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$49+ Cheap flights from Illinois to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MDW
Oct 18 — Oct 251
Sat 10/18
Sat 10/25
1 adult, Economy
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Cheap flight deals from Illinois to Midway

Keep the following information in mind while searching for Illinois to Midway flight deals. Data was last updated September 18, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

July

Cheapest in

January

Average price

$239
From Illinois to Chicago Midway
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One-way flight from Illinois to Chicago Midway
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Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Illinois to Midway

Cheapest flights from Illinois to Midway
Explore the most affordable flight options available from Illinois to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2025.

This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:40 amSTL - MDW
Nonstop1h 10mSouthwest
Mon 10/277:40 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 9/17$97
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:40 amSTL - MDW
Nonstop1h 10mSouthwest
Thu 10/237:40 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 9/16$134
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:07 amSTL - MDW
1 stop7h 32mFrontier
Fri 11/76:15 amMDW - STL
1 stop9h 46mFrontier
Deal found 9/16$143
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:32 pmSTL - MDW
1 stop12h 49mFrontier
Sun 10/56:20 amMDW - STL
1 stop8h 44mFrontier
Deal found 9/16$144
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/314:52 pmSTL - MDW
1 stop4h 53mFrontier
Fri 11/76:15 amMDW - STL
1 stop9h 46mFrontier
Deal found 9/16$145
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:40 amSTL - MDW
Nonstop1h 10mSouthwest
Sat 10/188:20 amMDW - STL
2 stops6h 10mSouthwest
Deal found 9/15$149
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:11 amSTL - MDW
1 stop5h 46mFrontier
Wed 10/292:06 pmMDW - STL
1 stop20h 06mFrontier
Deal found 9/17$152
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/72:25 pmSTL - MDW
1 stop5h 50mSouthwest
Fri 10/106:00 pmMDW - STL
1 stop3h 30mSouthwest
Deal found 9/16$154
This Booking.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:05 pmSTL - MDW
1 stop16h 16mFrontier
Fri 10/2412:11 pmMDW - STL
1 stop20h 56mFrontier
Deal found 9/17$156
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1612:53 pmEVV - MDW
1 stop11h 37mMultiple Airlines
Mon 11/179:27 amMDW - EVV
1 stop7h 28mMultiple Airlines
Deal found 9/16$321
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1612:53 pmEVV - MDW
1 stop11h 37mMultiple Airlines
Thu 11/204:00 pmMDW - EVV
2 stops22h 12mMultiple Airlines
Deal found 9/16$322
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:35 pmEVV - MDW
1 stop16h 46mMultiple Airlines
Sun 10/199:26 pmMDW - EVV
2 stops19h 29mMultiple Airlines
Deal found 9/17$354

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated September 18, 2025.
Use the filters below to find and compare flights from Illinois to Chicago Midway Airport that are best for you.

Fly from

Illinois

Fly to

Midway

Route

Depart

Return

Price

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 10/15

6:30 am-7:40 am

Nonstop1h 10m

Chicago Midway

Wed 10/22

5:45 am-6:55 am

Nonstop1h 10m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 10/23

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Mon 10/27

7:40 am-8:50 am

Nonstop1h 10m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 10/15

6:30 am-7:40 am

Nonstop1h 10m

Chicago Midway

Wed 10/15

12:40 pm-1:50 pm

Nonstop1h 10m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 11/20

7:00 am-8:10 am

Nonstop1h 10m

Chicago Midway

Thu 11/20

11:25 am-12:35 pm

Nonstop1h 10m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 11/3

4:25 pm-5:35 pm

Nonstop1h 10m

Chicago Midway

Tue 11/4

1:45 pm-5:25 pm

1 stop3h 40m

$107

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 10/20

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Mon 10/20

6:00 pm-9:30 pm

1 stop3h 30m

$107

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 11/16

12:53 pm-12:30 am

1 stop11h 37m

Chicago Midway

Mon 11/17

9:27 am-4:55 pm

1 stop7h 28m

$321

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 11/14

5:35 pm-10:26 am

1 stop16h 51m

Chicago Midway

Mon 11/17

9:27 am-4:55 pm

1 stop7h 28m

$369

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 11/13

8:19 am-11:55 pm

2 stops15h 36m

Chicago Midway

Mon 11/17

9:27 am-4:55 pm

1 stop7h 28m

$404

PeoriaChicago

PIA - MDW

PIAMDW

Greater Peoria

Thu 10/23

5:23 pm-1:55 pm

2 stops20h 32m

Chicago Midway

Sun 10/26

4:46 pm-7:30 am

1 stop14h 44m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 41 results
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Best time to book a flight from Illinois to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Chicago Midway Airport?

    Departing from Illinois to Chicago Midway Airport will take you 1h 10m. Illinois and Chicago Midway Airport are separated by a distance of 251 mi. All flights are typically nonstop.

  • What are the most popular routes from Illinois to Chicago Midway Airport?

    The most popular flight routes from Illinois to Chicago Midway Airport are Lambert-St Louis - Chicago Midway, Evansville Dress Regional - Chicago Midway and Moline Quad-City - Chicago Midway.

  • Can I find deals for flights from Illinois to Midway that include hotel bookings?

    Yes. In addition to deals on Illinois to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Midway.

  • Can I find deals for business class flights from Illinois to Midway?

    Yes. Cheapflights offers flight deals from Illinois to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Illinois to Chicago Midway Airport (average of $160). Flying from Illinois to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Illinois to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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