Chicago from St. Louis, Oct 23–25: $1,884 for two, all in
The verdict
Our verdict
Not worth it this week
- $596 per person, $90 below the typical fare on this route
- Overcast highs of 69–74°F with rain chances of 17% or less
- Aloft by Marriott Chicago Mag Mile scores 8.1 from 2,535 reviews
The catch: The $596 fare has 3 stops and 31h 34m of travel, and the flight home doesn't land until 1:31 PM on Monday, Oct 26.
Worth it if you can take Monday off and don't mind long layovers; skip it if you want a full weekend in the city.
Not worth it this week. The trip costs $1,884 for two: $1,192 in flights, plus $597 for 2 nights at Aloft by Marriott Chicago Mag Mile and its $95 resort fee, with taxes and fees included but not bags or spending money. It runs Friday, Oct 23 to Sunday, Oct 25, 2026, on Frontier (F9) with 3 stops, so it's not a nonstop.
The total, before you go
$1,884 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $1,192 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | $597 |
| Resort fee, collected at the desk | $95 |
| The total, before you go | $1,884 |
| A checked bag each, round trip (not in the total) | about $240 |
$90 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); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$596 per person, round trip
$1,192 for two, taxes and fees included · Frontier · 3 stops · 31h 34m
Out Fri, Oct 23, 5:53 PM – Sat, Oct 24, 12:26 AM · back Sun, Oct 25, 12:30 PM – Mon, Oct 26, 1:31 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $596 | 3 stops | 31h 34m |
| United | $686 | nonstop | 3h 9m |
| Frontier | $632 | 2 stops | 28h 33m |
Prices checked Oct 15, 2026, 1:32 PM CDT. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
The fare is $596 per person, 13% under the $686 median of our earlier checks on this route. The forecast for Oct 23–25 is overcast, with highs of 69–74°F and rain chances from 9% to 17%. That's good walking weather for the river and the lakefront. The problem is the routing. It has 3 stops, you get in at 12:26 AM on Saturday, and Sunday's flight home lands at 1:31 PM on Monday. We also found a United nonstop that leaves at 8:00 AM and lands at 9:31 AM. It's $686 per person ($1,372 for two in fares), which is the typical price. In the past 30 days, fares on this route have been as low as $500 per person. For a 263-mile, two-night getaway, we'd wait for a better schedule.
The kind of trip this is
This is a city weekend of skyscraper architecture, museums, deep-dish pizza and live blues. Days are for a river cruise and Millennium Park, and nights are for a blues club or a ballgame. It suits a couple or two friends who like to wander neighborhoods and eat well. With only 2 nights and a late Friday arrival, the trip is short and packed, not slow.
Weather in Chicago, Oct 23–25
Highs 69–74°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 72 °F | 59 °F | 9% |
| Sat, Oct 24 | 74 °F | 61 °F | 11% |
| Sun, Oct 25 | 69 °F | 59 °F | 17% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile is the best value and the hotel in our total. It's $597 for 2 nights ($299 a night) and scores 8.1 from 2,535 reviews. It's in Streeterville, and its $95 resort fee is already counted in the total. Sable At Navy Pier Chicago, Curio Collection By Hilton is the top-rated pick at 8.9 from 888 reviews. It costs $803 for the stay plus $128 in fees at the property, on the Near North Side. Hilton Chicago is listed as the budget pick at $608 ($304 a night), with 7.9 from 982 reviews and $97 in fees at the property. It's in The Loop, which puts architecture, theaters and Millennium Park at your door. Magnificent Mile / Streeterville is the area for shopping on Michigan Avenue. None of the three offers free cancellation.
Aloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 a night
See roomsSable At Navy Pier Chicago, Curio Collection By Hilton
$803 for 2 nights, two guests · $402 a night
See roomsHilton Chicago
$608 for 2 nights, two guests · $304 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
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend a morning at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field
Also worth it
- Visit the Art Institute of Chicago
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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 | 31h 34m (3 stops) |
| Distance | 263 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,192 |
| Hotel, 2 nights (Aloft by Marriott Chicago Mag Mile) | $597 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,309 |
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 | $596 per person |
| Lowest in the last 30 days | $500 (Oct 14, 2026) |
| Typical price, last 60 days | $686 |
| Price checks | 9 |
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).
- No passport needed, the currency is the US dollar and there's no time difference from St. Louis
- The $596 fare on Frontier (F9) has 3 stops and 31h 34m of total travel time
- A checked bag is about $240 for two and isn't in the $1,884 total
- All three hotels are room only, and none offers free cancellation
- Chicago has two airports, O'Hare (ORD) and Midway (MDW); this fare flies into O'Hare
Questions readers ask
Is it worth it?
Not this week. The fare is $90 per person under the typical fare, but it has 3 stops and 31h 34m of travel for a 263-mile trip. You'd also land back home on Monday afternoon.
How much is the whole trip for two?
It's $1,884 for two: $1,192 in flights plus $597 for 2 nights at Aloft by Marriott Chicago Mag Mile, and its $95 resort fee. Taxes and fees are included. Checked bags, at about $240 for two, and spending money are not.
Is there a nonstop?
Yes. We found a United nonstop that leaves Friday at 8:00 AM and lands at 9:31 AM. It's $686 per person, or $1,372 for two in fares. That's the typical fare on this route.
What is the weather like?
The forecast is overcast all three days. Highs run 72°F on Friday, 74°F on Saturday and 69°F on Sunday, with lows of 59–61°F. Rain chances are 9% to 17%.
Is 2 nights enough?
For Chicago it can be, with a river cruise, Millennium Park, the Art Institute and a blues club. On this fare, though, you arrive at 12:26 AM Saturday and leave at 12:30 PM Sunday. That leaves about one full day.
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Worth it if you want sun, sand and a pool; skip it if you want a city to walk.
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Nov 14–21, 2026 · 7 nights
- $313 per person below the highest fare we saw for these dates
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$2,818 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,284 + hotel $1,325 + resort fee $209, taxes in · a checked bag each adds about $160
American · with a stop · 11h 43m
The catch: The flight has one stop and takes 11h 43m, and a checked bag is about $160 for two, which is not in the total.
Worth it if a long one-stop flight is fine for a week of warm beach days; skip it if you need a nonstop or free cancellation.
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