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Cheap flights from St. Louis 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 St. Louis to Chicago departing on 1/13. 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 St. Louis to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:20 am - 9:30 am
STL
-
MDW
1h 10mnonstop
Southwest Logo
7:45 pm - 9:00 pm
MDW
-
STL
1h 15mnonstop
$144Southwest
Wed, Jan 21 - Thu, Jan 22
Southwest Logo
1:10 pm - 2:15 pm
STL
-
MDW
1h 05mnonstop
Southwest Logo
2:20 pm - 7:00 pm
MDW
-
STL
4h 40m1 stop
$154Southwest
Wed, Jan 21 - Thu, Jan 22
Delta Logo
5:00 pm - 10:07 pm
STL
-
MDW
5h 07m1 stop
Delta Logo
5:31 pm - 11:39 pm
MDW
-
STL
6h 08m1 stop
$157Delta
Wed, Jan 7 - Wed, Jan 14
Frontier Logo
5:11 pm - 11:09 pm
STL
-
MDW
29h 58m1 stop
Frontier Logo
4:31 pm - 10:34 pm
MDW
-
STL
30h 03m1 stop
$158Frontier
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:50 am - 1:55 pm
STL
-
MDW
7h 05m2 stops
Southwest Logo
1:50 pm - 3:00 pm
MDW
-
STL
1h 10mnonstop
$159Southwest
Wed, Jan 21 - Thu, Jan 22
Frontier Logo
5:11 pm - 11:09 pm
STL
-
MDW
29h 58m1 stop
Frontier Logo
4:31 pm - 10:34 pm
MDW
-
STL
30h 03m1 stop
$160Frontier
Thu, Jan 8 - Mon, Jan 12
Delta Logo
6:00 am - 10:27 am
STL
-
MDW
4h 27m1 stop
Delta Logo
9:32 am - 4:45 pm
MDW
-
STL
7h 13m2 stops
$162Delta
Wed, Jan 7 - Wed, Jan 14
Frontier Logo
3:43 pm - 10:17 pm
STL
-
MDW
6h 34m1 stop
Frontier Logo
4:31 pm - 10:34 pm
MDW
-
STL
30h 03m1 stop
$165Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
5:11 pm - 10:31 am
STL
-
MDW
17h 20m2 stops
Frontier Logo
9:09 pm - 2:48 pm
MDW
-
STL
17h 39m1 stop
$169Frontier
Tue, Jan 13 - Fri, Jan 16
Southwest Logo
8:20 am - 9:30 am
STL
-
MDW
1h 10mnonstop
Southwest Logo
6:10 am - 7:35 am
MDW
-
STL
1h 25mnonstop
$171Southwest
Thu, Jan 8 - Mon, Jan 12

Southwest flights from St. Louis to Chicago Midway Airport

Our best Southwest deals on St. Louis to Chicago Midway Airport flight tickets
Southwest
Jan 21
STL8:20 amLambert-St Louis
1h 10m
MDW9:30 amChicago Midway
Jan 22
MDW7:45 pmChicago Midway
1h 15m
STL9:00 pmLambert-St Louis
$144
Find similar
Southwest
Jan 21
STL1:10 pmLambert-St Louis
1h 05m
MDW2:15 pmChicago Midway
Jan 22
MDW2:20 pmChicago Midway
4h 40m
1 stop
STL7:00 pmLambert-St Louis
$154
Find similar
Southwest
Jan 21
STL6:50 amLambert-St Louis
7h 05m
2 stops
MDW1:55 pmChicago Midway
Jan 22
MDW1:50 pmChicago Midway
1h 10m
STL3:00 pmLambert-St Louis
$159
Find similar

Delta flights from St. Louis to Chicago Midway Airport

Our best Delta deals on St. Louis to Chicago Midway Airport flight tickets
Delta
Jan 7
STL5:00 pmLambert-St Louis
5h 07m
1 stop
MDW10:07 pmChicago Midway
Jan 14
MDW5:31 pmChicago Midway
6h 08m
1 stop
STL11:39 pmLambert-St Louis
$157
Find similar
Delta
Jan 7
STL6:00 amLambert-St Louis
4h 27m
1 stop
MDW10:27 amChicago Midway
Jan 14
MDW9:32 amChicago Midway
7h 13m
2 stops
STL4:45 pmLambert-St Louis
$162
Find similar
Delta
Jan 24
STL6:10 amLambert-St Louis
4h 55m
1 stop
MDW11:05 amChicago Midway
Jan 31
MDW6:25 amChicago Midway
5h 29m
1 stop
STL11:54 amLambert-St Louis
$191
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from St. Louis 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 December 11, 2025.
Use the filters below to find and compare flights from St. Louis 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 1/21

