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Cheap flights from Missouri to Chicago from $49

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 12/24. 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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Cheap round-trip flights

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Southwest Logo
7:35 pm - 8:45 pmSTL-MDW
1h 10mnonstop
Southwest Logo
6:20 am - 7:35 amMDW-STL
1h 15mnonstop
$101Southwest
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Wed, Dec 10 - Mon, Dec 15
Frontier Logo
12:04 pm - 10:12 pmSTL-MDW
10h 08m1 stop
Frontier Logo
3:10 pm - 10:33 pmMDW-STL
7h 23m1 stop
$110Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
12:04 pm - 6:08 pmSTL-MDW
6h 04m1 stop
Frontier Logo
3:10 pm - 10:33 pmMDW-STL
7h 23m1 stop
$111Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
10:15 am - 11:25 amSTL-MDW
1h 10mnonstop
Southwest Logo
9:05 pm - 10:20 pmMDW-STL
1h 15mnonstop
$117Southwest
Find Deal
Tue, Dec 16 - Tue, Dec 16
Southwest Logo
6:15 pm - 10:35 pmSTL-MDW
4h 20m1 stop
Southwest Logo
9:50 am - 1:00 pmMDW-STL
3h 10m1 stop
$121Southwest
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Wed, Dec 10 - Mon, Dec 15
Southwest Logo
7:00 am - 8:10 amSTL-MDW
1h 10mnonstop
Southwest Logo
11:25 am - 5:25 pmMDW-STL
6h 00m1 stop
$127Southwest
Find Deal
Tue, Dec 16 - Tue, Dec 16
Southwest Logo
8:20 am - 9:30 amSTL-MDW
1h 10mnonstop
Southwest Logo
1:20 pm - 8:35 pmMDW-STL
7h 15m2 stops
$132Southwest
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Tue, Feb 3 - Tue, Feb 3
Delta Logo
5:28 pm - 11:47 pmSTL-MDW
6h 19m1 stop
Delta Logo
10:49 am - 4:21 pmMDW-STL
5h 32m1 stop
$157Delta
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Wed, Dec 3 - Wed, Dec 10
Delta Logo
6:00 am - 12:34 pmSTL-MDW
6h 34m2 stops
Delta Logo
7:02 pm - 11:29 pmMDW-STL
4h 27m1 stop
$162Delta
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Tue, Dec 16 - Tue, Dec 16
Allegiant Air Logo
5:55 pm - 9:32 amSGF-MDW
15h 37m1 stop
Allegiant Air Logo
3:14 pm - 8:03 amMDW-SGF
16h 49m2 stops
$944Allegiant Air
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Fri, Nov 28 - Sun, Nov 30

Frontier flights from Missouri to Chicago Midway Airport

Our best Frontier deals on Missouri to Chicago Midway Airport flight tickets
Frontier
Dec 4
STL12:04 pmLambert-St Louis
10h 08m
1 stop
MDW10:12 pmChicago Midway
Dec 8
MDW3:10 pmChicago Midway
7h 23m
1 stop
STL10:33 pmLambert-St Louis
$110
Find similar
Frontier
Dec 4
STL12:04 pmLambert-St Louis
6h 04m
1 stop
MDW6:08 pmChicago Midway
Dec 8
MDW3:10 pmChicago Midway
7h 23m
1 stop
STL10:33 pmLambert-St Louis
$111
Find similar
Frontier
Dec 11
STL12:04 pmLambert-St Louis
6h 04m
1 stop
MDW6:08 pmChicago Midway
Dec 14
MDW6:15 amChicago Midway
27h 37m
1 stop
STL9:52 amLambert-St Louis
$135
Find similar

Southwest flights from Missouri to Chicago Midway Airport

Our best Southwest deals on Missouri to Chicago Midway Airport flight tickets
Southwest
Dec 10
STL7:35 pmLambert-St Louis
1h 10m
MDW8:45 pmChicago Midway
Dec 15
MDW6:20 amChicago Midway
1h 15m
STL7:35 amLambert-St Louis
$101
Find similar
Southwest
Dec 16
STL10:15 amLambert-St Louis
1h 10m
MDW11:25 amChicago Midway
Dec 16
MDW9:05 pmChicago Midway
1h 15m
STL10:20 pmLambert-St Louis
$117
Find similar
Southwest
Dec 10
STL6:15 pmLambert-St Louis
4h 20m
1 stop
MDW10:35 pmChicago Midway
Dec 15
MDW9:50 amChicago Midway
3h 10m
1 stop
STL1:00 pmLambert-St Louis
$121
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 November 6, 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

Wed 12/10

7:35 pm-8:45 pm

Nonstop1h 10m

Chicago Midway

Mon 12/15

6:20 am-7:35 am

Nonstop1h 15m

$101

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 12/4

12:04 pm-10:12 pm

1 stop10h 08m

Chicago Midway

Mon 12/8

3:10 pm-10:33 pm

1 stop7h 23m

$110

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 12/4

12:04 pm-6:08 pm

1 stop6h 04m

Chicago Midway

Mon 12/8

3:10 pm-10:33 pm

1 stop7h 23m

$111

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 12/16

10:15 am-11:25 am

Nonstop1h 10m

Chicago Midway

Tue 12/16

9:05 pm-10:20 pm

Nonstop1h 15m

$117

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 12/10

6:15 pm-10:35 pm

1 stop4h 20m

Chicago Midway

Mon 12/15

9:50 am-1:00 pm

1 stop3h 10m

$121

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 12/16

7:00 am-8:10 am

Nonstop1h 10m

Chicago Midway

Tue 12/16

11:25 am-5:25 pm

1 stop6h 00m

$127

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 2/3

8:20 am-9:30 am

Nonstop1h 10m

Chicago Midway

Tue 2/3

1:20 pm-8:35 pm

2 stops7h 15m

$132

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 12/3

5:28 pm-11:47 pm

1 stop6h 19m

Chicago Midway

Wed 12/10

10:49 am-4:21 pm

1 stop5h 32m

$157

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 12/16

6:00 am-12:34 pm

2 stops6h 34m

Chicago Midway

Tue 12/16

7:02 pm-11:29 pm

1 stop4h 27m

$162

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Fri 11/28

5:55 pm-9:32 am

1 stop15h 37m

Chicago Midway

Sun 11/30

3:14 pm-8:03 am

2 stops16h 49m

$944

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, Tuesday is the cheapest day to fly to Chicago Midway Airport from Missouri. The lowest ticket price found for a Tuesday departure recently was $355. 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 $407.

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 $360 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $397. 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 is only 1 cabin class 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

$158

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 $158. The best round-trip flight deal from Missouri to Chicago Midway Airport found on momondo in the last 72 hours is $290.
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 $117Free CancellationRating
8.0
4,241 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
Portage
Lansing
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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