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

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, Oct 20 - Sat, Oct 24

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, Nov 2 - Wed, Nov 4

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, Nov 21 - Sun, Nov 22

5:30 am - 6:40 amSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

6:30 pm - 7:50 pmMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$171Southwest

Sat, Nov 21 - Sun, Nov 22

5:30 am - 6:40 amSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

8:45 am - 10:05 amMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$171Southwest

Sat, Nov 21 - Sun, Nov 22

8:12 pm - 9:48 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 36mnonstop

6:40 pm - 8:04 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 24mnonstop

$171American Airlines

Fri, Nov 6 - Tue, Nov 10

6:34 pm - 12:51 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

18h 17m1 stop Atlanta Hartsfield-Jackson

7:35 pm - 5:40 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

22h 05m1 stop Atlanta Hartsfield-Jackson

$171Frontier

Sat, Nov 21 - Sun, Nov 22

8:12 pm - 9:48 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 36mnonstop

6:40 pm - 8:04 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 24mnonstop

$172American Airlines

Sat, Nov 21 - Sun, Nov 22

6:05 pm - 12:43 amSTL Lambert-St Louis-ORD Chicago O'Hare Intl

6h 38m1 stop Orlando

5:15 am - 4:20 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

11h 05m1 stop Las Vegas Harry Reid Intl

$178Frontier

Sat, Nov 21 - Sun, Nov 22

6:40 am - 12:51 pmSTL Lambert-St Louis-MDW Chicago Midway

6h 11m1 stop Detroit Metropolitan Wayne County

9:30 am - 1:23 pmMDW Chicago Midway-STL Lambert-St Louis

3h 53m1 stop Detroit Metropolitan Wayne County

$190Delta

Sat, Nov 21 - Sun, Nov 22

6:40 am - 12:51 pmSTL Lambert-St Louis-MDW Chicago Midway

6h 11m1 stop Detroit Metropolitan Wayne County

1:31 pm - 5:14 pmMDW Chicago Midway-STL Lambert-St Louis

3h 43m1 stop Detroit Metropolitan Wayne County

$190Delta

Recent last minute flight deals from Missouri to Chicago

Tue, Oct 13 - Tue, Oct 20

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

$159Contour

Sat, Oct 10 - Mon, Oct 12

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

$300Contour

Thu, Oct 8 - Sun, Oct 11

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

27h 41m1 stop Denver Intl

3:30 pm - 11:58 amORD Chicago O'Hare Intl-MCI Kansas City

20h 28m1 stop Las Vegas Harry Reid Intl

$321Frontier

Sat, Oct 10 - Tue, Oct 13

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

Tue, Oct 13 - Wed, Oct 28

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

1h 38mnonstop

8:32 am - 10:01 amORD Chicago O'Hare Intl-COU Columbia Regional

1h 29mnonstop

$334American Airlines

Mon, Oct 12 - Sat, Oct 17

5:08 pm - 7:05 pmSGF Springfield-Branson-ORD Chicago O'Hare Intl

1h 57mnonstop

8:15 am - 10:02 amORD Chicago O'Hare Intl-SGF Springfield-Branson

1h 47mnonstop

$359American Airlines

Tue, Oct 13 - Mon, Nov 9

2:25 pm - 3:30 pmSTL Lambert-St Louis-MDW Chicago Midway

1h 05mnonstop

8:45 am - 10:05 amMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$386Southwest

Tue, Oct 13 - Mon, Nov 9

10:20 am - 2:45 pmSTL Lambert-St Louis-MDW Chicago Midway

4h 25m1 stop Columbus

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

1h 25mnonstop

$396Southwest

Sat, Oct 10 - Mon, Oct 12

3:05 pm - 4:59 pmSGF Springfield-Branson-ORD Chicago O'Hare Intl

1h 54mnonstop

9:25 pm - 11:18 pmORD Chicago O'Hare Intl-SGF Springfield-Branson

1h 53mnonstop

$411United Airlines

Sat, Oct 10 - Sun, Oct 11

11:20 am - 1:12 pmSGF Springfield-Branson-ORD Chicago O'Hare Intl

1h 52mnonstop

8:50 am - 10:45 amORD Chicago O'Hare Intl-SGF Springfield-Branson

1h 55mnonstop

$411United Airlines

Recent direct flight deals from Missouri to Chicago

Tue, Oct 20 - Sat, Oct 24

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, Nov 2 - Wed, Nov 4

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

Fri, Jan 1 - Sun, Jan 17

1:25 pm - 3:10 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

$156Contour

Sat, Nov 21 - Sun, Nov 22

8:12 pm - 9:48 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 36mnonstop

6:40 pm - 8:04 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 24mnonstop

$171American Airlines

Sat, Nov 21 - Sun, Nov 22

5:30 am - 6:40 amSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

6:30 pm - 7:50 pmMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$171Southwest

Sat, Nov 21 - Sun, Nov 22

5:30 am - 6:40 amSTL Lambert-St Louis-MDW Chicago Midway

1h 10mnonstop

8:45 am - 10:05 amMDW Chicago Midway-STL Lambert-St Louis

1h 20mnonstop

$171Southwest

Sat, Nov 21 - Sun, Nov 22

8:12 pm - 9:48 pmSTL Lambert-St Louis-ORD Chicago O'Hare Intl

1h 36mnonstop

6:40 pm - 8:04 pmORD Chicago O'Hare Intl-STL Lambert-St Louis

1h 24mnonstop

$172American Airlines

Fri, Nov 20 - Mon, Nov 23

6:01 am - 7:59 amJLN Joplin-ORD Chicago O'Hare Intl

1h 58mnonstop

7:59 am - 9:59 amORD Chicago O'Hare Intl-JLN Joplin

2h 00mnonstop

$241United Airlines

Fri, Dec 11 - Sat, Jan 16

5:01 am - 6:59 amJLN Joplin-ORD Chicago O'Hare Intl

1h 58mnonstop

7:40 am - 9:48 amORD Chicago O'Hare Intl-JLN Joplin

2h 08mnonstop

$241United Airlines

Tue, Oct 27 - Fri, Oct 30

4:14 pm - 5:59 pmMCI Kansas City-ORD Chicago O'Hare Intl

1h 45mnonstop

6:54 am - 8:42 amORD Chicago O'Hare Intl-MCI Kansas City

1h 48mnonstop

$260American Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$59

Best time to beat the crowds with an average 2% drop in price.

Most popular time to fly with an average 1% 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

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

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$59 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

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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

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Find deals for your return flight