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$375+ Cheap flights from Evansville (EVV) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — MDW
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/167:46 pm
EVV
-
MDW
2 stops23h 21m
Multiple Airlines
Fri 2/207:30 am
MDW
-
EVV
1 stop11h 36m
Multiple Airlines
Deal found 1/31$375
This Delta deal was found by Cheapflights users on 2/2. 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 3/76:00 am
EVV
-
MDW
1 stop4h 21m
Delta
Sun 3/89:35 am
MDW
-
EVV
2 stops7h 43m
Delta
Deal found 2/2$1,368
This Delta deal was found by Cheapflights users on 2/1. 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 4/36:00 am
EVV
-
MDW
2 stops6h 29m
Delta
Sun 4/51:10 pm
MDW
-
EVV
2 stops9h 13m
Delta
Deal found 2/1$1,396
This Delta deal was found by Cheapflights users on 2/3. 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.
Sun 2/156:00 am
EVV
-
MDW
1 stop4h 06m
Delta
Thu 2/196:00 am
MDW
-
EVV
1 stop4h 33m
Delta
Deal found 2/3$1,401
This Delta deal was found by Cheapflights users on 2/2. 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.
Mon 4/66:00 am
EVV
-
MDW
2 stops6h 29m
Delta
Mon 4/139:27 am
MDW
-
EVV
2 stops7h 51m
Delta
Deal found 2/2$1,404

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$375
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$461
Provider with most accurate pricing for Evansville Dress Regional-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Evansville Dress Regional-Chicago Midway flights.
Search Deals
From Evansville Dress Regional to Chicago Midway
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 3, 2026.
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

Mon 2/16

7:46 pm-7:07 pm

2 stops23h 21m

Chicago Midway

Fri 2/20

7:30 am-7:06 pm

1 stop11h 36m

$375

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 4/3

6:00 am-12:29 pm

2 stops6h 29m

Chicago Midway

Sun 4/5

1:10 pm-10:23 pm

2 stops9h 13m

$1,396

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 4/6

6:00 am-12:02 pm

1 stop6h 02m

Chicago Midway

Mon 4/13

1:23 pm-10:40 pm

2 stops9h 17m

$1,398

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 2/15

6:00 am-10:06 am

1 stop4h 06m

Chicago Midway

Thu 2/19

6:00 am-10:33 am

1 stop4h 33m

$1,401

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 2/16

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Fri 2/20

12:45 pm-5:14 pm

1 stop4h 29m

$1,401

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 3/7

6:00 am-10:21 am

1 stop4h 21m

Chicago Midway

Sun 3/8

12:47 pm-5:18 pm

1 stop4h 31m

$1,431

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 2/12

11:14 am-5:45 pm

1 stop6h 31m

$701

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Compare providers for flights from Evansville to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Evansville to Midway in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Evansville-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Evansville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Evansville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Evansville-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Evansville-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, September is the cheapest month in which you can book a flight from Evansville to Chicago Midway Airport (average of $77). Flying from Evansville to Chicago Midway Airport in February is currently the most expensive (average of $338). 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.

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

    There are many flights that can get you from Evansville to Chicago Midway Airport in 6h 29m. Fly via Delta to get the fastest option. The distance from Evansville to Chicago Midway Airport is about 259 mi.

  • 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, September is the cheapest month in which you can book a flight from Evansville to Chicago Midway Airport (average of $77). Flying from Evansville to Chicago Midway Airport in February is currently the most expensive (average of $338). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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