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Cheap flights from Evansville to Chicago from $112

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Evansville to Chicago departing on 12/15. 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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Find the cheapest flights from Evansville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:59 pm - 8:52 amEVV-MDW
14h 53m2 stops
Delta Logo
6:35 pm - 10:22 pmMDW-EVV
27h 47m2 stops
$394Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Delta Logo
5:59 pm - 3:38 pmEVV-MDW
21h 39m1 stop
Delta Logo
1:49 pm - 10:55 amMDW-EVV
21h 06m2 stops
$397Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Delta Logo
5:59 pm - 9:53 amEVV-MDW
15h 54m1 stop
Delta Logo
12:48 pm - 10:22 pmMDW-EVV
9h 34m1 stop
$439Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
12:22 pm - 9:58 pmEVV-MDW
9h 36m1 stop
Multiple Airlines Logo
2:16 pm - 11:42 amMDW-EVV
21h 26m1 stop
$444Multiple Airlines
Find Deal
Fri, Dec 19 - Sun, Dec 21
Multiple Airlines Logo
12:22 pm - 10:12 pmEVV-MDW
9h 50m2 stops
Multiple Airlines Logo
2:16 pm - 11:42 amMDW-EVV
21h 26m1 stop
$493Multiple Airlines
Find Deal
Fri, Dec 19 - Sun, Dec 21
Delta Logo
5:59 pm - 12:46 pmEVV-MDW
18h 47m2 stops
Delta Logo
6:35 pm - 10:55 amMDW-EVV
16h 20m2 stops
$560Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Delta Logo
5:59 pm - 3:38 pmEVV-MDW
21h 39m1 stop
Delta Logo
1:49 pm - 10:55 amMDW-EVV
21h 06m2 stops
$582Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Delta Logo
5:59 pm - 3:38 pmEVV-MDW
21h 39m1 stop
Delta Logo
6:00 am - 5:19 pmMDW-EVV
11h 19m1 stop
$593Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Delta Logo
10:09 am - 6:06 pmEVV-MDW
7h 57m2 stops
Delta Logo
1:14 pm - 9:47 pmMDW-EVV
8h 33m2 stops
$1,276Delta
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Sat, Dec 13 - Wed, Dec 17
Delta Logo
5:55 pm - 11:47 pmEVV-MDW
5h 52m1 stop
Delta Logo
9:34 am - 5:11 pmMDW-EVV
7h 37m2 stops
$1,338Delta
Find Deal
Sat, Dec 13 - Wed, Dec 17

Delta flights from Evansville to Chicago Midway Airport

Our best Delta deals on Evansville to Chicago Midway Airport flight tickets
Delta
Jan 23
EVV5:59 pmEvansville Dress Regional
14h 53m
2 stops
MDW8:52 amChicago Midway
Jan 26
MDW6:35 pmChicago Midway
27h 47m
2 stops
EVV10:22 pmEvansville Dress Regional
$394
Find similar
Delta
Jan 23
EVV5:59 pmEvansville Dress Regional
21h 39m
1 stop
MDW3:38 pmChicago Midway
Jan 26
MDW1:49 pmChicago Midway
21h 06m
2 stops
EVV10:55 amEvansville Dress Regional
$397
Find similar
Delta
Jan 23
EVV5:59 pmEvansville Dress Regional
15h 54m
1 stop
MDW9:53 amChicago Midway
Jan 26
MDW12:48 pmChicago Midway
9h 34m
1 stop
EVV10:22 pmEvansville Dress Regional
$439
Find similar

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 December 2, 2025.
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

Fri 1/23

5:59 pm-8:52 am

2 stops14h 53m

Chicago Midway

Mon 1/26

6:35 pm-10:22 pm

2 stops27h 47m

$394

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 1/23

5:59 pm-3:38 pm

1 stop21h 39m

Chicago Midway

Mon 1/26

1:49 pm-10:55 am

2 stops21h 06m

$397

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 1/23

5:59 pm-9:53 am

1 stop15h 54m

Chicago Midway

Mon 1/26

12:48 pm-10:22 pm

1 stop9h 34m

$439

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 12/19

12:22 pm-9:58 pm

1 stop9h 36m

Chicago Midway

Sun 12/21

2:16 pm-11:42 am

1 stop21h 26m

$444

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 12/19

12:22 pm-10:12 pm

2 stops9h 50m

Chicago Midway

Sun 12/21

2:16 pm-11:42 am

1 stop21h 26m

$493

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 1/23

5:59 pm-12:46 pm

2 stops18h 47m

Chicago Midway

Mon 1/26

6:35 pm-10:55 am

2 stops16h 20m

$560

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 1/23

5:59 pm-3:38 pm

1 stop21h 39m

Chicago Midway

Mon 1/26

1:49 pm-10:55 am

2 stops21h 06m

$582

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 1/23

5:59 pm-3:38 pm

1 stop21h 39m

Chicago Midway

Mon 1/26

6:00 am-5:19 pm

1 stop11h 19m

$593

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 12/13

10:09 am-6:06 pm

2 stops7h 57m

Chicago Midway

Wed 12/17

1:14 pm-9:47 pm

2 stops8h 33m

$1,276

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 12/13

5:55 pm-11:47 pm

1 stop5h 52m

Chicago Midway

Wed 12/17

9:34 am-5:11 pm

2 stops7h 37m

$1,338

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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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

5h 52m

Direct flights

None
The fastest flight from Evansville to Chicago Midway Airport takes 5h 52m
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 5h 22m.

  • 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.

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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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