$42 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 5/25. 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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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

Sun, May 24 - Thu, May 28
Contour Logo
5:25 pm - 7:00 pm
UIN
-
ORD
1h 35mnonstop
Contour Logo
2:45 pm - 4:05 pm
ORD
-
UIN
1h 20mnonstop
$88Contour
Mon, Jun 8 - Sun, Jun 14
Contour Logo
9:55 am - 11:30 am
UIN
-
ORD
1h 35mnonstop
Contour Logo
12:20 pm - 1:40 pm
ORD
-
UIN
1h 20mnonstop
$89Contour
Thu, May 28 - Sat, Jun 6
Southwest Logo
1:45 pm - 2:55 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
6:30 am - 7:45 am
MDW
-
STL
1h 15mnonstop
$191Southwest
Sat, Aug 22 - Thu, Sep 3
American Airlines Logo
8:05 pm - 9:39 pm
STL
-
ORD
1h 34mnonstop
American Airlines Logo
11:29 am - 12:54 pm
ORD
-
STL
1h 25mnonstop
$191American Airlines
Thu, Jun 4 - Mon, Jun 8
American Airlines Logo
7:03 am - 8:30 am
STL
-
ORD
1h 27mnonstop
American Airlines Logo
11:00 pm - 12:16 am
ORD
-
STL
1h 16mnonstop
$192American Airlines
Wed, Aug 12 - Thu, Aug 13
Delta Logo
2:10 pm - 6:33 pm
STL
-
MDW
4h 23m
1 stop
Delta Logo
9:24 am - 1:14 pm
MDW
-
STL
3h 50m
1 stop
$194Delta
Tue, Jun 2 - Thu, Jun 4
Delta Logo
8:53 am - 6:05 pm
STL
-
ORD
9h 12m
2 stops
Delta Logo
6:24 am - 10:32 am
ORD
-
STL
4h 08m
1 stop
$199Delta
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
6:33 pm - 7:53 am
STL
-
ORD
13h 20m
1 stop
Frontier Logo
7:05 am - 7:23 pm
ORD
-
STL
12h 18m
2 stops
$200Frontier
Thu, May 28 - Mon, Jun 1
Southwest Logo
4:00 pm - 10:20 pm
STL
-
MDW
6h 20m
1 stop
Southwest Logo
9:30 pm - 10:45 pm
MDW
-
STL
1h 15mnonstop
$201Southwest
Mon, Jul 13 - Fri, Jul 17
Frontier Logo
4:52 pm - 7:53 am
STL
-
ORD
15h 01m
1 stop
Frontier Logo
1:50 pm - 8:57 am
ORD
-
STL
19h 07m
1 stop
$201Frontier
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$42
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Quincy to Chicago

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
SGF
-
ORD
May 2026
Arrive airport early, esp if checking bags - std procedure but vital here
valerieFlew with Air Canada
STL
-
ORD
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
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.