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Cheap flights from Evansville to Chicago from $325

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Evansville to Chicago departing on 2/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:46 pm - 7:07 pm
EVV
-
MDW
23h 21m
2 stops
Multiple Airlines Logo
7:30 am - 7:06 pm
MDW
-
EVV
11h 36m
1 stop
$325Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
7:46 pm - 2:55 pm
EVV
-
MDW
19h 09m
1 stop
Multiple Airlines Logo
3:00 pm - 7:06 pm
MDW
-
EVV
28h 06m
2 stops
$356Multiple Airlines
Fri, Feb 20 - Sun, Feb 22
Delta Logo
5:59 pm - 10:31 pm
EVV
-
MDW
4h 32m
1 stop
Delta Logo
10:49 am - 5:14 pm
MDW
-
EVV
6h 25m
1 stop
$1,401Delta
Thu, Feb 19 - Sun, Feb 22
Delta Logo
11:14 am - 5:45 pm
EVV
-
MDW
6h 31m
1 stop
Delta Logo
1:28 pm - 10:20 pm
MDW
-
EVV
8h 52m
2 stops
$1,406Delta
Thu, Feb 19 - Sat, Feb 21
Delta Logo
6:00 am - 11:56 am
EVV
-
MDW
5h 56m
1 stop
Delta Logo
6:00 am - 12:53 pm
MDW
-
EVV
6h 53m
1 stop
$1,481Delta
Fri, Jul 17 - Sun, Jul 19
Delta Logo
6:00 am - 11:56 am
EVV
-
MDW
5h 56m
1 stop
Delta Logo
9:30 am - 4:56 pm
MDW
-
EVV
7h 26m
2 stops
$1,486Delta
Fri, Jul 17 - Sun, Jul 19
Delta Logo
10:05 am - 6:31 pm
EVV
-
MDW
8h 26m
2 stops
Delta Logo
9:30 am - 4:56 pm
MDW
-
EVV
7h 26m
2 stops
$1,805Delta
Fri, Jul 17 - Sun, Jul 19

Delta flights from Evansville to Chicago Midway Airport

Our best Delta deals on Evansville to Chicago Midway Airport flight tickets
Delta
Feb 19
EVV5:59 pmEvansville Dress Regional
4h 32m
1 stop
MDW10:31 pmChicago Midway
Feb 21
MDW6:00 amChicago Midway
5h 36m
1 stop
EVV11:36 amEvansville Dress Regional
$1,401
Delta
Feb 19
EVV11:14 amEvansville Dress Regional
6h 31m
1 stop
MDW5:45 pmChicago Midway
Feb 21
MDW1:28 pmChicago Midway
8h 52m
2 stops
EVV10:20 pmEvansville Dress Regional
$1,406
Delta
Jul 17
EVV6:00 amEvansville Dress Regional
5h 56m
1 stop
MDW11:56 amChicago Midway
Jul 19
MDW6:00 amChicago Midway
6h 53m
1 stop
EVV12:53 pmEvansville Dress Regional
$1,481

momondo Fare Finder

 
Customize your flight search to find flights from Evansville to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 8, 2026.
Use the filters below to find and compare flights from Evansville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 2/23

7:46 pm-7:07 pm

2 stops23h 21m

Chicago Midway

Fri 2/27

7:30 am-7:06 pm

1 stop11h 36m

$325

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 2/20

7:46 pm-2:55 pm

1 stop19h 09m

Chicago Midway

Sun 2/22

3:00 pm-7:06 pm

2 stops28h 06m

$356

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 2/19

5:59 pm-10:31 pm

1 stop4h 32m

Chicago Midway

Sun 2/22

10:49 am-5:14 pm

1 stop6h 25m

$1,401

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 2/19

11:14 am-5:45 pm

1 stop6h 31m

Chicago Midway

Sat 2/21

1:28 pm-10:20 pm

2 stops8h 52m

$1,406

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/17

6:00 am-11:56 am

1 stop5h 56m

Chicago Midway

Sun 7/19

6:00 am-12:53 pm

1 stop6h 53m

$1,481

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/17

6:00 am-11:56 am

1 stop5h 56m

Chicago Midway

Sun 7/19

9:30 am-4:56 pm

2 stops7h 26m

$1,486

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/17

10:05 am-6:31 pm

2 stops8h 26m

Chicago Midway

Sun 7/19

9:30 am-4:56 pm

2 stops7h 26m

$1,805

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Wed 2/11

11:40 am-5:29 pm

1 stop5h 49m

$701

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Evansville to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Evansville Dress Regional to Chicago Midway?

Delta is the most popular carrier operating from Evansville Dress Regional to Chicago Midway

When to book flights from Evansville to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Evansville to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Evansville to Chicago Midway Airport (EVV to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Evansville to Chicago Midway Airport

Fastest flight time

4h 32m

Direct flights

None
The fastest flight from Evansville to Chicago Midway Airport takes 4h 32m
There are no direct flights from Evansville to Chicago Midway Airport. There are no popular flight routes from Evansville to Chicago Midway Airport.
Search flight deals

  • How far is Evansville Dress Regional to Chicago Midway by plane?

    The distance between Evansville Dress Regional and Chicago Midway is about 263.4 mi. In terms of flight time, this usually takes a little over 4h 32m.

  • When did momondo last update prices for flights from Evansville Dress Regional Airport to Chicago Midway Airport?

    Prices for flights from Evansville Dress Regional Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Evansville Dress Regional Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Evansville Dress Regional Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

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Why use momondo?

Why should I use momondo to find a flight deal from Evansville to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Evansville to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Evansville to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Evansville to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Evansville to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Evansville to Chicago.

I’m not ready to book a flight from Evansville to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Evansville to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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