Chicago from St. Louis, Oct 30–Nov 1: $1,434 for two, all in
The verdict
Our verdict
Worth it, if
- Frontier fare $440 per person, $188 below the typical fare
- Hilton Chicago in The Loop, 7.9 from 982 reviews
- Architecture river cruise and the Art Institute, highs 51–56°F
The catch: Frontier's fare has one stop and takes 6h 54m outbound, while American's 88-minute nonstop is $509 per person, and a checked bag is about $240 for two.
Worth it if a lower fare matters more to you than a fast Friday; skip it if a long travel day for a short hop would wear you out.
Worth it if you don't mind a stop: $1,434 for two, all in. That's the Frontier flights at $880 plus 2 nights at Hilton Chicago at $478 and its $76 property fee, with taxes and fees included. You fly Friday, Oct 30 and return Sunday, Nov 1, and the flight isn't nonstop: it has one stop and takes 6h 54m for a 263-mile trip, with checked bags and spending money not in the total.
The total, before you go
$1,434 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $880 |
| Hilton Chicago, 2 nights, two guests, taxes in | $478 |
| Resort fee, collected at the desk | $76 |
| The total, before you go | $1,434 |
| A checked bag each, round trip (not in the total) | about $240 |
$188 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
$440 per person, round trip
$880 for two, taxes and fees included · Frontier · 1 stop · 6h 54m
Out Fri, Oct 30, 12:14 PM – Fri, Oct 30, 7:08 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $440 | 1 stop | 6h 54m |
| American | $509 | nonstop | 1h 28m |
| Frontier | $466 | 3 stops | 32h 10m |
Prices checked Oct 15, 2026, 7:15 PM CDT. Prices change; the binding price is the one on the booking site.
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Why now
The Frontier fare is $440 per person, $188 below the typical fare on this route. That's 30% under the $628 typical fare, and it's the lowest we've seen in 30 days, based on 14 checks. Late October in Chicago tends to be overcast, with typical highs of 51–56°F, lows near 41°F and drizzle in the forecast for Sunday, Nov 1. That makes this a weekend for museums and long dinners more than the lakefront. Pack a jacket, and save the Art Institute and a deep-dish dinner for the wet day. There's no time change from St. Louis and no passport to dig out, so it works as a quick two-night city break. Prices are all-in as we found them when we checked, and they can change before you book.
The kind of trip this is
This is a city weekend built around food, architecture and museums, at an easy pace. It suits a couple or two friends who like walking from a river cruise to a gallery to a long dinner, then ending the night with live blues. Cool, gray weather is expected, so plan indoor stops and keep the lakefront for a brisk walk.
Weather in Chicago, Oct 30–Nov 1
Typical highs 51–56°F, lows near 41°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Fri, Oct 30 | 56 °F | 46 °F | Overcast |
| Sat, Oct 31 | 54 °F | 40 °F | Overcast |
| Sun, Nov 1 | 51 °F | 37 °F | Drizzle |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Chicago
Our pick is Hilton Chicago in The Loop, at $478 for the stay ($239 a night) plus a $76 property fee and rated 7.9 from 982 reviews. It's the best value and puts Millennium Park, the theaters and the city's architecture at your doorstep. The top-rated option is Hampton Inn & Suites Chicago Medical District Uic, at $538 for the stay with breakfast plus $86 in property fees and rated 9.4 from 493 reviews. It's in the Illinois Medical District. On a budget, Best Western Chicago Downtown-River North is $458 for the stay ($229 a night) plus $73 in fees and rated 7.1 from 1,922 reviews. It's the only one of the three with free cancellation, and River North is the city's nightlife core, with galleries and steakhouses.
Hilton Chicago
$478 for 2 nights, two guests · $239 a night
See roomsHampton Inn & Suites Chicago Medical District Uic
$538 for 2 nights, two guests · $269 a night
See roomsBest Western Chicago Downtown-River North
$458 for 2 nights, two guests · $229 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
- See the Bean and the fountains in Millennium Park, steps from The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend the drizzly Sunday at the Art Institute of Chicago
- Hear live blues at Kingston Mines on 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 St. Louis | St. Louis Lambert International (STL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 6h 54m (1 stop) |
| Distance | 263 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $880 |
| Hotel, 2 nights (Hilton Chicago) | $478 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,878 |
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 | $440 per person |
| Lowest in the last 30 days | $440 (Oct 16, 2026) |
| Typical price, last 60 days | $628 |
| Price checks | 14 |
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 is needed, and Chicago is on the same time as St. Louis.
- The outbound Frontier flight leaves STL at 12:14 PM and lands at ORD at 7:08 PM, with one stop.
- A checked bag is about $240 for two and isn't in the $1,434 total.
- Hilton Chicago doesn't offer free cancellation; Best Western Chicago Downtown-River North does.
- Expect highs of 51–56°F and overcast skies, with drizzle in the forecast for Sunday, Nov 1.
Questions readers ask
Is it worth it?
Yes, if you can live with the stop. The $440 per person fare is $188 below the typical fare on this route and the lowest we've seen in 30 days. The catch is a 6h 54m outbound flight with one stop.
How much is the whole trip for two?
It's $1,434 for two, all in. That covers the Frontier flights at $880 and 2 nights at Hilton Chicago at $478, plus its $76 property fee, with taxes and fees included. Checked bags, about $240 for two, and spending money aren't included.
Is there a nonstop?
Yes. When we checked, American had an 88-minute nonstop leaving at 11:31 AM and landing at 12:59 PM, at $509 per person, or $1,018 for two in flights.
What's the weather like?
It should be cool and gray. Typical highs are 51–56°F with lows near 41°F, overcast on Friday and Saturday and drizzle in the forecast for Sunday, Nov 1. Bring a jacket.
Is 2 nights enough?
It's enough for a long weekend. You land at 7:08 PM Friday, so Saturday is your full day for the river cruise, Millennium Park and blues, with Sunday morning left for the Art Institute.
Do I need a passport?
No. It's a domestic trip in US dollars, with no time difference from St. Louis.
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