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$316+ 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 6/22. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$341
(Mytrip)

One-way from

$316
(Mytrip)

Popular in

October

Cheapest in

May
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. 18% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/262:04 pmEVV - MDW
2 stops23h 59mAllegiant Air
Mon 6/309:12 amMDW - EVV
1 stop6h 37mAllegiant Air
Deal found 6/11$341
This Delta deal was found by Cheapflights users on 6/12. 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 6/2710:23 amEVV - MDW
2 stops8h 18mDelta
Tue 7/11:09 pmMDW - EVV
2 stops8h 47mDelta
Deal found 6/12$1,214

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 June 12, 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

Thu 6/26

2:04 pm-2:03 pm

2 stops23h 59m

Chicago Midway

Mon 6/30

9:12 am-3:49 pm

1 stop6h 37m

$341

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 6/27

10:23 am-6:41 pm

2 stops8h 18m

Chicago Midway

Tue 7/1

1:09 pm-9:56 pm

2 stops8h 47m

$1,214

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 6/22

2:04 pm-2:03 pm

2 stops23h 59m

$316

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 6/22

1:25 pm-6:02 pm

1 stop4h 37m

$741

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.3
Good
725 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 Evansville?

Book flights to Evansville if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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