8:20 am-9:30 am

Nonstop1h 10m

Chicago Midway

Thu 1/22

7:45 pm-9:00 pm

Nonstop1h 15m

$144

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 1/21

1:10 pm-2:15 pm

Nonstop1h 05m

Chicago Midway

Thu 1/22

2:20 pm-7:00 pm

1 stop4h 40m

$154

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 1/7

5:00 pm-10:07 pm

1 stop5h 07m

Chicago Midway

Wed 1/14

5:31 pm-11:39 pm

1 stop6h 08m

$157

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

5:11 pm-11:09 pm

1 stop29h 58m

Chicago Midway

Mon 1/12

4:31 pm-10:34 pm

1 stop30h 03m

$158

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 1/21

6:50 am-1:55 pm

2 stops7h 05m

Chicago Midway

Thu 1/22

1:50 pm-3:00 pm

Nonstop1h 10m

$159

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

5:11 pm-11:09 pm

1 stop29h 58m

Chicago Midway

Mon 1/12

4:31 pm-10:34 pm

1 stop30h 03m

$160

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 1/7

6:00 am-10:27 am

1 stop4h 27m

Chicago Midway

Wed 1/14

9:32 am-4:45 pm

2 stops7h 13m

$162

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

3:43 pm-10:17 pm

1 stop6h 34m

Chicago Midway

Mon 1/12

4:31 pm-10:34 pm

1 stop30h 03m

$165

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 1/13

5:11 pm-10:31 am

2 stops17h 20m

Chicago Midway

Fri 1/16

9:09 pm-2:48 pm

1 stop17h 39m

$169

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

8:20 am-9:30 am

Nonstop1h 10m

Chicago Midway

Mon 1/12

6:10 am-7:35 am

Nonstop1h 25m

$171

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 St. Louis 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 St. Louis, with most prices found around $87. If you are unable to visit Chicago Midway Airport during the month of November, then departing from St. Louis during the month October is also very affordable. Most momondo users find prices during this month for around $237.

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 St. Louis. The lowest ticket price found for a Tuesday departure recently was $341. 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 St. Louis because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $396.

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

Flying to Chicago Midway Airport from St. Louis in the evening is the least expensive time of day to depart. momondo users have found prices as low as $350 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $399. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Lambert-St Louis to Chicago Midway flight route?

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

What cabin class options are available on Lambert-St Louis to Chicago Midway flights?

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

When to book flights from St. Louis to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from St. Louis to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap St. Louis to Chicago Midway Airport (STL to MDW) flight deals and tips

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

Best Price Found

$184

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from St. Louis in the past 72 hours is $184. The best round-trip flight deal from St. Louis to Chicago Midway Airport found on momondo in the last 72 hours is $317.
The fastest flight from St. Louis to Chicago Midway Airport takes 1h 05m
Direct flights go from St. Louis to Chicago Midway Airport every day.
Search flight deals

  • How far is Lambert-St Louis to Chicago Midway by plane?

    The distance between Lambert-St Louis and Chicago Midway is about 253.6 mi. Typically, this will take 1h 05m by plane in normal conditions.

  • When did momondo last update prices for flights from Lambert-St Louis Airport to Chicago Midway Airport?

    Prices for flights from Lambert-St Louis Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Lambert-St Louis Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Lambert-St Louis Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Lambert-St Louis Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from St. Louis to Chicago Midway Airport?

  • What is the most popular airline from St. Louis to Chicago Midway Airport?

Best airlines flying from St. Louis to Chicago Midway Airport

Compare and see reviews for airlines that fly from St. Louis to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
7.9
4,253 reviews
Search Southwest flights

  • Southwest Flights From St. Louis to Chicago Midway Airport

    Across 20 Southwest flights from St. Louis to Chicago Midway Airport this week, the average price was $307, with the best Southwest deals starting from $97 round-trip. 4,253 users have rated Southwest on momondo, with an average score of 7.9/10.

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 St. Louis to Chicago?

Finding the right flight to Chicago from St. Louis is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from St. Louis to Chicago with flexible booking policies on momondo?

Flights from St. Louis to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from St. Louis to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from St. Louis. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from St. Louis and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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