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Cheap flights from Illinois 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 Illinois 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
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
Multiple Airlines Logo
7:46 pm - 2:55 pm
EVV
-
MDW
19h 09m
1 stop
Multiple Airlines Logo
9:04 pm - 7:06 pm
MDW
-
EVV
22h 02m
2 stops
$484Multiple Airlines
Fri, Feb 13 - Sun, Feb 15
Delta Logo
6:00 am - 10:31 pm
MLI
-
MDW
16h 31m
1 stop
Delta Logo
10:45 am - 10:30 pm
MDW
-
MLI
11h 45m
1 stop
$587Delta
Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
12:41 pm - 9:28 am
PIA
-
MDW
20h 47m
1 stop
Multiple Airlines Logo
3:21 pm - 7:51 pm
MDW
-
PIA
28h 30m
2 stops
$620Multiple Airlines
Wed, Feb 18 - Sun, Feb 22
Allegiant Air Logo
11:28 am - 8:34 am
MLI
-
MDW
21h 06m
1 stop
Allegiant Air Logo
1:04 pm - 4:33 pm
MDW
-
MLI
27h 29m
1 stop
$691Allegiant Air
Wed, Mar 11 - Tue, Mar 17
Allegiant Air Logo
11:28 am - 8:34 am
MLI
-
MDW
21h 06m
1 stop
Allegiant Air Logo
9:24 am - 9:08 am
MDW
-
MLI
23h 44m
1 stop
$718Allegiant Air
Wed, Mar 11 - Sun, Mar 15
Delta Logo
6:00 am - 10:21 am
EVV
-
MDW
4h 21m
1 stop
Delta Logo
9:35 am - 5:18 pm
MDW
-
EVV
7h 43m
2 stops
$1,368Delta
Sat, Mar 7 - Sun, Mar 8

Southwest flights from Illinois to Chicago Midway Airport

Our best Southwest deals on Illinois 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 Illinois to Chicago Midway Airport

Our best Delta deals on Illinois to Chicago Midway Airport flight tickets
Delta
Apr 22
STL6:20 amLambert-St Louis
6h 23m
2 stops
MDW12:43 pmChicago Midway
Apr 24
MDW7:16 pmChicago Midway
3h 57m
1 stop
STL11:13 pmLambert-St Louis
$231
Delta
May 10
STL6:00 amLambert-St Louis
5h 56m
1 stop
MDW11:56 amChicago Midway
May 11
MDW5:14 pmChicago Midway
6h 45m
1 stop
STL11:59 pmLambert-St Louis
$264
Delta
May 10
STL6:20 amLambert-St Louis
6h 22m
2 stops
MDW12:42 pmChicago Midway
May 11
MDW5:14 pmChicago Midway
6h 45m
1 stop
STL11:59 pmLambert-St Louis
$269

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 February 5, 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

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

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

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 2/13

7:46 pm-2:55 pm

1 stop19h 09m

Chicago Midway

Sun 2/15

9:04 pm-7:06 pm

2 stops22h 02m

$484

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Tue 3/10

6:00 am-10:31 pm

1 stop16h 31m

Chicago Midway

Tue 3/17

10:45 am-10:30 pm

1 stop11h 45m

$587

PeoriaChicago

PIA - MDW

PIAMDW

Greater Peoria

Wed 2/18

12:41 pm-9:28 am

1 stop20h 47m

Chicago Midway

Sun 2/22

3:21 pm-7:51 pm

2 stops28h 30m

$620

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Wed 3/11

11:28 am-8:34 am

1 stop21h 06m

Chicago Midway

Tue 3/17

1:04 pm-4:33 pm

1 stop27h 29m

$691

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Wed 3/11

11:28 am-8:34 am

1 stop21h 06m

Chicago Midway

Sun 3/15

9:24 am-9:08 am

1 stop23h 44m

$718

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 3/7

6:00 am-10:21 am

1 stop4h 21m

Chicago Midway

Sun 3/8

9:35 am-5:18 pm

2 stops7h 43m

$1,368

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, Allegiant Air, and Delta 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

Tue, Wed, Thu, Fri, Sat and Sun
The fastest flight from Illinois to Chicago Midway Airport takes 1h 05m
Direct flights go from Illinois to Chicago Midway Airport on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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  • 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
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 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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