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.

$59 CHEAP FLIGHTS from Missouri to Chicago

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Cheap Flights from Missouri to Chicago

Cheap flights from Missouri to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Sun, Oct 25 - Thu, Oct 29

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

$119Contour

Tue, Oct 27 - Sat, Oct 31

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

$120Contour

Mon, Dec 21 - Fri, Jan 1

6:05 pm - 1:09 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

7h 04m1 stop Orlando

2:31 pm - 12:41 amORD Chicago O'Hare Intl-STL Lambert-St Louis

10h 10m1 stop Orlando

$180Frontier

Fri, Dec 4 - Sun, Dec 6

12:02 pm - 7:20 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

19h 18m1 stop Atlanta Hartsfield-Jackson

10:37 pm - 11:17 amORD Chicago O'Hare Intl-STL Lambert-St Louis

12h 40m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Thu, Nov 5 - Thu, Nov 5

5:45 am - 6:55 amSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

9:25 pm - 10:50 pmMDW Chicago Midway-STL Lambert-St Louis

1h 25mnonstop

$187Southwest

Mon, Nov 2 - Tue, Nov 3

7:15 pm - 8:20 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 05mnonstop

9:40 am - 11:00 amMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$187Southwest

Fri, Nov 13 - Sun, Nov 15

5:01 am - 6:30 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 29mnonstop

10:39 pm - 11:55 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 16mnonstop

$198American Airlines

Sun, Nov 8 - Wed, Nov 11

6:00 am - 7:34 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 34mnonstop

10:39 pm - 11:59 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 20mnonstop

$198American Airlines

Sun, Nov 1 - Mon, Nov 16

1:08 pm - 2:35 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 27mnonstop

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

1h 30mnonstop

$198United Airlines

Fri, Dec 11 - Sun, Dec 13

5:25 am - 6:58 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 33mnonstop

1:10 pm - 2:41 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 31mnonstop

$198United Airlines

Thu, Oct 15 - Wed, Oct 21

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

$271Contour

Sat, Oct 17 - Sun, Oct 18

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

$292Contour

Fri, Oct 16 - Wed, Nov 18

12:53 pm - 5:16 amMCI Kansas City-ORD Chicago O'Hare Intl

16h 23m1 stop Las Vegas Harry Reid Intl

6:30 am - 7:47 pmORD Chicago O'Hare Intl-MCI Kansas City

13h 17m1 stop Denver Intl

$318Frontier

Sat, Oct 17 - Tue, Oct 20

8:43 pm - 12:24 amMCI Kansas City-ORD Chicago O'Hare Intl

27h 41m1 stop Denver Intl

6:30 am - 7:48 pmORD Chicago O'Hare Intl-MCI Kansas City

13h 18m1 stop Denver Intl

$334Frontier

Thu, Oct 15 - Wed, Nov 11

11:31 am - 12:59 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 28mnonstop

4:50 pm - 6:17 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 27mnonstop

$348American Airlines

Thu, Oct 15 - Wed, Nov 11

5:25 am - 6:30 amSTL Lambert-St Louis-MDW Chicago Midway

1h 05mnonstop

8:45 pm - 10:00 pmMDW Chicago Midway-STL Lambert-St Louis

1h 15mnonstop

$348Southwest

Tue, Oct 20 - Sat, Oct 24

6:00 am - 7:38 amCOU Columbia Regional-ORD Chicago O'Hare Intl

1h 38mnonstop

8:29 am - 9:58 amORD Chicago O'Hare Intl-COU Columbia Regional

1h 29mnonstop

$349American Airlines

Thu, Oct 15 - Wed, Nov 11

10:00 pm - 11:10 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

11:40 am - 4:45 pmMDW Chicago Midway-STL Lambert-St Louis

5h 05m1 stop Minneapolis St Paul

$358Southwest

Sat, Oct 17 - Mon, Oct 19

6:25 pm - 8:25 pmSGF Springfield-Branson-ORD Chicago O'Hare Intl

2h 00mnonstop

4:00 pm - 5:50 pmORD Chicago O'Hare Intl-SGF Springfield-Branson

1h 50mnonstop

$389United Airlines

Fri, Oct 16 - Sun, Oct 18

3:43 pm - 5:23 pmCOU Columbia Regional-ORD Chicago O'Hare Intl

1h 40mnonstop

9:00 am - 10:39 amORD Chicago O'Hare Intl-COU Columbia Regional

1h 39mnonstop

$434United Airlines

Sun, Oct 25 - Thu, Oct 29

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

$119Contour

Tue, Oct 27 - Sat, Oct 31

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

$120Contour

Thu, Oct 29 - 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

$120Contour

Thu, Nov 5 - Thu, Nov 5

5:45 am - 6:55 amSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

9:25 pm - 10:50 pmMDW Chicago Midway-STL Lambert-St Louis

1h 25mnonstop

$187Southwest

Mon, Nov 2 - Tue, Nov 3

7:15 pm - 8:20 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 05mnonstop

9:40 am - 11:00 amMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$187Southwest

Mon, Nov 16 - Thu, Nov 19

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

1h 10mnonstop

7:35 am - 8:50 amMDW Chicago Midway-STL Lambert-St Louis

1h 15mnonstop

$187Southwest

Fri, Nov 13 - Sun, Nov 15

5:01 am - 6:30 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 29mnonstop

10:39 pm - 11:55 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 16mnonstop

$198American Airlines

Sun, Nov 8 - Wed, Nov 11

6:00 am - 7:34 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 34mnonstop

10:39 pm - 11:59 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 20mnonstop

$198American Airlines

Sun, Dec 13 - Thu, Dec 31

1:18 pm - 2:47 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 29mnonstop

7:51 pm - 9:22 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 31mnonstop

$198United Airlines

Sun, Nov 1 - Mon, Nov 16

1:08 pm - 2:35 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 27mnonstop

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

1h 30mnonstop

$198United Airlines

Low season	January
High season	June
Cheapest flight	$59

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

Most popular time to fly with an average 9% 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.