$32 Find Cheap Flights from Missouri to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$71
Overall average: $252
Southwest
Sat 1/17Tue 1/20
STL - MDW • Non-stop
Cheapest one-way
$32
Typical prices: $253-$268
Southwest
Tue 1/20
STL - MDW • Non-stop
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Flight Deals
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Flight Deals

Cheap Flights from Missouri to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Missouri to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Missouri to Chicago

Sat, Jan 17 - Tue, Jan 20
Southwest Logo
7:40 am - 8:50 amSTL-MDW
1h 10mnonstop
Southwest Logo
1:50 pm - 3:00 pmMDW-STL
1h 10mnonstop
$71Southwest
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Wed, Dec 17 - Sun, Dec 21
Contour Logo
5:30 pm - 6:50 pmUIN-ORD
1h 20mnonstop
Contour Logo
7:30 pm - 8:50 pmORD-UIN
1h 20mnonstop
$75Contour
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Tue, Jan 20 - Fri, Jan 23
United Airlines Logo
9:57 am - 11:32 amSTL-ORD
1h 35mnonstop
United Airlines Logo
10:52 am - 12:29 pmORD-STL
1h 37mnonstop
$91United Airlines
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Sat, Jan 24 - Mon, Jan 26
American Airlines Logo
6:43 pm - 8:17 pmSTL-ORD
1h 34mnonstop
American Airlines Logo
8:50 am - 10:20 amORD-STL
1h 30mnonstop
$92American Airlines
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Sat, Jan 17 - Sun, Jan 18
United Airlines Logo
11:20 am - 12:55 pmSTL-ORD
1h 35mnonstop
United Airlines Logo
1:00 pm - 2:30 pmORD-STL
1h 30mnonstop
$97United Airlines
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Mon, Jan 26 - Fri, Jan 30
Multiple Airlines Logo
5:42 pm - 1:13 pmSTL-ORD
19h 31m1 stop
Multiple Airlines Logo
12:07 pm - 2:46 pmORD-STL
26h 39m1 stop
$131Multiple Airlines
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Mon, Jan 26 - Fri, Jan 30
Frontier Logo
8:22 pm - 12:05 pmSTL-MDW
15h 43m1 stop
Frontier Logo
1:00 pm - 11:33 pmMDW-STL
10h 33m1 stop
$135Frontier
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Tue, Jan 27 - Thu, Jan 29
Multiple Airlines Logo
5:42 pm - 1:13 pmSTL-ORD
19h 31m1 stop
Multiple Airlines Logo
12:44 pm - 11:33 pmORD-STL
10h 49m1 stop
$136Multiple Airlines
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Wed, Feb 18 - Sat, Feb 21
Frontier Logo
7:43 pm - 6:46 pmSTL-ORD
23h 03m1 stop
Frontier Logo
6:00 pm - 9:47 amORD-STL
15h 47m1 stop
$138Frontier
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Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
6:00 am - 7:36 amCOU-ORD
1h 36mnonstop
American Airlines Logo
7:40 pm - 9:10 pmORD-COU
1h 30mnonstop
$180American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$32
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from St. Louis to Chicago Midway Airport

FAQs for booking flights from Missouri to Chicago

  • How does KAYAK find such low prices on flights from Missouri to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Missouri to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Missouri to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Missouri is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Missouri to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Missouri with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Missouri to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Missouri up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Missouri

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $463
Business Class flights to Chicagofrom $455
Prem Econ Class flights to Chicagofrom $726
Economy Class flights to Chicagofrom $123