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Cheap flights from Evansville to Chicago from $187

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 8/23. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Evansville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:15 am - 11:50 pm
EVV
-
ORD
15h 35m
1 stop
Multiple Airlines Logo
2:03 pm - 7:40 am
ORD
-
EVV
17h 37m
2 stops
$397Multiple Airlines
Thu, Nov 12 - Sat, Nov 14
American Airlines Logo
7:52 pm - 9:49 pm
EVV
-
ORD
1h 57mnonstop
American Airlines Logo
3:59 pm - 5:20 pm
ORD
-
EVV
1h 21mnonstop
$405American Airlines
Sat, Aug 1 - Sat, Aug 8
Multiple Airlines Logo
8:15 am - 11:50 pm
EVV
-
ORD
15h 35m
1 stop
Multiple Airlines Logo
4:44 pm - 7:40 am
ORD
-
EVV
14h 56m
1 stop
$415Multiple Airlines
Thu, Nov 12 - Sat, Nov 14
American Airlines Logo
7:52 pm - 9:49 pm
EVV
-
ORD
1h 57mnonstop
American Airlines Logo
5:57 pm - 7:22 pm
ORD
-
EVV
1h 25mnonstop
$427American Airlines
Sat, Jul 25 - Sat, Aug 1
American Airlines Logo
6:00 am - 8:01 am
EVV
-
ORD
2h 01mnonstop
American Airlines Logo
4:20 pm - 5:41 pm
ORD
-
EVV
1h 21mnonstop
$452American Airlines
Sat, Aug 8 - Mon, Aug 10
American Airlines Logo
7:52 pm - 9:49 pm
EVV
-
ORD
1h 57mnonstop
American Airlines Logo
10:36 pm - 11:59 pm
ORD
-
EVV
1h 23mnonstop
$454American Airlines
Sat, Aug 1 - Sun, Aug 2
American Airlines Logo
12:46 pm - 7:51 pm
EVV
-
ORD
7h 05m
1 stop
American Airlines Logo
3:59 pm - 5:20 pm
ORD
-
EVV
1h 21mnonstop
$472American Airlines
Sat, Aug 1 - Sat, Aug 8
Delta Logo
10:18 am - 6:07 pm
EVV
-
MDW
7h 49m
2 stops
Delta Logo
9:19 am - 8:39 pm
MDW
-
EVV
11h 20m
2 stops
$1,395Delta
Sat, Jul 25 - Sat, Aug 1
Delta Logo
10:04 am - 4:15 pm
EVV
-
MDW
6h 11m
1 stop
Delta Logo
12:46 pm - 5:19 pm
MDW
-
EVV
4h 33m
1 stop
$1,413Delta
Fri, Aug 28 - Sun, Aug 30
Delta Logo
10:04 am - 6:33 pm
EVV
-
MDW
8h 29m
2 stops
Delta Logo
12:46 pm - 5:19 pm
MDW
-
EVV
4h 33m
1 stop
$1,414Delta
Fri, Aug 28 - Sun, Aug 30

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American Airlines flights from Evansville to Chicago

Our best American Airlines deals on Evansville to Chicago flight tickets
American Airlines
Aug 1
EVV7:52 pmEvansville Dress Regional
1h 57m
ORD9:49 pmChicago O'Hare Intl
Aug 8
ORD3:59 pmChicago O'Hare Intl
1h 21m
EVV5:20 pmEvansville Dress Regional
$405
American Airlines
Jul 25
EVV7:52 pmEvansville Dress Regional
1h 57m
ORD9:49 pmChicago O'Hare Intl
Aug 1
ORD5:57 pmChicago O'Hare Intl
1h 25m
EVV7:22 pmEvansville Dress Regional
$427
American Airlines
Jul 8
EVV7:08 amEvansville Dress Regional
1h 57m
ORD9:05 amChicago O'Hare Intl
Jul 14
ORD10:36 pmChicago O'Hare Intl
1h 23m
EVV11:59 pmEvansville Dress Regional
$449

