$243 Cheap Flights from Evansville (EVV) to Chicago (MDW)

View $243 flight on Thu, Jan 1, 2026Opens in a new window

Popular airlines from Evansville, IN (EVV-Evansville Regional) to Chicago Midway Airport (MDW)

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Cheap Flights from Evansville to Chicago (EVV-MDW)

Prices were available within the past 7 days and start at $243 for one-way flights and $374 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Feb 10 - Tue, Feb 24
EVV
Evansville
MDW
Chicago
$374 Roundtrip, found 5 days ago
$374
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 10 from Evansville to Chicago, returning Tue, Feb 24, priced at $374 found 5 days ago
Delta
Tue, Feb 3 - Sat, Feb 21
EVV
Evansville
MDW
Chicago
$384 Roundtrip, found 5 days ago
$384
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 3 from Evansville to Chicago, returning Sat, Feb 21, priced at $384 found 5 days ago
Delta
Tue, Dec 9 - Tue, Dec 16
EVV
Evansville
MDW
Chicago
$394 Roundtrip, found 1 day ago
$394
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Dec 9 from Evansville to Chicago, returning Tue, Dec 16, priced at $394 found 1 day ago
Delta
Sat, Feb 14 - Tue, Feb 24
EVV
Evansville
MDW
Chicago
$404 Roundtrip, found 5 days ago
$404
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Feb 14 from Evansville to Chicago, returning Tue, Feb 24, priced at $404 found 5 days ago
Delta
Tue, Feb 3 - Wed, Feb 18
EVV
Evansville
MDW
Chicago
$405 Roundtrip, found 5 days ago
$405
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 3 from Evansville to Chicago, returning Wed, Feb 18, priced at $405 found 5 days ago
Delta
Sat, Dec 6 - Tue, Dec 16
EVV
Evansville
MDW
Chicago
$411 Roundtrip, found 5 days ago
$411
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Dec 6 from Evansville to Chicago, returning Tue, Dec 16, priced at $411 found 5 days ago
Delta
Mon, Feb 2 - Sat, Feb 21
EVV
Evansville
MDW
Chicago
$414 Roundtrip, found 5 days ago
$414
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Feb 2 from Evansville to Chicago, returning Sat, Feb 21, priced at $414 found 5 days ago
Delta
Thu, Jan 1 - Tue, Jan 20
EVV
Evansville
MDW
Chicago
$419 Roundtrip, found 5 days ago
$419
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Jan 1 from Evansville to Chicago, returning Tue, Jan 20, priced at $419 found 5 days ago
Delta
Sat, Dec 13 - Tue, Dec 16
EVV
Evansville
MDW
Chicago
$421 Roundtrip, found 1 day ago
$421
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 13 from Evansville to Chicago, returning Tue, Dec 16, priced at $421 found 1 day ago
Delta
Mon, Jan 19 - Mon, Feb 2
EVV
Evansville
MDW
Chicago
$424 Roundtrip, found 5 days ago
$424
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Jan 19 from Evansville to Chicago, returning Mon, Feb 2, priced at $424 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $439
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $439
Flights from Evansville (EVV) to Chicago (MDW)
Origin airport
Evansville Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$373
Distance
258 mi

Evansville to Chicago Flights

The cheapest times to fly from Evansville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Evansville to Chicago are during the month of February. You can find some of the cheapest flights from Evansville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Evansville to Chicago

Sunday is one of the best days to book for cheap flights from Evansville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Evansville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Evansville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $243 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Evansville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Evansville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $243 or cheap return flight from $374 from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW)?
February is the cheapest month to fly from EVV to MDW. Traveling outside of peak seasons is often the key to finding a great deal.
What is the cheapest airline that flies from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from EVV to MDW. Then, sort your results by "Price (lowest to highest)" to pick up a good deal.
How many flights per day from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights available from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from EVV to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW)?
Opt for a flight from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Evansville Regional Airport (EVV)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Evansville Regional Airport (EVV). Compare the available options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a flight from EVV to MDW generally means paying more. While it's possible to find some last-minute offers, there's no guarantee. Allow some flexibility in your schedule for the best chance of snagging a bargain.
Is it cheaper to book an EVV to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking an EVV to MDW flight and hotel package with Expedia could result in significant savings. Better yet, having it all in one place takes the hassle out of planning your trip. Just secure your flights and select from our extensive range of hotels, then personalize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Evansville Regional Airport (EVV) to Midway Intl. Airport (MDW)?
If you booked your EVV to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

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*Available to One Key members.