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Cheap flights from St. Louis 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 St. Louis 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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Frontier Logo
3:43 pm - 10:17 pmSTL-MDW
6h 34m1 stop
Frontier Logo
6:10 am - 2:48 pmMDW-STL
8h 38m1 stop
$146Frontier
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Thu, Jan 8 - Sun, Jan 11
Frontier Logo
7:43 pm - 11:08 amSTL-MDW
15h 25m1 stop
Frontier Logo
6:37 pm - 8:59 amMDW-STL
14h 22m1 stop
$148Frontier
Find Deal
Sat, Dec 6 - Sun, Dec 7
Frontier Logo
3:43 pm - 10:17 pmSTL-MDW
6h 34m1 stop
Frontier Logo
6:20 am - 6:51 amMDW-STL
24h 31m1 stop
$151Frontier
Find Deal
Thu, Jan 8 - Fri, Jan 30
Southwest Logo
4:25 pm - 5:35 pmSTL-MDW
1h 10mnonstop
Southwest Logo
1:50 pm - 3:05 pmMDW-STL
1h 15mnonstop
$156Southwest
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Thu, Jan 1 - Mon, Jan 5
Delta Logo
11:59 am - 5:19 pmSTL-MDW
5h 20m1 stop
Delta Logo
6:00 am - 12:24 pmMDW-STL
6h 24m1 stop
$157Delta
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Wed, Dec 31 - Thu, Jan 1
Frontier Logo
10:42 am - 10:12 pmSTL-MDW
11h 30m1 stop
Frontier Logo
2:49 pm - 11:07 amMDW-STL
20h 18m1 stop
$165Frontier
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Sun, Dec 7 - Wed, Dec 10
Southwest Logo
2:25 pm - 7:20 pmSTL-MDW
4h 55m1 stop
Southwest Logo
6:45 am - 8:00 amMDW-STL
1h 15mnonstop
$166Southwest
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Thu, Jan 1 - Mon, Jan 5
Frontier Logo
8:32 pm - 7:17 amSTL-MDW
10h 45m1 stop
Frontier Logo
4:19 pm - 11:33 pmMDW-STL
31h 14m2 stops
$174Frontier
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Fri, Jan 16 - Mon, Jan 19
Southwest Logo
2:25 pm - 7:20 pmSTL-MDW
4h 55m1 stop
Southwest Logo
5:40 pm - 9:30 pmMDW-STL
3h 50m1 stop
$176Southwest
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Thu, Jan 1 - Mon, Jan 5
Frontier Logo
3:30 pm - 10:12 pmSTL-MDW
30h 42m2 stops
Frontier Logo
6:15 am - 9:52 amMDW-STL
27h 37m1 stop
$177Frontier
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Thu, Dec 4 - Sun, Dec 7

Frontier flights from St. Louis to Chicago Midway Airport

Our best Frontier deals on St. Louis to Chicago Midway Airport flight tickets
Frontier
Jan 8
STL3:43 pmLambert-St Louis
6h 34m
1 stop
MDW10:17 pmChicago Midway
Jan 11
MDW6:10 amChicago Midway
8h 38m
1 stop
STL2:48 pmLambert-St Louis
$146
Find similar
Frontier
Dec 6
STL7:43 pmLambert-St Louis
15h 25m
1 stop
MDW11:08 amChicago Midway
Dec 7
MDW6:37 pmChicago Midway
14h 22m
1 stop
STL8:59 amLambert-St Louis
$148
Find similar
Frontier
Jan 8
STL3:43 pmLambert-St Louis
6h 34m
1 stop
MDW10:17 pmChicago Midway
Jan 30
MDW6:20 amChicago Midway
24h 31m
1 stop
STL6:51 amLambert-St Louis
$151
Find similar

Southwest flights from St. Louis to Chicago Midway Airport

Our best Southwest deals on St. Louis to Chicago Midway Airport flight tickets
Southwest
Jan 1
STL4:25 pmLambert-St Louis
1h 10m
MDW5:35 pmChicago Midway
Jan 5
MDW6:45 amChicago Midway
1h 15m
STL8:00 amLambert-St Louis
$156
Find similar
Southwest
Jan 1
STL4:25 pmLambert-St Louis
1h 10m
MDW5:35 pmChicago Midway
Jan 5
MDW8:00 amChicago Midway
6h 30m
1 stop
STL2:30 pmLambert-St Louis
$166
Find similar
Southwest
Nov 22
STL1:05 pmLambert-St Louis
1h 10m
MDW2:15 pmChicago Midway
Nov 24
MDW7:00 pmChicago Midway
1h 15m
STL8:15 pmLambert-St Louis
$168
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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 November 19, 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

Thu 1/8

3:43 pm-10:17 pm

1 stop6h 34m

Chicago Midway

Sun 1/11

6:10 am-2:48 pm

1 stop8h 38m

$146

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 12/6

7:43 pm-11:08 am

1 stop15h 25m

Chicago Midway

Sun 12/7

6:37 pm-8:59 am

1 stop14h 22m

$148

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

3:43 pm-10:17 pm

1 stop6h 34m

Chicago Midway

Fri 1/30

6:20 am-6:51 am

1 stop24h 31m

$151

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/1

4:25 pm-5:35 pm

Nonstop1h 10m

Chicago Midway

Mon 1/5

1:50 pm-3:05 pm

Nonstop1h 15m

$156

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 12/31

11:59 am-5:19 pm

1 stop5h 20m

Chicago Midway

Thu 1/1

6:00 am-12:24 pm

1 stop6h 24m

$157

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sun 12/7

10:42 am-10:12 pm

1 stop11h 30m

Chicago Midway

Wed 12/10

2:49 pm-11:07 am

1 stop20h 18m

$165

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/1

2:25 pm-7:20 pm

1 stop4h 55m

Chicago Midway

Mon 1/5

6:45 am-8:00 am

Nonstop1h 15m

$166

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Fri 1/16

8:32 pm-7:17 am

1 stop10h 45m

Chicago Midway

Mon 1/19

4:19 pm-11:33 pm

2 stops31h 14m

$174

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/1

2:25 pm-7:20 pm

1 stop4h 55m

Chicago Midway

Mon 1/5

5:40 pm-9:30 pm

1 stop3h 50m

$176

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 12/4

3:30 pm-10:12 pm

2 stops30h 42m

Chicago Midway

Sun 12/7

6:15 am-9:52 am

1 stop27h 37m

$177

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from St. Louis, with most prices found around $168. If you are unable to visit Chicago Midway Airport during the month of December, 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 $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 St. Louis 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 St. Louis 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 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

$158

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 $158. The best round-trip flight deal from St. Louis to Chicago Midway Airport found on momondo in the last 72 hours is $307.
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 $117Free CancellationRating
8.0
4,249 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 $325, with the best Southwest deals starting from $117 round-trip. 4,249 users have rated Southwest on momondo, with an average score of 8.0/10.

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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