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Cheap flights from Evansville to Chicago from $188

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 7/3. 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.
Multiple Airlines Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Multiple Airlines Logo
6:00 am - 9:20 am
MDW
-
EVV
27h 20m
2 stops
$402Multiple Airlines
Fri, Jun 19 - Sat, Jun 27
Multiple Airlines Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Multiple Airlines Logo
8:20 pm - 3:49 pm
MDW
-
EVV
19h 29m
2 stops
$417Multiple Airlines
Fri, Jun 12 - Fri, Jun 19
Multiple Airlines Logo
3:07 pm - 8:25 pm
EVV
-
MDW
5h 18m
1 stop
Multiple Airlines Logo
6:00 am - 7:43 am
MDW
-
EVV
25h 43m
2 stops
$425Multiple Airlines
Fri, Jul 3 - Sun, Jul 5
Allegiant Air Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Allegiant Air Logo
2:46 pm - 7:50 pm
MDW
-
EVV
29h 04m
2 stops
$442Allegiant Air
Fri, Jun 12 - Sun, Jun 14
Allegiant Air Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Allegiant Air Logo
3:28 pm - 7:23 am
MDW
-
EVV
39h 55m
2 stops
$443Allegiant Air
Mon, Jun 29 - Fri, Jul 10
Multiple Airlines Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Multiple Airlines Logo
6:00 am - 3:49 pm
MDW
-
EVV
33h 49m
2 stops
$446Multiple Airlines
Mon, Jun 29 - Tue, Jul 7
Allegiant Air Logo
3:07 pm - 8:25 pm
EVV
-
MDW
5h 18m
1 stop
Allegiant Air Logo
3:28 pm - 7:23 am
MDW
-
EVV
39h 55m
2 stops
$451Allegiant Air
Fri, Jul 3 - Fri, Jul 10
Multiple Airlines Logo
3:07 pm - 8:25 pm
EVV
-
MDW
5h 18m
1 stop
Multiple Airlines Logo
6:00 am - 3:49 pm
MDW
-
EVV
33h 49m
2 stops
$454Multiple Airlines
Fri, Jul 3 - Tue, Jul 7
Allegiant Air Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Allegiant Air Logo
2:48 pm - 7:43 am
MDW
-
EVV
16h 55m
2 stops
$481Allegiant Air
Mon, Jun 29 - Sun, Jul 5
Allegiant Air Logo
3:07 pm - 8:25 pm
EVV
-
MDW
5h 18m
1 stop
Allegiant Air Logo
2:48 pm - 7:43 am
MDW
-
EVV
16h 55m
2 stops
$489Allegiant Air
Fri, Jul 3 - Sun, Jul 5

Delta flights from Evansville to Chicago Midway Airport

Our best Delta deals on Evansville to Chicago Midway Airport flight tickets
Delta
Aug 6
EVV1:49 pmEvansville Dress Regional
8h 47m
1 stop
MDW10:36 pmChicago Midway
Aug 10
MDW10:54 amChicago Midway
11h 07m
1 stop
EVV10:01 pmEvansville Dress Regional
$569
Delta
Jun 28
EVV5:58 pmEvansville Dress Regional
4h 19m
1 stop
MDW10:17 pmChicago Midway
Jul 4
MDW4:25 pmChicago Midway
4h 19m
1 stop
EVV8:44 pmEvansville Dress Regional
$1,174
Delta
Jun 28
EVV10:08 amEvansville Dress Regional
8h 23m
2 stops
MDW6:31 pmChicago Midway
Jul 4
MDW4:25 pmChicago Midway
4h 19m
1 stop
EVV8:44 pmEvansville Dress Regional
$1,179

Allegiant Air flights from Evansville to Chicago Midway Airport

Our best Allegiant Air deals on Evansville to Chicago Midway Airport flight tickets
Allegiant Air
Jun 12
EVV11:46 amEvansville Dress Regional
8h 47m
1 stop
MDW8:33 pmChicago Midway
Jun 14
MDW2:46 pmChicago Midway
29h 04m
2 stops
EVV7:50 pmEvansville Dress Regional
$442
Allegiant Air
Jun 29
EVV11:46 amEvansville Dress Regional
8h 47m
1 stop
MDW8:33 pmChicago Midway
Jul 10
MDW3:28 pmChicago Midway
39h 55m
2 stops
EVV7:23 amEvansville Dress Regional
$443
Allegiant Air
Jul 3
EVV3:07 pmEvansville Dress Regional
5h 18m
1 stop
MDW8:25 pmChicago Midway
Jul 10
MDW3:28 pmChicago Midway
39h 55m
2 stops
EVV7:23 amEvansville Dress Regional
$451

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 May 22, 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

Cheapest round-trip

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 6/19

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Sat 6/27

6:00 am-9:20 am

2 stops27h 20m

$402

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 6/12

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Fri 6/19

8:20 pm-3:49 pm

2 stops19h 29m

$417

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/3

3:07 pm-8:25 pm

1 stop5h 18m

Chicago Midway

Sun 7/5

6:00 am-7:43 am

2 stops25h 43m

$425

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 6/12

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Sun 6/14

2:46 pm-7:50 pm

2 stops29h 04m

$442

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 6/29

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Fri 7/10

3:28 pm-7:23 am

2 stops39h 55m

$443

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 6/29

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Tue 7/7

6:00 am-3:49 pm

2 stops33h 49m

$446

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/3

3:07 pm-8:25 pm

1 stop5h 18m

Chicago Midway

Fri 7/10

3:28 pm-7:23 am

2 stops39h 55m

$451

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/3

3:07 pm-8:25 pm

1 stop5h 18m

Chicago Midway

Tue 7/7

6:00 am-3:49 pm

2 stops33h 49m

$454

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 6/29

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Sun 7/5

2:48 pm-7:43 am

2 stops16h 55m

$481
Quickest round-trip

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 7/3

3:07 pm-8:25 pm

1 stop5h 18m

Chicago Midway

Sun 7/5

2:48 pm-7:43 am

2 stops16h 55m

$489

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

6h 09m

Direct flights

None
The fastest flight from Evansville to Chicago Midway Airport takes 6h 09m
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

Frequently asked questions about flying from Evansville to Chicago Midway Airport

  • 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 6h 09m.

  • 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?

Book flights to Chicago if you plan to visit one of these locations
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Benton Harbor
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Munster
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Crown Point
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Saint John

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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