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Cheap flights from Illinois 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 Illinois to Chicago departing on 5/20. 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.
Frontier Logo
11:21 am - 8:07 pm
STL
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 5:34 pm
MDW
-
STL
11h 34m
1 stop
$180Frontier
Tue, Apr 7 - Thu, Apr 9
Frontier Logo
11:25 am - 7:31 pm
STL
-
MDW
8h 06m
1 stop
Frontier Logo
2:00 pm - 11:19 pm
MDW
-
STL
9h 19m
1 stop
$181Frontier
Thu, Apr 16 - Sun, Apr 26
Southwest Logo
5:40 am - 6:50 am
STL
-
MDW
1h 10mnonstop
Southwest Logo
7:50 am - 9:05 am
MDW
-
STL
1h 15mnonstop
$191Southwest
Sat, Apr 11 - Mon, Apr 13
Southwest Logo
10:15 am - 3:50 pm
STL
-
MDW
5h 35m
1 stop
Southwest Logo
9:00 am - 10:15 am
MDW
-
STL
1h 15mnonstop
$201Southwest
Thu, Apr 16 - Thu, Apr 23
Frontier Logo
4:59 pm - 11:05 pm
STL
-
MDW
6h 06m
1 stop
Frontier Logo
5:30 am - 11:25 pm
MDW
-
STL
17h 55m
1 stop
$205Frontier
Sat, Apr 11 - Mon, Apr 13
Southwest Logo
10:55 am - 5:10 pm
STL
-
MDW
6h 15m
2 stops
Southwest Logo
9:15 am - 10:30 am
MDW
-
STL
1h 15mnonstop
$206Southwest
Sat, Apr 18 - Sat, Apr 25
Delta Logo
11:42 am - 4:26 pm
STL
-
MDW
4h 44m
1 stop
Delta Logo
6:00 am - 11:56 am
MDW
-
STL
5h 56m
1 stop
$211Delta
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
7:46 pm - 8:07 pm
EVV
-
MDW
24h 21m
2 stops
Multiple Airlines Logo
5:30 am - 7:06 pm
MDW
-
EVV
13h 36m
1 stop
$568Multiple Airlines
Mon, Apr 6 - Fri, Apr 10
Multiple Airlines Logo
7:46 pm - 10:19 pm
EVV
-
MDW
26h 33m
2 stops
Multiple Airlines Logo
5:30 am - 7:06 pm
MDW
-
EVV
13h 36m
1 stop
$585Multiple Airlines
Mon, Apr 6 - Fri, Apr 10
Delta Logo
5:59 pm - 10:31 pm
EVV
-
MDW
4h 32m
1 stop
Delta Logo
10:45 am - 5:18 pm
MDW
-
EVV
6h 33m
1 stop
$1,463Delta
Thu, Apr 9 - Sun, Apr 12

Frontier flights from Illinois to Chicago Midway Airport

Our best Frontier deals on Illinois to Chicago Midway Airport flight tickets
Frontier
Apr 7
STL11:21 amLambert-St Louis
8h 46m
1 stop
MDW8:07 pmChicago Midway
Apr 9
MDW6:00 amChicago Midway
11h 34m
1 stop
STL5:34 pmLambert-St Louis
$180
Frontier
Apr 16
STL11:25 amLambert-St Louis
8h 06m
1 stop
MDW7:31 pmChicago Midway
Apr 26
MDW2:00 pmChicago Midway
9h 19m
1 stop
STL11:19 pmLambert-St Louis
$181
Frontier
Apr 11
STL4:59 pmLambert-St Louis
6h 06m
1 stop
MDW11:05 pmChicago Midway
Apr 13
MDW5:30 amChicago Midway
17h 55m
1 stop
STL11:25 pmLambert-St Louis
$205

Southwest flights from Illinois to Chicago Midway Airport

Our best Southwest deals on Illinois to Chicago Midway Airport flight tickets
Southwest
Apr 9
STL7:20 amLambert-St Louis
1h 10m
MDW8:30 amChicago Midway
Apr 13
MDW9:00 amChicago Midway
1h 15m
STL10:15 amLambert-St Louis
$191
Southwest
Apr 16
STL10:15 amLambert-St Louis
5h 35m
1 stop
MDW3:50 pmChicago Midway
Apr 23
MDW9:00 amChicago Midway
1h 15m
STL10:15 amLambert-St Louis
$201
Southwest
Apr 18
STL10:55 amLambert-St Louis
6h 15m
2 stops
MDW5:10 pmChicago Midway
Apr 25
MDW9:15 amChicago Midway
1h 15m
STL10:30 amLambert-St Louis
$206

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 March 24, 2026.
Use the filters below to find and compare flights from Illinois to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 4/7

11:21 am-8:07 pm

1 stop8h 46m

Chicago Midway

Thu 4/9

6:00 am-5:34 pm

1 stop11h 34m

$180

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 4/16

11:25 am-7:31 pm

1 stop8h 06m

Chicago Midway

Sun 4/26

2:00 pm-11:19 pm

1 stop9h 19m

$181
Quickest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 4/11

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Mon 4/13

7:50 am-9:05 am

Nonstop1h 15m

$191

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 4/16

10:15 am-3:50 pm

1 stop5h 35m

Chicago Midway

Thu 4/23

9:00 am-10:15 am

Nonstop1h 15m

$201

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 4/11

4:59 pm-11:05 pm

1 stop6h 06m

Chicago Midway

Mon 4/13

5:30 am-11:25 pm

1 stop17h 55m

$205

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 4/18

10:55 am-5:10 pm

2 stops6h 15m

Chicago Midway

Sat 4/25

9:15 am-10:30 am

Nonstop1h 15m

$206

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 4/18

11:42 am-4:26 pm

1 stop4h 44m

Chicago Midway

Sat 4/25

6:00 am-11:56 am

1 stop5h 56m

$211

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 4/6

7:46 pm-8:07 pm

2 stops24h 21m

Chicago Midway

Fri 4/10

5:30 am-7:06 pm

1 stop13h 36m

$568

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 4/6

7:46 pm-10:19 pm

2 stops26h 33m

Chicago Midway

Fri 4/10

5:30 am-7:06 pm

1 stop13h 36m

$585

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 4/9

5:59 pm-10:31 pm

1 stop4h 32m

Chicago Midway

Sun 4/12

10:45 am-5:18 pm

1 stop6h 33m

$1,463

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Illinois 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 airline that flies from Illinois to Chicago Midway?

Delta, Southwest, and Allegiant Air are the most popular carriers operating from Illinois to Chicago Midway

Cheap Illinois to Chicago Midway Airport flight deals and tips

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

Fastest flight time

1h 05m

Direct flights

Every day
The fastest flight from Illinois to Chicago Midway Airport takes 1h 05m
Direct flights go from Illinois to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Illinois to Chicago Midway Airport?

    Prices for flights from Illinois to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Illinois to Chicago Midway Airport?

  • How old do you have to be to fly from Illinois to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Illinois 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 Illinois.

Can I find flights from Illinois to Chicago with flexible booking policies on momondo?

Flights from Illinois 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 Illinois to Chicago?

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

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

Of course. momondo tracks the price of Illinois to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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