Delta flights from Evansville to Chicago

Our best Delta deals on Evansville to Chicago flight tickets
Delta
Jul 3
EVV5:58 pmEvansville Dress Regional
4h 19m
1 stop
MDW10:17 pmChicago Midway
Jul 6
MDW12:50 pmChicago Midway
4h 28m
1 stop
EVV5:18 pmEvansville Dress Regional
$1,291
Delta
Jul 3
EVV1:46 pmEvansville Dress Regional
6h 45m
2 stops
ORD8:31 pmChicago O'Hare Intl
Jul 6
ORD11:23 amChicago O'Hare Intl
5h 55m
1 stop
EVV5:18 pmEvansville Dress Regional
$1,296
Delta
Jul 3
EVV1:46 pmEvansville Dress Regional
6h 45m
2 stops
ORD8:31 pmChicago O'Hare Intl
Jul 6
ORD7:01 amChicago O'Hare Intl
10h 17m
2 stops
EVV5:18 pmEvansville Dress Regional
$1,301

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 June 29, 2026.
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

Cheapest round-trip

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 11/12

8:15 am-11:50 pm

1 stop15h 35m

Chicago O'Hare Intl

Sat 11/14

2:03 pm-7:40 am

2 stops17h 37m

$397
Quickest round-trip

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 8/1

7:52 pm-9:49 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sat 8/8

3:59 pm-5:20 pm

Nonstop1h 21m

$405

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 11/12

8:15 am-11:50 pm

1 stop15h 35m

Chicago O'Hare Intl

Sat 11/14

4:44 pm-7:40 am

1 stop14h 56m

$415

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 7/25

7:52 pm-9:49 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sat 8/1

5:57 pm-7:22 pm

Nonstop1h 25m

$427

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 8/8

6:00 am-8:01 am

Nonstop2h 01m

Chicago O'Hare Intl

Mon 8/10

4:20 pm-5:41 pm

Nonstop1h 21m

$452

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 8/1

7:52 pm-9:49 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 8/2

10:36 pm-11:59 pm

Nonstop1h 23m

$454

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 8/1

12:46 pm-7:51 pm

1 stop7h 05m

Chicago O'Hare Intl

Sat 8/8

3:59 pm-5:20 pm

Nonstop1h 21m

$472

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 7/25

10:18 am-6:07 pm

2 stops7h 49m

Chicago Midway

Sat 8/1

9:19 am-8:39 pm

2 stops11h 20m

$1,395

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 8/28

10:04 am-4:15 pm

1 stop6h 11m

Chicago Midway

Sun 8/30

12:46 pm-5:19 pm

1 stop4h 33m

$1,413

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 8/28

10:04 am-6:33 pm

2 stops8h 29m

Chicago Midway

Sun 8/30

12:46 pm-5:19 pm

1 stop4h 33m

$1,414

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 cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Evansville, with most prices found around $0. If you’re not able to fly to Chicago in May, then January is your next best option. Flight prices from Evansville to Chicago during January average around $0.

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 Saturday when prices can be found for as low as $512. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Evansville to Chicago for around $1,165.

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 evening. Flights from Evansville to Chicago during this time can be as low as $569. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,300.

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 to Chicago flights?

There are 4 cabin classes available to choose from on Evansville 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

$347

Fastest flight time

2h 01m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Evansville in the past 72 hours is $347. The best round-trip flight deal from Evansville to Chicago found on momondo in the last 72 hours is $532.
The fastest flight from Evansville to Chicago takes 2h 01m
Direct flights go from Evansville to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Evansville there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Evansville to Chicago

  • 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 2h 01m.

  • 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 $331Free CancellationRating
7.1
11,766 reviews
Search American Airlines flights

  • American Airlines Flights From Evansville to Chicago

    American Airlines flies from Evansville to Chicago around 11 times per week, with 11,768 momondo users rating the airline 7.1/10. The cheapest American Airlines deal from Evansville to Chicago in the last 72 hours was $331 (round-trip), much lower than the average airfare cost of $445 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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