in The Loop. The trade-off is a 5h 1m trip each way and gray, cool weather.
How much is the whole trip for two?
It's $1,174 for two, all in: $644 for the round-trip Frontier flights plus $530 for 2 nights at Hilton Chicago, taxes and fees included. A checked bag (about $240 for two), any resort fees and spending money aren't in it. Prices are what we found when we checked and can change.
Is there a nonstop?
Yes. Frontier has a nonstop at $337 per person, $674 for two, leaving at 8:00 AM and landing at 9:21 AM after 2h 21m. That's $30 more for two than the one-stop fare and saves you a lot of travel time.
What's the weather like?
It's jacket weather. Forecast highs are 49°F Friday, 57°F Saturday and 53°F Sunday, with lows from 39°F to 49°F. Rain chances run from 23% to 31%, with drizzle Saturday and rain Sunday, so plan an indoor day.
Is 2 nights enough?
For a first look, yes. With the 11:21 AM arrival you have Friday afternoon for Millennium Park, then Saturday for the river cruise and the Art Institute, and two nights for deep-dish and blues.
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All trips from Atlanta · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
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- Photo: Mik Dominguez / Pexels, Pexels License
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