Chicago from St. Louis, Oct 16–18: $1,893 for two, all in
The verdict
Our verdict
Worth it, if
- $200 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.
Round-trip flights on Frontier from St. Louis to Chicago cost $500 per person for Oct 16–18, 2026 when we checked, $200 below the typical fare on this route. Three places to stay start at $447 a night for the 2-night stay. Prices move; every link below shows the live price.
The total, before you go
$1,893 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $1,000 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | $893 |
| The total, before you go | $1,893 |
| A checked bag each, round trip (not in the total) | about $240 |
$200 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); 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
$500 per person, round trip
$1,000 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 | $500 | 1 stop | 6h 38m |
| United. Operated by Gojet Airlines DBA United Express | $579 | nonstop | 1h 32m |
| American | $579 | nonstop | 1h 28m |
Prices checked Oct 14, 2026, 8:48 AM CDT. 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, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 59 °F | 49 °F | 82% |
| Sat, Oct 17 | 58 °F | 46 °F | 12% |
| Sun, Oct 18 | 65 °F | 50 °F | 0% |
Where to stay in Chicago
Club Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 a night
See roomsMoxy Chicago Downtown
$904 for 2 nights, two guests · $452 a night
See roomsCentral Loop Hotel
$893 for 2 nights, two guests · $447 a night
See roomsAll hotels in Chicago for these dates
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
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
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
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 | $1,000 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $893 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,413 |
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 | $500 per person |
| Lowest in the last 30 days | $500 (Oct 14, 2026) |
| Typical price, last 60 days | $700 |
| Price checks | 7 |
Good to know
- Passport: no passport needed for travelers 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 $2,413 for two: $1,000 in flights, $893 for the hotel and $520 for food, getting around and tickets.
What is the weather like in Chicago Oct 16–18?
Highs 58–65°F, a small chance of rain
Do I need a passport for Chicago?
No. No passport needed for travelers 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 $500 a good price for St. Louis to Chicago?
It is 29% below the typical $700 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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