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$186+ Cheap flights from Evansville (EVV) 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — MDW
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Evansville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Evansville (EVV) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 17, 2025.

Round-trip from

$275
(Kiwi.com)

One-way from

$186
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$358
From Evansville Dress Regional to Chicago Midway
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One-way flight from Evansville Dress Regional to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($18 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 Evansville to Midway

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

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.
dom. 11/1612:53 pmEVV - MDW
1 stop11h 37mMultiple Airlines
jue. 11/204:00 pmMDW - EVV
2 stops22h 12mMultiple Airlines
Deal found 9/15$275
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.
dom. 11/1612:53 pmEVV - MDW
1 stop11h 37mMultiple Airlines
lun. 11/179:27 amMDW - EVV
1 stop7h 28mMultiple Airlines
Deal found 9/15$321
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.
vie. 11/145:35 pmEVV - MDW
1 stop16h 51mMultiple Airlines
jue. 11/204:00 pmMDW - EVV
2 stops22h 12mMultiple Airlines
Deal found 9/15$328
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.
vie. 11/145:35 pmEVV - MDW
1 stop16h 51mMultiple Airlines
lun. 11/179:27 amMDW - EVV
1 stop7h 28mMultiple Airlines
Deal found 9/15$369
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.
vie. 9/1912:22 pmEVV - MDW
1 stop21h 29mMultiple Airlines
dom. 9/2110:13 amMDW - EVV
1 stop25h 29mMultiple Airlines
Deal found 9/16$393
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.
jue. 11/138:19 amEVV - MDW
2 stops15h 36mMultiple Airlines
lun. 11/179:27 amMDW - EVV
1 stop7h 28mMultiple Airlines
Deal found 9/15$404

Cheapflights Fare Finder

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

Fly from

Evansville

Fly to

Midway

Route

Depart

Return

Price

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

dom. 11/16

12:53 pm-12:30 am

1 stop11h 37m

Chicago Midway

lun. 11/17

9:27 am-4:55 pm

1 stop7h 28m

$321

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

vie. 11/14

5:35 pm-10:26 am

1 stop16h 51m

Chicago Midway

lun. 11/17

9:27 am-4:55 pm

1 stop7h 28m

$369

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

jue. 11/13

8:19 am-11:55 pm

2 stops15h 36m

Chicago Midway

lun. 11/17

9:27 am-4:55 pm

1 stop7h 28m

$404

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

sáb. 11/15

10:10 am-11:32 pm

1 stop13h 22m

Chicago Midway

lun. 11/17

10:47 am-10:08 pm

1 stop11h 21m

$485

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

sáb. 11/15

6:00 am-11:32 pm

1 stop17h 32m

Chicago Midway

mar. 11/18

6:00 am-10:08 pm

1 stop16h 08m

$485

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

lun. 10/13

5:35 pm-11:25 pm

2 stops29h 50m

$186

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

mar. 11/25

12:14 pm-1:21 pm

2 stops25h 07m

$341

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

lun. 10/13

10:20 am-4:09 pm

1 stop5h 49m

$741

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Best time to book a flight from Evansville to Midway

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

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

Currently, April is the cheapest month in which you can book a flight from Evansville to Chicago Midway Airport (average of $160). Flying from Evansville 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.

Related info for your journey

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

  • What airport do you fly from for flights from Evansville to Chicago Midway?

    For a flight from Evansville to Chicago Midway, you will be flying from Dress Regional. Evansville Dress Regional (EVV) is just 4.4 mi from the center of the city. Dress Regional is the only Evansville airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Evansville Dress Regional on a regular basis.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Evansville to Chicago Midway Airport (average of $160). Flying from Evansville 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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