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Cheap flights from Evansville to Chicago from $211

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 10/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Evansville to Chicago (EVV-MDW)

Cheap round-trip flights

Delta Logo
6:02 am - 12:28 pmEVV-MDW
6h 26m2 stops
Delta Logo
1:08 pm - 9:53 pmMDW-EVV
8h 45m2 stops
$1,116Delta
Find Deal
Fri, Oct 31 - Sun, Nov 2
Delta Logo
6:10 am - 12:28 pmEVV-MDW
6h 18m2 stops
Delta Logo
1:08 pm - 9:49 pmMDW-EVV
8h 41m2 stops
$1,156Delta
Find Deal
Tue, Sep 9 - Sat, Sep 13
Delta Logo
10:14 am - 6:35 pmEVV-MDW
8h 21m2 stops
Delta Logo
12:43 pm - 5:21 pmMDW-EVV
4h 38m1 stop
$1,219Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
10:14 am - 6:35 pmEVV-MDW
8h 21m2 stops
Delta Logo
1:08 pm - 9:49 pmMDW-EVV
8h 41m2 stops
$1,223Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
1:17 pm - 5:35 pmEVV-MDW
4h 18m1 stop
Delta Logo
10:35 am - 5:21 pmMDW-EVV
6h 46m1 stop
$1,323Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
5:00 pm - 9:26 pmEVV-MDW
4h 26m1 stop
Delta Logo
12:43 pm - 5:21 pmMDW-EVV
4h 38m1 stop
$1,401Delta
Find Deal
Mon, Sep 8 - Fri, Sep 12

Delta flights from Evansville to Chicago Midway Airport

Our best Delta deals on Evansville to Chicago Midway Airport flight tickets
Delta
Oct 31
EVV6:02 amEvansville Dress Regional
6h 26m
2 stops
MDW12:28 pmChicago Midway
Nov 2
MDW1:08 pmChicago Midway
8h 45m
2 stops
EVV9:53 pmEvansville Dress Regional
$1,116
Find similar
Delta
Sep 9
EVV6:10 amEvansville Dress Regional
6h 18m
2 stops
MDW12:28 pmChicago Midway
Sep 13
MDW1:08 pmChicago Midway
8h 41m
2 stops
EVV9:49 pmEvansville Dress Regional
$1,156
Find similar
Delta
Oct 3
EVV10:14 amEvansville Dress Regional
8h 21m
2 stops
MDW6:35 pmChicago Midway
Oct 5
MDW12:43 pmChicago Midway
4h 38m
1 stop
EVV5:21 pmEvansville Dress Regional
$1,219
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 August 26, 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 10/31

6:02 am-12:28 pm

2 stops6h 26m

Chicago Midway

Sun 11/2

1:08 pm-9:53 pm

2 stops8h 45m

$1,116

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 9/9

6:10 am-12:28 pm

2 stops6h 18m

Chicago Midway

Sat 9/13

1:08 pm-9:49 pm

2 stops8h 41m

$1,156

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 10/3

10:14 am-6:35 pm

2 stops8h 21m

Chicago Midway

Sun 10/5

12:43 pm-5:21 pm

1 stop4h 38m

$1,219

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 10/3

10:14 am-6:35 pm

2 stops8h 21m

Chicago Midway

Sun 10/5

1:08 pm-9:49 pm

2 stops8h 41m

$1,223

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 9/23

1:17 pm-5:35 pm

1 stop4h 18m

Chicago Midway

Tue 9/30

10:35 am-5:21 pm

1 stop6h 46m

$1,323

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 9/8

5:00 pm-9:26 pm

1 stop4h 26m

Chicago Midway

Fri 9/12

12:43 pm-5:21 pm

1 stop4h 38m

$1,401

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 10/5

10:25 am-4:33 pm

2 stops30h 08m

$211

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 10/5

10:25 am-3:53 pm

3 stops29h 28m

$329

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 11/25

12:14 pm-1:21 pm

2 stops25h 07m

$334

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 10/7

10:20 am-6:25 pm

2 stops8h 05m

$558

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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?

Allegiant Air and Delta are the most popular carriers 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

Direct flights

None
There are no direct flights from Evansville to Chicago Midway Airport. There are no popular flight routes from Evansville to Chicago Midway Airport.
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  • 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 18m.

  • 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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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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