HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$172+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — MDW
Aug 24 — Aug 311
Sun 8/24
Sun 8/31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Evansville to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 19, 2025.

Round-trip from

$1,123
(Delta)

One-way from

$172
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$397
From Evansville Dress Regional to Chicago Midway
Search Deals
One-way flight from Evansville Dress Regional to Chicago Midway
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($108 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 August 2025
Search Deals

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 August 19, 2025.

This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:23 amEVV - MDW
1 stop5h 25mDelta
Sat 9/276:00 amMDW - EVV
1 stop6h 40mDelta
Deal found 8/17$1,123
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1910:14 amEVV - MDW
2 stops8h 21mDelta
Sun 9/211:08 pmMDW - EVV
2 stops8h 41mDelta
Deal found 8/17$1,134
This Delta deal was found by Cheapflights users on 8/18. 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 8/3010:13 amEVV - MDW
2 stops8h 24mDelta
Mon 9/19:30 amMDW - EVV
2 stops6h 50mDelta
Deal found 8/18$1,139
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1910:13 amEVV - MDW
2 stops8h 24mDelta
Wed 8/209:31 amMDW - EVV
2 stops7h 39mDelta
Deal found 8/17$1,146
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/16:10 amEVV - MDW
2 stops6h 18mDelta
Fri 9/54:25 pmMDW - EVV
1 stop5h 29mDelta
Deal found 8/17$1,228
This Delta deal was found by Cheapflights users on 8/18. 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 8/3110:13 amEVV - MDW
2 stops8h 24mDelta
Thu 9/44:25 pmMDW - EVV
1 stop5h 29mDelta
Deal found 8/18$1,233
This Delta deal was found by Cheapflights users on 8/18. 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 9/55:00 pmEVV - MDW
1 stop4h 26mDelta
Sun 9/74:25 pmMDW - EVV
1 stop5h 29mDelta
Deal found 8/18$1,323

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 August 19, 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

Fri 9/26

1:17 pm-5:51 pm

1 stop4h 34m

Chicago Midway

Tue 9/30

10:35 am-5:21 pm

1 stop6h 46m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 10/14

6:02 pm-10:14 pm

1 stop4h 12m

Chicago Midway

Tue 10/21

6:00 am-12:43 pm

1 stop6h 43m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 9/19

6:23 am-11:48 am

1 stop5h 25m

Chicago Midway

Sat 9/27

6:00 am-12:40 pm

1 stop6h 40m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 9/8

5:00 pm-9:26 pm

1 stop4h 26m

Chicago Midway

Thu 9/11

12:43 pm-5:21 pm

1 stop4h 38m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 9/19

6:23 am-11:48 am

1 stop5h 25m

Chicago Midway

Sun 9/21

6:00 am-12:37 pm

1 stop6h 37m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 9/15

1:17 pm-5:35 pm

1 stop4h 18m

Chicago Midway

Thu 9/18

6:00 am-12:37 pm

1 stop6h 37m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 10/4

2:00 pm-9:10 pm

1 stop7h 10m

Chicago Midway

Sun 10/5

6:00 am-12:37 pm

1 stop6h 37m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 10/31

6:02 am-12:28 pm

2 stops6h 26m

Chicago Midway

Sun 11/2

5:04 pm-9:53 pm

1 stop4h 49m

$1,128

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 10/19

8:17 pm-4:33 pm

2 stops20h 16m

$172

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 9/11

10:53 am-4:43 pm

2 stops29h 50m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 16 results
1
2

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.

  • 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 4h 34m. 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, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.