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$46+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$91
(Southwest)

One-way from

$46
(Southwest)

Popular in

July

Cheapest in

January

Average price

$302
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. 5% potential increase in price ($13 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 July 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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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 8/267:10 amSTL - MDW
Nonstop1h 10mSouthwest
Wed 8/2711:25 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 7/29$91
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:55 pmSTL - MDW
1 stop5h 15mDelta
Tue 9/161:08 pmMDW - STL
1 stop3h 29mDelta
Deal found 7/28$177
This Priceline deal was found by Cheapflights users on 7/29. 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.
Sat 8/162:52 pmSTL - MDW
1 stop7h 41mFrontier
Sat 8/236:10 amMDW - STL
1 stop7h 23mFrontier
Deal found 7/29$179
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amEVV - MDW
2 stops6h 28mDelta
Sun 11/21:08 pmMDW - EVV
2 stops8h 45mDelta
Deal found 7/31$1,114

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 July 31, 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

Tue 8/26

7:10 am-8:20 am

Nonstop1h 10m

Chicago Midway

Wed 8/27

11:25 am-12:35 pm

Nonstop1h 10m

$91

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

3:55 pm-9:10 pm

1 stop5h 15m

Chicago Midway

Tue 9/16

1:08 pm-4:37 pm

1 stop3h 29m

$177

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/16

2:52 pm-10:33 pm

1 stop7h 41m

Chicago Midway

Sat 8/23

6:10 am-1:33 pm

1 stop7h 23m

$179

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 10/31

6:00 am-12:28 pm

2 stops6h 28m

Chicago Midway

Sun 11/2

1:08 pm-9:53 pm

2 stops8h 45m

$1,114

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 9/16

8:40 am-9:50 am

Nonstop1h 10m

$46

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/30

3:36 pm-9:12 pm

1 stop5h 36m

$89

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 11/1

5:48 pm-1:44 pm

1 stop19h 56m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/25

12:05 pm-8:52 pm

3 stops32h 47m

$173

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 8/14

10:13 am-6:37 pm

2 stops8h 24m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier from Illinois to Chicago Midway Airport by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines to fly from Illinois to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $46 on Southwest. Other airlines that offer cheap prices include Delta from $89 and Frontier from $97 one-way.

  • 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
Valparaiso
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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