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

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Midway to Illinois

Keep the following information in mind while searching for Midway to Illinois flight deals. Data was last updated September 17, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)
From Chicago Midway to Illinois
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One-way flight from Chicago Midway to Illinois
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Find flight deals from Midway to Illinois

Cheapest flights from Midway to Illinois
Explore the most affordable flight options available from Midway to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

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.
Wed 10/1512:40 pmMDW - STL
Nonstop1h 10mSouthwest
Wed 10/221:15 pmSTL - MDW
Nonstop1h 10mSouthwest
Deal found 9/15$97
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.
Mon 10/206:00 pmMDW - STL
1 stop3h 30mSouthwest
Wed 10/221:15 pmSTL - MDW
Nonstop1h 10mSouthwest
Deal found 9/15$107
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.
Sat 10/188:20 amMDW - STL
2 stops6h 10mSouthwest
Thu 10/235:40 amSTL - MDW
Nonstop1h 10mSouthwest
Deal found 9/16$112
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 10/712:40 pmMDW - STL
Nonstop1h 10mSouthwest
Wed 10/221:15 pmSTL - MDW
Nonstop1h 10mSouthwest
Deal found 9/16$134
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:20 amMDW - STL
1 stop8h 44mFrontier
Thu 10/24:00 pmSTL - MDW
1 stop7h 41mFrontier
Deal found 9/15$143
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.
Tue 10/78:40 pmMDW - STL
Nonstop1h 10mSouthwest
Fri 10/107:45 pmSTL - MDW
1 stop4h 10mSouthwest
Deal found 9/15$144
This Priceline deal was found by Cheapflights users on 9/14. 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.
Sun 9/216:20 amMDW - STL
1 stop8h 44mFrontier
Mon 9/224:00 pmSTL - MDW
1 stop7h 20mFrontier
Deal found 9/14$150
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:48 pmMDW - STL
1 stop16h 18mFrontier
Sun 10/51:57 pmSTL - MDW
1 stop17h 26mFrontier
Deal found 9/16$156
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.
Mon 11/36:20 amMDW - STL
Nonstop1h 15mSouthwest
Mon 11/37:20 pmSTL - MDW
Nonstop1h 10mSouthwest
Deal found 9/16$157
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/254:56 pmMDW - PIA
2 stops38h 38mMultiple Airlines
Thu 10/210:42 amPIA - MDW
1 stop26h 02mMultiple Airlines
Deal found 9/15$550

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Illinois 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 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Illinois that are best for you.

Fly from

Midway

Fly to

Illinois

Route

Depart

Return

Price

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Tue 10/14

8:40 pm-9:50 pm

Nonstop1h 10m

Lambert-St Louis

Tue 10/21

1:15 pm-2:25 pm

Nonstop1h 10m

$97

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Tue 10/28

7:55 am-9:10 am

Nonstop1h 15m

Lambert-St Louis

Thu 10/30

6:30 pm-7:40 pm

Nonstop1h 10m

$97

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Wed 10/15

5:30 am-10:15 am

1 stop4h 45m

Lambert-St Louis

Wed 10/15

5:05 pm-6:10 pm

Nonstop1h 05m

$107

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Tue 10/7

10:05 am-3:00 pm

1 stop4h 55m

Lambert-St Louis

Wed 10/22

5:05 pm-6:10 pm

Nonstop1h 05m

$107

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Mon 11/3

10:05 am-4:05 pm

1 stop6h 00m

Lambert-St Louis

Mon 11/3

7:20 pm-8:30 pm

Nonstop1h 10m

$107

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Sat 10/18

8:15 am-2:40 pm

1 stop6h 25m

Lambert-St Louis

Thu 10/23

5:40 am-6:50 am

Nonstop1h 10m

$107

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Mon 10/20

6:00 pm-9:30 pm

1 stop3h 30m

Lambert-St Louis

Wed 10/22

5:05 pm-6:10 pm

Nonstop1h 05m

$107

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Wed 11/5

3:45 pm-7:25 pm

1 stop3h 40m

Lambert-St Louis

Sat 11/8

5:45 pm-6:55 pm

Nonstop1h 10m

$107

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Sat 10/25

6:30 am-7:40 am

Nonstop1h 10m

Lambert-St Louis

Sat 10/25

1:45 pm-8:20 pm

2 stops6h 35m

$112

ChicagoSt. Louis

MDW - STL

MDWSTL

Chicago Midway

Thu 11/13

6:45 am-8:00 am

Nonstop1h 15m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 21 results
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Best time to book a flight from Midway to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Midway 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 Chicago Midway Airport to Illinois
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 Midway to Illinois. 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 Chicago Midway Airport to Illinois?

    For as low as $97, Southwest can have you in Illinois from Chicago Midway Airport in 1h 10m. There are 251 mi between Chicago Midway Airport and Illinois. All flights are typically nonstop.

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

    Most travelers choose Chicago Midway - Lambert-St Louis, Chicago Midway - Bloomington-Normal or Chicago Midway - Greater Peoria when deciding on the best route from Chicago Midway Airport to Illinois.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Illinois 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 Chicago Midway Airport to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Illinois (average of $245). Flying from Chicago Midway Airport to Illinois in March is currently the most expensive (average of $321). 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

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Alternative routes for Midway to Illinois

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