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Cheap flights from Missouri to Chicago from $39

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 10/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Missouri to Chicago

Cheap round-trip flights

Southwest Logo
6:00 pm - 7:05 pmSTL-MDW
1h 05mnonstop
Southwest Logo
11:45 am - 12:55 pmMDW-STL
1h 10mnonstop
$77Southwest
Find Deal
Sat, Sep 13 - Mon, Sep 15
Southwest Logo
8:30 am - 3:45 pmSTL-MDW
7h 15m1 stop
Southwest Logo
11:45 am - 12:55 pmMDW-STL
1h 10mnonstop
$87Southwest
Find Deal
Sat, Sep 13 - Mon, Sep 15
Southwest Logo
7:15 am - 1:30 pmSTL-MDW
6h 15m2 stops
Southwest Logo
8:25 pm - 9:40 pmMDW-STL
1h 15mnonstop
$92Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 23
Southwest Logo
6:50 pm - 10:50 pmSTL-MDW
4h 00m1 stop
Southwest Logo
9:50 am - 2:15 pmMDW-STL
4h 25m1 stop
$97Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 6
Southwest Logo
7:15 am - 1:30 pmSTL-MDW
6h 15m2 stops
Southwest Logo
3:00 pm - 7:50 pmMDW-STL
4h 50m1 stop
$102Southwest
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Sat, Sep 13 - Tue, Sep 23
Frontier Logo
5:15 pm - 11:20 pmMCI-MDW
6h 05m1 stop
Frontier Logo
6:20 am - 4:20 pmMDW-MCI
10h 00m1 stop
$144Frontier
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Fri, Oct 3 - Mon, Oct 6
Frontier Logo
4:00 pm - 11:20 pmSTL-MDW
7h 20m1 stop
Frontier Logo
6:20 am - 3:04 pmMDW-STL
8h 44m1 stop
$144Frontier
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Thu, Sep 11 - Thu, Sep 18
Delta Logo
3:55 pm - 9:10 pmSTL-MDW
5h 15m1 stop
Delta Logo
6:00 am - 12:21 pmMDW-STL
6h 21m1 stop
$177Delta
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Sat, Sep 13 - Tue, Sep 16
Delta Logo
3:36 pm - 9:26 pmSTL-MDW
5h 50m1 stop
Delta Logo
6:30 pm - 11:24 pmMDW-STL
4h 54m1 stop
$208Delta
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Wed, Sep 3 - Mon, Sep 22
Logo
9:29 am - 12:44 pmSGF-MDW
27h 15m1 stop
Logo
10:13 am - 9:51 amMDW-SGF
23h 38m1 stop
$318
Find Deal
Thu, Sep 11 - Sun, Sep 14

Southwest flights from Missouri to Chicago Midway Airport

Our best Southwest deals on Missouri to Chicago Midway Airport flight tickets
Southwest
Sep 13
STL6:00 pmLambert-St Louis
1h 05m
MDW7:05 pmChicago Midway
Sep 15
MDW11:45 amChicago Midway
1h 10m
STL12:55 pmLambert-St Louis
$77
Find similar
Southwest
Sep 13
STL8:30 amLambert-St Louis
7h 15m
1 stop
MDW3:45 pmChicago Midway
Sep 15
MDW11:45 amChicago Midway
1h 10m
STL12:55 pmLambert-St Louis
$87
Find similar
Southwest
Sep 13
STL7:15 amLambert-St Louis
6h 15m
2 stops
MDW1:30 pmChicago Midway
Sep 23
MDW8:25 pmChicago Midway
1h 15m
STL9:40 pmLambert-St Louis
$92
Find similar

Delta flights from Missouri to Chicago Midway Airport

Our best Delta deals on Missouri to Chicago Midway Airport flight tickets
Delta
Sep 13
STL3:55 pmLambert-St Louis
5h 15m
1 stop
MDW9:10 pmChicago Midway
Sep 16
MDW6:00 amChicago Midway
6h 21m
1 stop
STL12:21 pmLambert-St Louis
$177
Find similar
Delta
Sep 3
STL3:36 pmLambert-St Louis
5h 50m
1 stop
MDW9:26 pmChicago Midway
Sep 22
MDW6:30 pmChicago Midway
4h 54m
1 stop
STL11:24 pmLambert-St Louis
$208
Find similar
Delta
Sep 16
SGF6:00 amSpringfield-Branson
5h 48m
1 stop
MDW11:48 amChicago Midway
Sep 20
MDW4:25 pmChicago Midway
5h 37m
1 stop
SGF10:02 pmSpringfield-Branson
$209
Find similar

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 August 14, 2025.
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

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

6:00 pm-7:05 pm

Nonstop1h 05m

Chicago Midway

Mon 9/15

11:45 am-12:55 pm

Nonstop1h 10m

$77

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

8:30 am-3:45 pm

1 stop7h 15m

Chicago Midway

Mon 9/15

11:45 am-12:55 pm

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

7:15 am-1:30 pm

2 stops6h 15m

Chicago Midway

Tue 9/23

8:25 pm-9:40 pm

Nonstop1h 15m

$92

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/4

6:50 pm-10:50 pm

1 stop4h 00m

Chicago Midway

Sat 9/6

9:50 am-2:15 pm

1 stop4h 25m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

7:15 am-1:30 pm

2 stops6h 15m

Chicago Midway

Tue 9/23

3:00 pm-7:50 pm

1 stop4h 50m

$102

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Fri 10/3

5:15 pm-11:20 pm

1 stop6h 05m

Chicago Midway

Mon 10/6

6:20 am-4:20 pm

1 stop10h 00m

$144

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/11

4:00 pm-11:20 pm

1 stop7h 20m

Chicago Midway

Thu 9/18

6:20 am-3:04 pm

1 stop8h 44m

$144

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

3:55 pm-9:10 pm

1 stop5h 15m

Chicago Midway

Tue 9/16

6:00 am-12:21 pm

1 stop6h 21m

$177

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 9/3

3:36 pm-9:26 pm

1 stop5h 50m

Chicago Midway

Mon 9/22

6:30 pm-11:24 pm

1 stop4h 54m

$208

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 9/11

9:29 am-12:44 pm

1 stop27h 15m

Chicago Midway

Sun 9/14

10:13 am-9:51 am

1 stop23h 38m

$318

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from Missouri, with most prices found around $243. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Missouri during the month January is also very affordable. Most momondo users find prices during this month for around $252.

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 $370. 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 $421.

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

Flying to Chicago Midway Airport from Missouri in the evening is the least expensive time of day to depart. momondo users have found prices as low as $347 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $387. 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 flights?

There are 1 cabin classes available to choose from on Missouri to Chicago Midway 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

$39

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 $39. The best round-trip flight deal from Missouri to Chicago Midway Airport found on momondo in the last 72 hours is $77.
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

  • 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 $151Free CancellationRating
8.0
4,244 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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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