Chicago from Memphis, 16 – 18 Oct: £1,162 for two, all in
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The verdict
Our verdict
Worth it, if
- 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
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.
Worth it if you can handle an overnight connection: $1,542 for two, with the Frontier flights at $748 plus 2 nights at Club Quarters Hotel Central Loop, Chicago at $794, taxes and fees included. The trip is Oct 16–18, 2026. You leave Memphis Friday at 5:00 PM, make one stop and land at O'Hare Saturday at 7:51 AM, 14h 51m later; resort fees, a checked bag and spending money are not in the total.
The total, before you go
£1,162 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £564 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £598 |
| The total, before you go | £1,162 |
| Hold luggage each, return (not in the total) | about £181 |
£216 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
£282 per person, return
£564 for two, taxes and fees included · Frontier · 1 stop · 14h 51m
Out Fri, Oct 16, 5:00 PM – Sat, Oct 17, 7:51 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £282 | 1 stop | 14h 51m |
| United | £417 | nonstop | 2h 6m |
| MX + F9 | £412 | 2 stops | 34h 40m |
Prices checked 14 Oct 2026, 10:42 GMT-5. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $374 per person, the Frontier fare is $286 below the typical fare on this route, a 43% gap, and it's the lowest we've seen in 30 days. We checked 12 offers, and fares ran from $374 to $589 per person. That brings the whole weekend to $1,542 for two with the hotel in The Loop, taxes and fees included. Mid-October in Chicago means cool weather for walking the city. The forecast shows rain Friday (84% chance, 57°F), clouds Saturday at 58°F and a clear Sunday at 65°F, which is your day for the lakefront and Millennium Park. Since this fare lands Saturday morning, you'd miss Friday's rain anyway. If the overnight routing is a dealbreaker, United flies nonstop in 2h 6m for $553 per person. These prices are what we found when we checked, and they can change.
The kind of trip this is
This is a two-night city weekend built around food, architecture and live music. It suits a couple or two friends who like to walk, eat well and stay out a little late, as long as they don't mind arriving tired Saturday morning. The pace is compact: a full Saturday, a clear Sunday, then home. Plan on deep-dish, a museum, a river cruise and a blues club, with The Loop as your base.
Weather in Chicago, 16 – 18 Oct
Highs 57–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 57 °F | 49 °F | 84% |
| Sat 17 Oct | 58 °F | 46 °F | 18% |
| Sun 18 Oct | 65 °F | 50 °F | 1% |
Where to stay in Chicago
Club Quarters Hotel Central Loop, Chicago is our best-value pick and the hotel in the total. It's $794 for the stay ($397 a night) for a Club Room in The Loop and scores 8.2 from 5,335 reviews. Central Loop Hotel is the budget pick at the same $794 for the stay. It scores 8.1 from 3,685 reviews and gives you a Double Room, also in The Loop. Omni Chicago Hotel is the top rated at 8.9 from 677 reviews. It costs $1,277 for the stay ($639 a night) for a One Bedroom Suite with 1 king bed in River North, home to galleries, steakhouses and the city's nightlife core. From The Loop, architecture, theatres and Millennium Park are right outside your door. All three are room only, and none offers free cancellation.
Club Quarters Hotel Central Loop, Chicago
£598 for 2 nights, two guests · £299 a night
See roomsOmni Chicago Hotel
£963 for 2 nights, two guests · £482 a night
See roomsCentral Loop Hotel
£598 for 2 nights, two guests · £299 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 on Sunday, when the forecast is clear and 65°F
- See the Bean and the fountains in Millennium Park, in The Loop near both budget hotels
- Visit the Art Institute of Chicago on overcast Saturday for an easy indoor plan
- Eat deep-dish at Lou Malnati's or Pequod's on Saturday night
- Hear live blues at Kingston Mines to close out the weekend
Also worth it
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Memphis | Memphis International (Frederick W. Smith) (MEM) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 14h 51m (1 stop) |
| Distance | 483 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £564 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £598 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,554 |
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: Memphis to Chicago
| Per person | |
|---|---|
| This trip | £282 per person |
| Lowest in the last 30 days | £282 (14 Oct 2026) |
| Typical price, last 60 days | £497 |
| 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: it's a domestic trip paid in US dollars, with no time difference from Memphis.
- The Frontier fare leaves MEM Friday at 5:00 PM, makes one stop and reaches O'Hare (ORD) Saturday at 7:51 AM.
- None of the three hotels offers free cancellation, and all are room only.
- The $1,542 total covers the flights and the hotel with taxes and fees; resort fees, a checked bag and spending money are extra.
- Chicago also has Midway (MDW), but this fare lands at O'Hare.
Questions readers ask
Is it worth it?
Worth it if the overnight connection doesn't bother you. The fare is $374 per person, $286 below the typical fare on this route, but the trip takes 14h 51m with one stop. If you want Friday in Chicago, United flies nonstop in 2h 6m for $553 per person.
How much is the whole trip for two?
It's $1,542 for two: $748 for the Frontier flights and $794 for 2 nights at Club Quarters Hotel Central Loop, Chicago, taxes and fees included. Resort fees, a checked bag and spending money are not part of that number.
Do I need a passport?
No. Memphis to Chicago is a domestic flight, you pay in US dollars, and both cities are in the same time zone.
What is the weather like?
Friday, Oct 16 shows an 84% chance of rain and a high of 57°F. Saturday is overcast at 58°F with an 18% chance. Sunday is clear at 65°F with a 1% chance.
Is 2 nights enough?
With this fare you get Saturday and Sunday in the city, since you land at 7:51 AM Saturday. That's enough time for a river cruise, the Art Institute, Millennium Park, deep-dish and a blues night, but you pay for a Friday hotel night you won't use.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
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