$58 Find Cheap Flights from Missouri to Chicago - Compare and Save

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Cheap Flights from Missouri to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Missouri to Chicago

Mon, Nov 16 - Fri, Nov 20
Contour Logo
12:30 pm - 2:15 pmIRK  Kirksville Cannon Memorial-ORD Chicago O'Hare Intl
1h 45mnonstop
Contour Logo
2:55 pm - 4:25 pmORD  Chicago O'Hare Intl-IRK Kirksville Cannon Memorial
1h 30mnonstop
$123Contour
Sat, Nov 14 - Fri, Nov 20
Contour Logo
12:30 pm - 2:15 pmIRK  Kirksville Cannon Memorial-ORD Chicago O'Hare Intl
1h 45mnonstop
Contour Logo
2:55 pm - 4:25 pmORD  Chicago O'Hare Intl-IRK Kirksville Cannon Memorial
1h 30mnonstop
$139Contour
Sat, Dec 19 - Tue, Dec 22
Frontier Logo
5:46 pm - 12:56 amSTL  Lambert-St Louis-ORD Chicago O'Hare Intl
7h 10m1 stop Orlando
Frontier Logo
5:47 pm - 12:41 amORD  Chicago O'Hare Intl-STL Lambert-St Louis
6h 54m1 stop Orlando
$179Frontier
Wed, Dec 23 - Thu, Dec 31
Frontier Logo
5:58 pm - 12:56 amSTL  Lambert-St Louis-ORD Chicago O'Hare Intl
6h 58m1 stop Orlando
Frontier Logo
5:53 pm - 12:41 amORD  Chicago O'Hare Intl-STL Lambert-St Louis
6h 48m1 stop Orlando
$180Frontier
Mon, Dec 14 - Tue, Dec 15
Southwest Logo
8:25 pm - 9:35 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
7:35 am - 8:50 amMDW  Chicago Midway-STL Lambert-St Louis
1h 15mnonstop
$187Southwest
Mon, Dec 14 - Tue, Dec 15
Southwest Logo
2:25 pm - 3:30 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
11:45 am - 5:20 pmMDW  Chicago Midway-STL Lambert-St Louis
5h 35m1 stop Kansas City
$197Southwest
Wed, Dec 9 - Sun, Dec 13
American Airlines Logo
7:27 am - 9:00 amSTL  Lambert-St Louis-ORD Chicago O'Hare Intl
1h 33mnonstop
American Airlines Logo
11:30 am - 1:13 pmORD  Chicago O'Hare Intl-STL Lambert-St Louis
1h 43mnonstop
$203American Airlines
Thu, Dec 10 - Sun, Dec 13
American Airlines Logo
11:37 am - 12:59 pmSTL  Lambert-St Louis-ORD Chicago O'Hare Intl
1h 22mnonstop
American Airlines Logo
10:39 pm - 12:02 amORD  Chicago O'Hare Intl-STL Lambert-St Louis
1h 23mnonstop
$203American Airlines
Thu, Dec 17 - Sun, Dec 20
United Airlines Logo
5:05 am - 6:43 amSTL  Lambert-St Louis-ORD Chicago O'Hare Intl
1h 38mnonstop
United Airlines Logo
10:45 am - 12:26 pmORD  Chicago O'Hare Intl-STL Lambert-St Louis
1h 41mnonstop
$203United Airlines
Sat, Dec 5 - Sun, Dec 6
United Airlines Logo
6:55 pm - 8:25 pmSTL  Lambert-St Louis-ORD Chicago O'Hare Intl
1h 30mnonstop
United Airlines Logo
9:00 am - 10:30 amORD  Chicago O'Hare Intl-STL Lambert-St Louis
1h 30mnonstop
$203United Airlines
Useful Info

Good to know

Low season

January
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 7% increase in price.

Flights from Missouri to Chicago: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Missouri to Chicago 
Verified travelerFlew with American Airlines-May 2026
Arrive airport early, esp if checking bags - std procedure but vital here
valerieFlew with Air Canada-Jan 2025
Usually it is unreliable - always leave lots of time for connection.

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
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago