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Cheap flights from Missouri to Chicago from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Missouri to Chicago departing on 7/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Missouri to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:50 pm - 10:00 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
5:50 pm - 7:05 pm
MDW
-
STL
1h 15mnonstop
$227Southwest
Sat, Aug 1 - Fri, Aug 7
Southwest Logo
8:50 pm - 10:00 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
12:05 pm - 5:20 pm
MDW
-
STL
5h 15m
1 stop
$237Southwest
Sat, Aug 1 - Fri, Aug 7
Southwest Logo
1:30 pm - 2:35 pm
STL
-
MDW
1h 05mnonstop
Southwest Logo
5:10 pm - 6:20 pm
MDW
-
STL
1h 10mnonstop
$238Southwest
Sun, Jul 19 - Tue, Jul 21
Frontier Logo
6:34 pm - 11:07 am
STL
-
MDW
16h 33m
1 stop
Frontier Logo
6:05 am - 5:37 pm
MDW
-
STL
11h 32m
1 stop
$242Frontier
Tue, Jul 21 - Thu, Jul 23
Southwest Logo
6:45 am - 1:05 pm
STL
-
MDW
6h 20m
2 stops
Southwest Logo
5:30 pm - 10:05 pm
MDW
-
STL
4h 35m
1 stop
$243Southwest
Sat, Aug 8 - Mon, Aug 10
Frontier Logo
4:57 pm - 10:03 pm
STL
-
MDW
5h 06m
1 stop
Frontier Logo
6:05 am - 5:37 pm
MDW
-
STL
11h 32m
1 stop
$244Frontier
Wed, Jul 29 - Sun, Aug 2
Frontier Logo
4:57 pm - 10:03 pm
STL
-
MDW
5h 06m
1 stop
Frontier Logo
6:05 am - 5:37 pm
MDW
-
STL
11h 32m
1 stop
$245Frontier
Wed, Jul 22 - Sun, Jul 26
Delta Logo
5:40 pm - 10:25 pm
SGF
-
MDW
4h 45m
1 stop
Delta Logo
4:25 pm - 9:19 pm
MDW
-
SGF
4h 54m
1 stop
$269Delta
Thu, Oct 29 - Sat, Oct 31
Delta Logo
3:22 pm - 10:25 pm
SGF
-
MDW
7h 03m
1 stop
Delta Logo
1:28 pm - 9:19 pm
MDW
-
SGF
7h 51m
2 stops
$274Delta
Thu, Oct 29 - Sat, Oct 31
Multiple Airlines Logo
8:51 pm - 8:31 pm
SGF
-
MDW
23h 40m
1 stop
Multiple Airlines Logo
6:05 am - 12:31 pm
MDW
-
SGF
30h 26m
2 stops
$401Multiple Airlines
Thu, Jul 30 - Thu, Aug 6

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Southwest flights from Missouri to Chicago Midway Airport

Our best Southwest deals on Missouri to Chicago Midway Airport flight tickets
Southwest
Aug 1
STL8:50 pmLambert-St Louis
1h 10m
MDW10:00 pmChicago Midway
Aug 7
MDW5:50 pmChicago Midway
1h 15m
STL7:05 pmLambert-St Louis
$227
Southwest
Aug 1
STL8:50 pmLambert-St Louis
1h 10m
MDW10:00 pmChicago Midway
Aug 7
MDW12:05 pmChicago Midway
5h 15m
1 stop
STL5:20 pmLambert-St Louis
$237
Southwest
Jul 19
STL1:30 pmLambert-St Louis
1h 05m
MDW2:35 pmChicago Midway
Jul 21
MDW5:10 pmChicago Midway
1h 10m
STL6:20 pmLambert-St Louis
$238

