Chicago from St. Louis, 16 – 18 Oct: £1,427 for two, all in
The verdict
Our verdict
Worth it, if
- £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
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.
Chicago is 2 nights from St. Louis, 16 – 18 Oct 2026. The cheapest round trip we found is £377 per person (Frontier, 1 stop, 6h 38m), 29% below the typical £528 on this route. Hotels start at £337 a night; Highs 58–65°F, a small chance of rain.
The total, before you go
£1,427 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £754 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £673 |
| The total, before you go | £1,427 |
| Hold luggage each, return (not in the total) | about £181 |
£151 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
£377 per person, return
£754 for two, taxes and fees included · Frontier · 1 stop · 6h 38m
Out Fri, Oct 16, 5:53 PM – Sat, Oct 17, 12:31 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £377 | 1 stop | 6h 38m |
| United. Operated by Gojet Airlines DBA United Express | £436 | nonstop | 1h 32m |
| American | £436 | nonstop | 1h 28m |
Prices checked 14 Oct 2026, 08:48 GMT-5. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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Why Chicago
Why we picked it: Chicago is the best value we priced for the weekend: $500 round trip, 29% under the typical price.
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Weather in Chicago, 16 – 18 Oct
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 59 °F | 49 °F | 82% |
| Sat 17 Oct | 58 °F | 46 °F | 12% |
| Sun 18 Oct | 65 °F | 50 °F | 0% |
Where to stay in Chicago
Club Quarters Hotel Central Loop, Chicago
£673 for 2 nights, two guests · £337 a night
See roomsMoxy Chicago Downtown
£681 for 2 nights, two guests · £341 a night
See roomsCentral Loop Hotel
£673 for 2 nights, two guests · £337 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
Signature experiences
- 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
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Getting there and around
| Airports in St. Louis | St. Louis Lambert International (STL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 6h 38m (1 stop) |
| Distance | 263 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £754 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £673 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,819 |
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: St. Louis to Chicago
| Per person | |
|---|---|
| This trip | £377 per person |
| Lowest in the last 30 days | £377 (14 Oct 2026) |
| Typical price, last 60 days | £528 |
| Price checks | 7 |
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).
Questions readers ask
How much does 2 nights in Chicago from St. Louis cost?
About £1,819 for two: £754 in flights, £673 for the hotel and £392 for food, getting around and tickets.
What is the weather like in Chicago 16 – 18 Oct?
Highs 58–65°F, a small chance of rain
Do I need a passport for Chicago?
No. No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
How long is the flight from St. Louis to Chicago?
6h 38m with 1 stop on Frontier, on the fare we found.
Is £377 a good price for St. Louis to Chicago?
It is 29% below the typical £528 per person we see on this route, which is why it made the list.
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All trips from St. Louis · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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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
- Photo: K / Pexels, Pexels License