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Cheap flights from Illinois to Chicago from $55

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 7/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Illinois to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:55 am - 4:00 pm
STL
-
MDW
5h 05m
1 stop
Southwest Logo
9:20 am - 10:30 am
MDW
-
STL
1h 10mnonstop
$232Southwest
Tue, Aug 18 - Thu, Aug 20
Southwest Logo
10:15 am - 3:55 pm
STL
-
MDW
5h 40m
1 stop
Southwest Logo
8:05 am - 9:30 am
MDW
-
STL
1h 25mnonstop
$233Southwest
Wed, Jul 15 - Sun, Jul 19
Frontier Logo
4:57 pm - 10:03 pm
STL
-
MDW
5h 06m
1 stop
Frontier Logo
12:11 pm - 5:37 pm
MDW
-
STL
5h 26m
1 stop
$235Frontier
Sat, Aug 1 - Tue, Aug 4
Frontier Logo
4:57 pm - 10:03 pm
STL
-
MDW
5h 06m
1 stop
Frontier Logo
6:05 am - 5:37 pm
MDW
-
STL
11h 32m
1 stop
$240Frontier
Wed, Jul 8 - Tue, Aug 4
Allegiant Air Logo
8:24 pm - 8:30 pm
PIA
-
MDW
24h 06m
1 stop
Allegiant Air Logo
9:21 pm - 3:18 pm
MDW
-
PIA
17h 57m
1 stop
$345Allegiant Air
Sun, Jul 19 - Fri, Jul 24
Allegiant Air Logo
8:24 pm - 8:31 pm
PIA
-
MDW
24h 07m
1 stop
Allegiant Air Logo
9:21 pm - 3:18 pm
MDW
-
PIA
17h 57m
1 stop
$386Allegiant Air
Thu, Jul 16 - Fri, Jul 24
Multiple Airlines Logo
11:41 am - 8:31 pm
EVV
-
MDW
8h 50m
1 stop
Multiple Airlines Logo
12:11 pm - 3:49 pm
MDW
-
EVV
27h 38m
2 stops
$411Multiple Airlines
Fri, Jul 10 - Tue, Jul 14
Multiple Airlines Logo
11:41 am - 8:31 pm
EVV
-
MDW
8h 50m
1 stop
Multiple Airlines Logo
12:11 pm - 3:49 pm
MDW
-
EVV
27h 38m
2 stops
$427Multiple Airlines
Fri, Jul 10 - Tue, Jul 14
Delta Logo
6:00 am - 10:25 pm
MLI
-
MDW
16h 25m
1 stop
Delta Logo
6:05 am - 4:22 pm
MDW
-
MLI
10h 17m
1 stop
$560Delta
Tue, Sep 29 - Sat, Oct 3
Delta Logo
6:00 am - 4:11 pm
MLI
-
MDW
10h 11m
1 stop
Delta Logo
6:05 am - 4:22 pm
MDW
-
MLI
10h 17m
1 stop
$575Delta
Mon, Sep 28 - Sat, Oct 3

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Southwest flights from Illinois to Chicago Midway Airport

Our best Southwest deals on Illinois to Chicago Midway Airport flight tickets
Southwest
Aug 18
STL10:55 amLambert-St Louis
5h 05m
1 stop
MDW4:00 pmChicago Midway
Aug 20
MDW9:20 amChicago Midway
1h 10m
STL10:30 amLambert-St Louis
$232
Southwest
Jul 15
STL10:15 amLambert-St Louis
5h 40m
1 stop
MDW3:55 pmChicago Midway
Jul 19
MDW8:05 amChicago Midway
1h 25m
STL9:30 amLambert-St Louis
$233
Southwest
Jul 11
STL4:00 pmLambert-St Louis
1h 05m
MDW5:05 pmChicago Midway
Jul 15
MDW8:20 amChicago Midway
1h 15m
STL9:35 amLambert-St Louis
$234

Frontier flights from Illinois to Chicago Midway Airport

Our best Frontier deals on Illinois to Chicago Midway Airport flight tickets
Frontier
Aug 1
STL4:57 pmLambert-St Louis
5h 06m
1 stop
MDW10:03 pmChicago Midway
Aug 4
MDW12:11 pmChicago Midway
5h 26m
1 stop
STL5:37 pmLambert-St Louis
$235
Frontier
Jul 8
STL4:57 pmLambert-St Louis
5h 06m
1 stop
MDW10:03 pmChicago Midway
Aug 4
MDW6:05 amChicago Midway
11h 32m
1 stop
STL5:37 pmLambert-St Louis
$240
Frontier
Jul 15
STL4:57 pmLambert-St Louis
5h 06m
1 stop
MDW10:03 pmChicago Midway
Jul 16
MDW12:11 pmChicago Midway
5h 26m
1 stop
STL5:37 pmLambert-St Louis
$245

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 June 22, 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
Quickest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 8/18

10:55 am-4:00 pm

1 stop5h 05m

Chicago Midway

Thu 8/20

9:20 am-10:30 am

Nonstop1h 10m

$232

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 7/15

10:15 am-3:55 pm

1 stop5h 40m

Chicago Midway

Sun 7/19

8:05 am-9:30 am

Nonstop1h 25m

$233

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/1

4:57 pm-10:03 pm

1 stop5h 06m

Chicago Midway

Tue 8/4

12:11 pm-5:37 pm

1 stop5h 26m

$235

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 7/8

4:57 pm-10:03 pm

1 stop5h 06m

Chicago Midway

Tue 8/4

6:05 am-5:37 pm

1 stop11h 32m

$240

PeoriaChicago

PIA - MDW

PIAMDW

Greater Peoria

Sun 7/19

8:24 pm-8:30 pm

1 stop24h 06m

Chicago Midway

Fri 7/24

9:21 pm-3:18 pm

1 stop17h 57m

$345

PeoriaChicago

PIA - MDW

PIAMDW

Greater Peoria

Thu 7/16

8:24 pm-8:31 pm

1 stop24h 07m

Chicago Midway

Fri 7/24

9:21 pm-3:18 pm

1 stop17h 57m

$386

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/10

11:41 am-8:31 pm

1 stop8h 50m

Chicago Midway

Tue 7/14

12:11 pm-3:49 pm

2 stops27h 38m

$411

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/10

11:41 am-8:31 pm

1 stop8h 50m

Chicago Midway

Tue 7/14

12:11 pm-3:49 pm

2 stops27h 38m

$427

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Tue 9/29

6:00 am-10:25 pm

1 stop16h 25m

Chicago Midway

Sat 10/3

6:05 am-4:22 pm

1 stop10h 17m

$560

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Mon 9/28

6:00 am-4:11 pm

1 stop10h 11m

Chicago Midway

Sat 10/3

6:05 am-4:22 pm

1 stop10h 17m

$575

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 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?

Southwest, Delta, 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.
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Frequently asked questions about flying from Illinois to Chicago Midway Airport

  • 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
Benton Harbor
Portage
Saint Joseph
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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