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Cheap flights from Missouri to Chicago from $40

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 4/11. 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

Enter your travel dates to find the best prices.
Southwest Logo
10:25 am - 11:35 am
STL
-
MDW
1h 10mnonstop
Southwest Logo
8:55 pm - 10:10 pm
MDW
-
STL
1h 15mnonstop
$117Southwest
Wed, May 6 - Wed, May 6
Southwest Logo
1:45 pm - 2:55 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
5:30 pm - 11:10 pm
MDW
-
STL
5h 40m
1 stop
$127Southwest
Wed, May 6 - Wed, May 6
Southwest Logo
2:30 pm - 8:00 pm
STL
-
MDW
5h 30m
1 stop
Southwest Logo
7:45 am - 1:00 pm
MDW
-
STL
5h 15m
1 stop
$137Southwest
Wed, May 6 - Wed, May 13
Southwest Logo
6:55 pm - 8:05 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
10:15 am - 11:30 am
MDW
-
STL
1h 15mnonstop
$144Southwest
Sat, May 2 - Tue, May 5
Frontier Logo
1:09 pm - 7:47 pm
STL
-
MDW
6h 38m
1 stop
Frontier Logo
6:05 am - 1:34 pm
MDW
-
STL
7h 29m
1 stop
$162Frontier
Fri, Mar 6 - Fri, Mar 13
Frontier Logo
8:22 pm - 3:19 pm
STL
-
MDW
18h 57m
2 stops
Frontier Logo
9:04 pm - 6:51 am
MDW
-
STL
9h 47m
1 stop
$167Frontier
Fri, Feb 27 - Sun, Mar 1
Delta Logo
5:32 pm - 10:31 pm
SGF
-
MDW
4h 59m
1 stop
Delta Logo
6:00 am - 11:08 am
MDW
-
SGF
5h 08m
1 stop
$209Delta
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
7:00 am - 9:12 pm
MCI
-
MDW
14h 12m
2 stops
Multiple Airlines Logo
2:41 pm - 5:38 pm
MDW
-
MCI
26h 57m
1 stop
$209Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
Multiple Airlines Logo
11:00 am - 10:25 pm
MCI
-
MDW
11h 25m
1 stop
Multiple Airlines Logo
9:22 pm - 3:29 pm
MDW
-
MCI
18h 07m
1 stop
$210Multiple Airlines
Fri, Feb 20 - Mon, Feb 23
Delta Logo
6:35 am - 12:29 pm
MCI
-
MDW
5h 54m
1 stop
Delta Logo
9:27 am - 1:24 pm
MDW
-
MCI
3h 57m
1 stop
$211Delta
Tue, Apr 7 - Tue, Apr 14

Southwest flights from Missouri to Chicago Midway Airport

Our best Southwest deals on Missouri to Chicago Midway Airport flight tickets
Southwest
May 6
STL3:55 pmLambert-St Louis
1h 10m
MDW5:05 pmChicago Midway
May 13
MDW8:15 amChicago Midway
1h 15m
STL9:30 amLambert-St Louis
$117
Southwest
May 6
STL1:45 pmLambert-St Louis
1h 10m
MDW2:55 pmChicago Midway
May 6
MDW5:30 pmChicago Midway
5h 40m
1 stop
STL11:10 pmLambert-St Louis
$127
Southwest
May 6
STL2:30 pmLambert-St Louis
5h 30m
1 stop
MDW8:00 pmChicago Midway
May 13
MDW7:45 amChicago Midway
5h 15m
1 stop
STL1:00 pmLambert-St Louis
$137

Delta flights from Missouri to Chicago Midway Airport

Our best Delta deals on Missouri to Chicago Midway Airport flight tickets
Delta
Mar 4
SGF5:32 pmSpringfield-Branson
4h 59m
1 stop
MDW10:31 pmChicago Midway
Mar 11
MDW6:00 amChicago Midway
5h 08m
1 stop
SGF11:08 amSpringfield-Branson
$209
Delta
Apr 7
MCI6:35 amKansas City
5h 54m
1 stop
MDW12:29 pmChicago Midway
Apr 14
MDW9:27 amChicago Midway
3h 57m
1 stop
MCI1:24 pmKansas City
$211
Delta
Mar 4
SGF5:32 pmSpringfield-Branson
4h 59m
1 stop
MDW10:31 pmChicago Midway
Mar 11
MDW9:35 amChicago Midway
8h 36m
2 stops
SGF6:11 pmSpringfield-Branson
$214

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 February 5, 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

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 5/6

10:25 am-11:35 am

Nonstop1h 10m

Chicago Midway

Wed 5/6

8:55 pm-10:10 pm

Nonstop1h 15m

$117

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 5/6

1:45 pm-2:55 pm

Nonstop1h 10m

Chicago Midway

Wed 5/6

5:30 pm-11:10 pm

1 stop5h 40m

$127

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 5/6

2:30 pm-8:00 pm

1 stop5h 30m

Chicago Midway

Wed 5/13

7:45 am-1:00 pm

1 stop5h 15m

$137

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 5/2

6:55 pm-8:05 pm

Nonstop1h 10m

Chicago Midway

Tue 5/5

10:15 am-11:30 am

Nonstop1h 15m

$144

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Fri 3/6

1:09 pm-7:47 pm

1 stop6h 38m

Chicago Midway

Fri 3/13

6:05 am-1:34 pm

1 stop7h 29m

$162

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Fri 2/27

8:22 pm-3:19 pm

2 stops18h 57m

Chicago Midway

Sun 3/1

9:04 pm-6:51 am

1 stop9h 47m

$167

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Wed 3/4

5:32 pm-10:31 pm

1 stop4h 59m

Chicago Midway

Wed 3/11

6:00 am-11:08 am

1 stop5h 08m

$209

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 3/5

7:00 am-9:12 pm

2 stops14h 12m

Chicago Midway

Thu 3/12

2:41 pm-5:38 pm

1 stop26h 57m

$209

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Fri 2/20

11:00 am-10:25 pm

1 stop11h 25m

Chicago Midway

Mon 2/23

9:22 pm-3:29 pm

1 stop18h 07m

$210

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 4/7

6:35 am-12:29 pm

1 stop5h 54m

Chicago Midway

Tue 4/14

9:27 am-1:24 pm

1 stop3h 57m

$211

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 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 $316. 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, Wednesday 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 $394.

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 $333 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $384. 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

$196

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 $196. The best round-trip flight deal from Missouri to Chicago Midway Airport found on momondo in the last 72 hours is $298.
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
4,275 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
Munster
Crown Point
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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