Delta flights from Missouri to Chicago Midway Airport

Our best Delta deals on Missouri to Chicago Midway Airport flight tickets
Delta
Sep 27
STL6:40 amLambert-St Louis
5h 59m
1 stop
MDW12:39 pmChicago Midway
Oct 3
MDW9:29 amChicago Midway
5h 45m
1 stop
STL3:14 pmLambert-St Louis
$257
Delta
Oct 29
SGF5:40 pmSpringfield-Branson
4h 45m
1 stop
MDW10:25 pmChicago Midway
Oct 31
MDW4:25 pmChicago Midway
4h 54m
1 stop
SGF9:19 pmSpringfield-Branson
$269
Delta
Oct 29
SGF3:22 pmSpringfield-Branson
7h 03m
1 stop
MDW10:25 pmChicago Midway
Oct 31
MDW1:28 pmChicago Midway
7h 51m
2 stops
SGF9:19 pmSpringfield-Branson
$274

momondo Fare Finder

 
Customize your flight search to find flights from Missouri to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 1, 2026.
Use the filters below to find and compare flights from Missouri to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/1

8:50 pm-10:00 pm

Nonstop1h 10m

Chicago Midway

Fri 8/7

5:50 pm-7:05 pm

Nonstop1h 15m

$227

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/1

8:50 pm-10:00 pm

Nonstop1h 10m

Chicago Midway

Fri 8/7

12:05 pm-5:20 pm

1 stop5h 15m

$237
Quickest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sun 7/19

1:30 pm-2:35 pm

Nonstop1h 05m

Chicago Midway

Tue 7/21

5:10 pm-6:20 pm

Nonstop1h 10m

$238

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 7/21

6:34 pm-11:07 am

1 stop16h 33m

Chicago Midway

Thu 7/23

6:05 am-5:37 pm

1 stop11h 32m

$242

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/8

6:45 am-1:05 pm

2 stops6h 20m

Chicago Midway

Mon 8/10

5:30 pm-10:05 pm

1 stop4h 35m

$243

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 7/29

4:57 pm-10:03 pm

1 stop5h 06m

Chicago Midway

Sun 8/2

6:05 am-5:37 pm

1 stop11h 32m

$244

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 7/22

4:57 pm-10:03 pm

1 stop5h 06m

Chicago Midway

Sun 7/26

6:05 am-5:37 pm

1 stop11h 32m

$245

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 10/29

5:40 pm-10:25 pm

1 stop4h 45m

Chicago Midway

Sat 10/31

4:25 pm-9:19 pm

1 stop4h 54m

$269

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 10/29

3:22 pm-10:25 pm

1 stop7h 03m

Chicago Midway

Sat 10/31

1:28 pm-9:19 pm

2 stops7h 51m

$274

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 7/30

8:51 pm-8:31 pm

1 stop23h 40m

Chicago Midway

Thu 8/6

6:05 am-12:31 pm

2 stops30h 26m

$401

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Missouri to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Missouri, with most prices found around $77. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Missouri during the month July is also very affordable. Most momondo users find prices during this month for around $94.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Missouri. The lowest ticket price found for a Saturday departure recently was $386. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Missouri because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $499.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Missouri at noon is the least expensive time of day to depart. momondo users have found prices as low as $356 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $448. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Missouri to Chicago Midway flight route?

Fly from Lambert-St Louis to Chicago Midway for the best Missouri - Chicago Midway flight prices

What cabin class options are available on Missouri to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Missouri to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Missouri to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Missouri to Chicago Midway Airport.

Cheap Missouri to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Missouri to Chicago Midway Airport

Best Price Found

$200

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Missouri in the past 72 hours is $200. The best round-trip flight deal from Missouri to Chicago Midway Airport found on momondo in the last 72 hours is $346.
The fastest flight from Missouri to Chicago Midway Airport takes 1h 05m
Direct flights go from Missouri to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Missouri to Chicago Midway Airport

  • When did momondo last update prices for flights from Missouri to Chicago Midway Airport?

    Prices for flights from Missouri to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Missouri to Chicago Midway Airport?

  • How old do you have to be to fly from Missouri to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Missouri to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Missouri to Chicago Midway Airport?

Best airlines flying from Missouri to Chicago Midway Airport

Compare and see reviews for airlines that fly from Missouri to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $137Free CancellationRating
7.9
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Missouri to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Missouri.

Can I find flights from Missouri to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Missouri with this policy.

How can momondo help me find flights from Missouri to Chicago?

Once you have performed a search for Missouri to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Missouri to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Missouri to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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