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.

$58 CHEAP FLIGHTS from Missouri to Chicago

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Cheap Flights from Missouri to Chicago

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

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Missouri to Chicago

Tue, Nov 10 - Sat, Nov 14

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$111Contour

Sat, Nov 14 - Sun, Dec 13

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$121Contour

Sat, Dec 5 - Sun, Dec 6

10:35 am - 5:05 pmSTL Lambert-St Louis-MDW Chicago Midway

6h 30m2 stops Baltimore/Washington Greater Rochester Intl

7:20 am - 1:25 pmMDW Chicago Midway-STL Lambert-St Louis

6h 05m1 stop Washington, D.C. Reagan-National

$162Southwest

Thu, Nov 19 - Sun, Nov 22

6:40 am - 10:39 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

3h 59m1 stop Detroit Metropolitan Wayne County

6:23 am - 12:21 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

5h 58m1 stop Minneapolis St Paul

$167Delta

Sat, Dec 5 - Sun, Dec 6

6:32 am - 10:29 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

3h 57m1 stop Detroit Metropolitan Wayne County

7:05 am - 1:30 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

6h 25m1 stop Detroit Metropolitan Wayne County

$167Delta

Thu, Nov 19 - Mon, Nov 23

7:24 pm - 12:13 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

4h 49m1 stop Atlanta Hartsfield-Jackson

10:45 am - 12:10 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 25mnonstop

$167Frontier

Thu, Nov 26 - Thu, Dec 3

5:10 am - 12:30 pmSTL Lambert-St Louis-MDW Chicago Midway

7h 20m2 stops Dallas Love Field Omaha Eppley Airfield

8:10 am - 1:45 pmMDW Chicago Midway-STL Lambert-St Louis

5h 35m1 stop Atlanta Hartsfield-Jackson

$179Southwest

Fri, Nov 20 - Mon, Nov 23

1:20 pm - 7:47 pmSTL Lambert-St Louis-MDW Chicago Midway

6h 27m1 stop Orlando

9:09 am - 5:40 pmMDW Chicago Midway-STL Lambert-St Louis

8h 31m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Wed, Dec 9 - Sun, Dec 13

7:27 am - 9:00 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 33mnonstop

11:30 am - 1:13 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 43mnonstop

$203American Airlines

Thu, Nov 19 - Mon, Nov 23

5:00 am - 6:29 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 29mnonstop

6:26 pm - 7:50 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 24mnonstop

$207American Airlines

Recent last minute flight deals from Missouri to Chicago

Tue, Nov 3 - Tue, Nov 10

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$149Contour

Sun, Nov 1 - Mon, Nov 2

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$233Contour

Wed, Nov 4 - Tue, Nov 17

4:18 pm - 12:21 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

8h 03m1 stop Denver Intl

7:35 pm - 5:42 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

22h 07m1 stop Atlanta Hartsfield-Jackson

$266Frontier

Wed, Nov 4 - Tue, Nov 17

4:18 pm - 12:21 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

8h 03m1 stop Denver Intl

7:35 pm - 5:42 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

22h 07m1 stop Atlanta Hartsfield-Jackson

$267Frontier

Mon, Nov 2 - Mon, Nov 2

7:30 am - 9:00 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 30mnonstop

8:10 pm - 9:40 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 30mnonstop

$282United Airlines

Mon, Nov 2 - Wed, Nov 25

5:34 pm - 7:05 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 31mnonstop

1:00 pm - 2:35 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 35mnonstop

$321United Airlines

Mon, Nov 2 - Wed, Nov 25

9:35 pm - 10:40 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 05mnonstop

8:00 am - 9:25 amMDW Chicago Midway-STL Lambert-St Louis

1h 25mnonstop

$321Southwest

Mon, Nov 2 - Wed, Dec 2

11:35 am - 1:00 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 25mnonstop

10:39 pm - 12:02 amORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 23mnonstop

$321American Airlines

Sun, Nov 1 - Wed, Dec 2

11:34 am - 12:59 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 25mnonstop

6:30 pm - 7:58 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 28mnonstop

$321American Airlines

Mon, Nov 2 - Wed, Nov 25

6:40 am - 1:40 pmSTL Lambert-St Louis-MDW Chicago Midway

7h 00m1 stop Baltimore/Washington

9:50 am - 11:05 amMDW Chicago Midway-STL Lambert-St Louis

1h 15mnonstop

$331Southwest

Recent direct flight deals from Missouri to Chicago

Tue, Nov 10 - Sat, Nov 14

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$111Contour

Sat, Nov 14 - Sun, Dec 13

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$121Contour

Wed, Nov 25 - Wed, Dec 2

12:30 pm - 2:15 pmIRK Kirksville Cannon Memorial-ORD Chicago O'Hare Intl

1h 45mnonstop

2:55 pm - 4:25 pmORD Chicago O'Hare Intl-IRK Kirksville Cannon Memorial

1h 30mnonstop

$132Contour

Tue, Dec 15 - Thu, Dec 17

4:40 pm - 5:50 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

11:10 am - 12:20 pmMDW Chicago Midway-STL Lambert-St Louis

1h 10mnonstop

$187Southwest

Wed, Dec 9 - Sun, Dec 13

7:27 am - 9:00 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 33mnonstop

11:30 am - 1:13 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 43mnonstop

$203American Airlines

Wed, Dec 16 - Thu, Dec 17

10:50 am - 12:25 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 35mnonstop

10:00 pm - 11:38 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 38mnonstop

$204United Airlines

Tue, Dec 15 - Thu, Dec 17

9:40 am - 11:16 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 36mnonstop

10:00 pm - 11:38 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 38mnonstop

$204United Airlines

Thu, Nov 19 - Mon, Nov 23

5:00 am - 6:29 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 29mnonstop

6:26 pm - 7:50 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 24mnonstop

$207American Airlines

Fri, Dec 18 - Sun, Dec 20

9:50 pm - 11:00 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

8:00 am - 9:25 amMDW Chicago Midway-STL Lambert-St Louis

1h 25mnonstop

$208Southwest

Fri, Nov 20 - Mon, Nov 23

1:05 pm - 2:10 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 05mnonstop

6:30 am - 7:45 amMDW Chicago Midway-STL Lambert-St Louis

1h 15mnonstop

$208Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$58

Best time to beat the crowds with an average 1% drop in price.

Most popular time to fly with an average 14% increase in price.

Flight from St. Louis to Chicago Midway Airport

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.

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.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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

Cheap Flights from Missouri to Chicago

Recent round-trip flight deals from Missouri to Chicago

Recent one-way flight deals from Missouri to Chicago

Recent last minute flight deals from Missouri to Chicago

Recent direct flight deals from Missouri to Chicago

Good to know

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High season

Cheapest flight

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

FAQs for booking flights from Missouri to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Missouri

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Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight