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Cheap flights from Evansville to Chicago from $108

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 12/8. 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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Multiple Airlines Logo
5:35 pm - 11:06 pmEVV-ORD
29h 31m1 stop
Multiple Airlines Logo
7:20 am - 4:55 pmORD-EVV
9h 35m1 stop
$235Multiple Airlines
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Mon, Dec 1 - Mon, Dec 8
Multiple Airlines Logo
3:27 pm - 1:16 pmEVV-ORD
21h 49m1 stop
Multiple Airlines Logo
3:20 pm - 6:56 pmORD-EVV
27h 36m2 stops
$242Multiple Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
5:35 pm - 6:46 pmEVV-ORD
25h 11m2 stops
Multiple Airlines Logo
7:20 am - 4:55 pmORD-EVV
9h 35m1 stop
$245Multiple Airlines
Find Deal
Mon, Dec 1 - Mon, Dec 8
American Airlines Logo
4:18 pm - 6:10 pmEVV-ORD
1h 52mnonstop
American Airlines Logo
2:23 pm - 3:47 pmORD-EVV
1h 24mnonstop
$369American Airlines
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Thu, Feb 12 - Sat, Feb 14
American Airlines Logo
4:18 pm - 6:10 pmEVV-ORD
1h 52mnonstop
American Airlines Logo
6:48 pm - 11:56 pmORD-EVV
5h 08m1 stop
$379American Airlines
Find Deal
Thu, Feb 12 - Sat, Feb 14
American Airlines Logo
6:57 pm - 11:54 pmEVV-ORD
4h 57m1 stop
American Airlines Logo
1:54 pm - 6:32 pmORD-EVV
4h 38m1 stop
$389American Airlines
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Thu, Feb 12 - Sat, Feb 14
American Airlines Logo
6:03 pm - 7:50 pmEVV-ORD
1h 47mnonstop
American Airlines Logo
4:08 pm - 5:33 pmORD-EVV
1h 25mnonstop
$407American Airlines
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Fri, Dec 5 - Sun, Dec 7
Delta Logo
6:00 am - 8:43 pmEVV-ORD
14h 43m2 stops
Delta Logo
6:30 am - 10:22 pmORD-EVV
15h 52m2 stops
$578Delta
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:59 pm - 8:54 amEVV-MDW
14h 55m2 stops
Delta Logo
1:28 pm - 5:19 pmMDW-EVV
27h 51m2 stops
$578Delta
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:59 pm - 8:54 amEVV-MDW
14h 55m2 stops
Delta Logo
1:28 pm - 5:19 pmMDW-EVV
27h 51m2 stops
$594Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4

American Airlines flights from Evansville to Chicago

Our best American Airlines deals on Evansville to Chicago flight tickets
American Airlines
Feb 12
EVV4:18 pmEvansville Dress Regional
1h 52m
ORD6:10 pmChicago O'Hare Intl
Feb 14
ORD2:23 pmChicago O'Hare Intl
1h 24m
EVV3:47 pmEvansville Dress Regional
$369
Find similar
American Airlines
Feb 12
EVV4:18 pmEvansville Dress Regional
1h 52m
ORD6:10 pmChicago O'Hare Intl
Feb 14
ORD6:48 pmChicago O'Hare Intl
5h 08m
1 stop
EVV11:56 pmEvansville Dress Regional
$379
Find similar
American Airlines
Feb 12
EVV6:57 pmEvansville Dress Regional
4h 57m
1 stop
ORD11:54 pmChicago O'Hare Intl
Feb 14
ORD1:54 pmChicago O'Hare Intl
4h 38m
1 stop
EVV6:32 pmEvansville Dress Regional
$389
Find similar

Delta flights from Evansville to Chicago

Our best Delta deals on Evansville to Chicago flight tickets
Delta
Mar 3
EVV6:00 amEvansville Dress Regional
14h 43m
2 stops
ORD8:43 pmChicago O'Hare Intl
Mar 4
ORD6:30 amChicago O'Hare Intl
15h 52m
2 stops
EVV10:22 pmEvansville Dress Regional
$578
Find similar
Delta
Mar 3
EVV5:59 pmEvansville Dress Regional
14h 55m
2 stops
MDW8:54 amChicago Midway
Mar 4
MDW1:28 pmChicago Midway
27h 51m
2 stops
EVV5:19 pmEvansville Dress Regional
$594
Find similar
Delta
Mar 3
EVV11:10 amEvansville Dress Regional
12h 47m
1 stop
ORD11:57 pmChicago O'Hare Intl
Mar 4
ORD10:35 amChicago O'Hare Intl
11h 47m
2 stops
EVV10:22 pmEvansville Dress Regional
$600
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Evansville to Chicago 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 November 6, 2025.
Use the filters below to find and compare flights from Evansville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Mon 12/1

5:35 pm-11:06 pm

1 stop29h 31m

Chicago O'Hare Intl

Mon 12/8

7:20 am-4:55 pm

1 stop9h 35m

$235

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 12/11

3:27 pm-1:16 pm

1 stop21h 49m

Chicago O'Hare Intl

Sun 12/14

3:20 pm-6:56 pm

2 stops27h 36m

$242

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Mon 12/1

5:35 pm-6:46 pm

2 stops25h 11m

Chicago O'Hare Intl

Mon 12/8

7:20 am-4:55 pm

1 stop9h 35m

$245

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 2/12

4:18 pm-6:10 pm

Nonstop1h 52m

Chicago O'Hare Intl

Sat 2/14

2:23 pm-3:47 pm

Nonstop1h 24m

$369

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 2/12

4:18 pm-6:10 pm

Nonstop1h 52m

Chicago O'Hare Intl

Sat 2/14

6:48 pm-11:56 pm

1 stop5h 08m

$379

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 2/12

6:57 pm-11:54 pm

1 stop4h 57m

Chicago O'Hare Intl

Sat 2/14

1:54 pm-6:32 pm

1 stop4h 38m

$389

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 12/5

6:03 pm-7:50 pm

Nonstop1h 47m

Chicago O'Hare Intl

Sun 12/7

4:08 pm-5:33 pm

Nonstop1h 25m

$407

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Tue 3/3

6:00 am-8:43 pm

2 stops14h 43m

Chicago O'Hare Intl

Wed 3/4

6:30 am-10:22 pm

2 stops15h 52m

$578

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 3/3

5:59 pm-8:54 am

2 stops14h 55m

Chicago Midway

Wed 3/4

1:28 pm-5:19 pm

2 stops27h 51m

$578

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 3/3

5:59 pm-8:54 am

2 stops14h 55m

Chicago Midway

Wed 3/4

1:28 pm-5:19 pm

2 stops27h 51m

$594

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

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 typical price of a round-trip flight between Evansville and Chicago?

What is the cheapest month to fly to Chicago?

The month of June is, on average, the cheapest month to fly to Chicago from Evansville, with most prices found around $178. If you’re not able to fly to Chicago in June, then May is your next best option. Flight prices from Evansville to Chicago during May average around $191.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $542. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Evansville to Chicago for around $772.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Evansville to Chicago during this time can be as low as $572. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $925.

What is the cheapest Evansville Dress Regional to Chicago flight route?

Fly from Evansville Dress Regional to Chicago O'Hare Intl for the best Evansville Dress Regional - Chicago flight prices

What cabin class options are available on Evansville Dress Regional to Chicago flights?

There are 4 cabin classes available to choose from on Evansville Dress Regional to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Evansville to Chicago flights?

No. A direct flight is the cheapest option for a flight between Evansville to Chicago.

When to book flights from Evansville to Chicago

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

Cheap Evansville to Chicago (EVV to CHI) flight deals and tips

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

Best Price Found

$308

Fastest flight time

1h 43m

Direct flights

Mon, Tue, Wed, Thu, Fri and Sat

Airports in Chicago

1 airport
The best one-way flight to Chicago from Evansville in the past 72 hours is $308. The best round-trip flight deal from Evansville to Chicago found on momondo in the last 72 hours is $385.
The fastest flight from Evansville to Chicago takes 1h 43m
Direct flights go from Evansville to Chicago on Monday, Tuesday, Wednesday, Thursday, Friday and Saturday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

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

    Chicago is 269.4 mi away from Evansville Dress Regional. In terms of flight time, this usually takes a little over 1h 43m.

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

    Prices for flights from Evansville Dress Regional Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Evansville Dress Regional Airport to Chicago?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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.

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Evansville to Chicago?

  • What is the most popular airline from Evansville to Chicago?

Best airlines flying from Evansville to Chicago

Compare and see reviews for airlines that fly from Evansville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $246Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights

  • American Airlines Flights From Evansville to Chicago

    American Airlines flies from Evansville to Chicago around 8 times per week, with 11,040 momondo users rating the airline 7.2/10. The cheapest American Airlines deal from Evansville to Chicago in the last 72 hours was $246 (round-trip), much lower than the average airfare cost of $407 for American Airlines flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Evansville to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. All flights to Chicago from Evansville on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Evansville to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Chicago from Evansville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport