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Cheap flights from Illinois to Chicago from $50

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 9/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
3:00 pm - 4:10 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
8:15 am - 9:35 amMDW  Chicago Midway-STL Lambert-St Louis
1h 20mnonstop
$117Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
5:50 am - 6:55 amSTL  Lambert-St Louis-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
10:05 pm - 11:15 pmMDW  Chicago Midway-STL Lambert-St Louis
1h 10mnonstop
$117Southwest
Wed, Oct 14 - Thu, Oct 15
Southwest Logo
8:50 pm - 10:00 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
4:40 pm - 5:55 pmMDW  Chicago Midway-STL Lambert-St Louis
1h 15mnonstop
$117Southwest
Mon, Sep 14 - Tue, Sep 15
Southwest Logo
5:45 am - 6:55 amSTL  Lambert-St Louis-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
8:45 pm - 9:55 pmMDW  Chicago Midway-STL Lambert-St Louis
1h 10mnonstop
$117Southwest
Sat, Nov 14 - Mon, Nov 16
Southwest Logo
6:15 pm - 7:20 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
10:05 pm - 11:15 pmMDW  Chicago Midway-STL Lambert-St Louis
1h 10mnonstop
$117Southwest
Mon, Sep 28 - Mon, Oct 5
Southwest Logo
2:20 pm - 3:30 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
7:55 am - 9:15 amMDW  Chicago Midway-STL Lambert-St Louis
1h 20mnonstop
$117Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
12:50 pm - 1:55 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
4:40 pm - 5:55 pmMDW  Chicago Midway-STL Lambert-St Louis
1h 15mnonstop
$117Southwest
Wed, Sep 9 - Wed, Sep 9
Southwest Logo
8:50 pm - 10:00 pmSTL  Lambert-St Louis-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
9:20 am - 10:30 amMDW  Chicago Midway-STL Lambert-St Louis
1h 10mnonstop
$117Southwest
Thu, Sep 17 - Thu, Sep 24
Frontier Logo
2:29 pm - 11:44 pmSTL  Lambert-St Louis-MDW Chicago Midway
9h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 1:10 pmMDW  Chicago Midway-STL Lambert-St Louis
6h 45m1 stop Atlanta Hartsfield-Jackson
$119Frontier
Mon, Sep 28 - Mon, Oct 5
Frontier Logo
2:29 pm - 11:44 pmSTL  Lambert-St Louis-MDW Chicago Midway
9h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 1:10 pmMDW  Chicago Midway-STL Lambert-St Louis
6h 45m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Fri, Sep 11 - Fri, Sep 18

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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
Sep 17
STL8:50 pmLambert-St Louis
1h 10m
MDW10:00 pmChicago Midway
Sep 24
MDW9:20 amChicago Midway
1h 10m
STL10:30 amLambert-St Louis
$117
Southwest
Sep 5
STL5:45 amLambert-St Louis
1h 05m
MDW6:50 amChicago Midway
Sep 6
MDW8:10 amChicago Midway
5h 35m
1 stop
STL1:45 pmLambert-St Louis
$127
Southwest
Sep 5
STL2:05 pmLambert-St Louis
5h 10m
1 stop
MDW7:15 pmChicago Midway
Sep 6
MDW8:10 amChicago Midway
5h 35m
1 stop
STL1:45 pmLambert-St Louis
$128

Frontier flights from Illinois to Chicago Midway Airport

Our best Frontier deals on Illinois to Chicago Midway Airport flight tickets
Frontier
Sep 28
STL2:29 pmLambert-St Louis
9h 15m
1 stop
MDW11:44 pmChicago Midway
Oct 5
MDW6:25 amChicago Midway
6h 45m
1 stop
STL1:10 pmLambert-St Louis
$119
Frontier
Sep 4
STL6:17 pmLambert-St Louis
28h 30m
1 stop
MDW10:47 pmChicago Midway
Sep 9
MDW6:25 amChicago Midway
6h 45m
1 stop
STL1:10 pmLambert-St Louis
$179
Frontier
Sep 21
STL2:29 pmLambert-St Louis
9h 15m
1 stop
MDW11:44 pmChicago Midway
Sep 24
MDW6:46 pmChicago Midway
18h 24m
1 stop
STL1:10 pmLambert-St Louis
$180

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 August 16, 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 Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Sat 9/5

3:00 pm-4:10 pm

Nonstop1h 10m

Chicago Midway

Tue 9/8

8:15 am-9:35 am

Nonstop1h 20m

$117
Quickest round-trip

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Wed 10/14

5:50 am-6:55 am

Nonstop1h 05m

Chicago Midway

Thu 10/15

10:05 pm-11:15 pm

Nonstop1h 10m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Mon 9/14

8:50 pm-10:00 pm

Nonstop1h 10m

Chicago Midway

Tue 9/15

4:40 pm-5:55 pm

Nonstop1h 15m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Sat 11/14

5:45 am-6:55 am

Nonstop1h 10m

Chicago Midway

Mon 11/16

8:45 pm-9:55 pm

Nonstop1h 10m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Mon 9/28

6:15 pm-7:20 pm

Nonstop1h 05m

Chicago Midway

Mon 10/5

10:05 pm-11:15 pm

Nonstop1h 10m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Mon 9/21

2:20 pm-3:30 pm

Nonstop1h 10m

Chicago Midway

Mon 9/28

7:55 am-9:15 am

Nonstop1h 20m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Wed 9/9

12:50 pm-1:55 pm

Nonstop1h 05m

Chicago Midway

Wed 9/9

4:40 pm-5:55 pm

Nonstop1h 15m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Thu 9/17

8:50 pm-10:00 pm

Nonstop1h 10m

Chicago Midway

Thu 9/24

9:20 am-10:30 am

Nonstop1h 10m

$117

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Mon 9/28

2:29 pm-11:44 pm

1 stop9h 15m

Chicago Midway

Mon 10/5

6:25 am-1:10 pm

1 stop6h 45m

$119

St. LouisChicago

STL Lambert-St Louis - MDW Chicago Midway

STLMDW

Lambert-St Louis

Fri 9/11

2:29 pm-11:44 pm

1 stop9h 15m

Chicago Midway

Fri 9/18

6:25 am-1:10 pm

1 stop6h 45m

$142

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 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 00m

Direct flights

Every day
The fastest flight from Illinois to Chicago Midway Airport takes 1h 00m
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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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