What airlines fly to Chicago?

American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Chicago from Evansville according to our data. American Airlines is the first choice among our users, with 29% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Evansville to Chicago on average per week?

As of January 2026, 27 flights take off from Evansville and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

How many flights depart from Evansville to Chicago on average per day?

As of January 2026, 3 flights take off from Evansville and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 75% of daily flights taking off at noon.

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?

As of January 2026, there is 1 operator available to choose from 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.

$122 Cheap Flights from Evansville to Chicago in 2026

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Find the cheapest flights from Evansville to Chicago

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:46 pm - 10:46 am

EVV

ORD

15h 00m

2 stops

10:19 am - 1:44 pm

ORD

EVV

27h 25m

1 stop

$340Multiple Airlines

Fri, Feb 20 - Sun, Feb 22

6:33 am - 8:20 am

EVV

ORD

1h 47mnonstop

10:31 pm - 11:55 pm

ORD

EVV

1h 24mnonstop

$345American Airlines

Wed, Apr 15 - Sat, Apr 18

7:46 pm - 10:46 am

EVV

ORD

15h 00m

2 stops

2:13 pm - 1:44 pm

ORD

EVV

23h 31m

1 stop

$346Multiple Airlines

Fri, Feb 20 - Sun, Feb 22

7:46 pm - 3:35 pm

EVV

ORD

19h 49m

1 stop

2:13 pm - 1:44 pm

ORD

EVV

23h 31m

1 stop

$348Multiple Airlines

Fri, Feb 20 - Sun, Feb 22

6:56 pm - 11:57 pm

EVV

ORD

5h 01m

1 stop

10:31 pm - 11:55 pm

ORD

EVV

1h 24mnonstop

$355American Airlines

Wed, Apr 15 - Sat, Apr 18

5:10 am - 12:36 pm

EVV

ORD

7h 26m

1 stop

5:00 am - 10:35 am

ORD

EVV

5h 35m

1 stop

$365American Airlines

Wed, Apr 15 - Sat, Apr 18

7:10 am - 9:01 am

EVV

ORD

1h 51mnonstop

7:35 pm - 8:58 pm

ORD

EVV

1h 23mnonstop

$389American Airlines

Tue, Feb 3 - Tue, Feb 10

10:05 am - 5:54 pm

EVV

MDW

7h 49m

2 stops

9:27 am - 5:19 pm

MDW

EVV

7h 52m

2 stops

$1,356Delta

Mon, May 4 - Wed, May 6

5:59 pm - 10:31 pm

EVV

MDW

4h 32m

1 stop

1:28 pm - 10:20 pm

MDW

EVV

8h 52m

2 stops

$1,378Delta

Fri, Feb 13 - Sat, Feb 21

6:00 am - 11:59 am

EVV

MDW

5h 59m

1 stop

4:13 pm - 10:20 pm

MDW

EVV

6h 07m

1 stop

$1,401Delta

Fri, Feb 13 - Sat, Feb 21

American Airlines flights from Evansville to Chicago

Our best American Airlines deals on Evansville to Chicago flight tickets

American Airlines

Mar 10

EVV4:20 pmEvansville Dress Regional

1h 43m

ORD6:03 pmChicago O'Hare Intl

Mar 17

ORD2:33 pmChicago O'Hare Intl

1h 16m

EVV3:49 pmEvansville Dress Regional

$347

American Airlines

Mar 10

EVV6:05 amEvansville Dress Regional

8h 11m

1 stop

ORD2:16 pmChicago O'Hare Intl

Mar 17

ORD10:29 pmChicago O'Hare Intl

1h 17m

EVV11:46 pmEvansville Dress Regional

$357

American Airlines

Mar 10

EVV11:57 amEvansville Dress Regional

6h 00m

1 stop

ORD5:57 pmChicago O'Hare Intl

Mar 17

ORD3:16 pmChicago O'Hare Intl

7h 37m

1 stop

EVV10:53 pmEvansville Dress Regional

$367

Delta flights from Evansville to Chicago

Our best Delta deals on Evansville to Chicago flight tickets

Delta

Feb 7

EVV1:00 pmEvansville Dress Regional

8h 05m

2 stops

ORD9:05 pmChicago O'Hare Intl

Feb 11

ORD10:35 amChicago O'Hare Intl

6h 44m

2 stops

EVV5:19 pmEvansville Dress Regional

$1,356

Delta

Feb 3

EVV6:15 amEvansville Dress Regional

7h 25m

1 stop

ORD1:40 pmChicago O'Hare Intl

Feb 10

ORD10:35 amChicago O'Hare Intl

11h 47m

2 stops

EVV10:22 pmEvansville Dress Regional

$1,378

Delta

Feb 3

EVV6:15 amEvansville Dress Regional

10h 42m

2 stops

ORD4:57 pmChicago O'Hare Intl

Feb 10

ORD6:50 amChicago O'Hare Intl

10h 29m

2 stops

EVV5:19 pmEvansville Dress Regional

$1,384

Fly from

Fly to

Route

Depart

Return

Price

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 2/20

7:46 pm-10:46 am

2 stops15h 00m

Chicago O'Hare Intl

Sun 2/22

10:19 am-1:44 pm

1 stop27h 25m

$340

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 4/15

6:33 am-8:20 am

Nonstop1h 47m

Chicago O'Hare Intl

Sat 4/18

10:31 pm-11:55 pm

Nonstop1h 24m

$345

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 2/20

7:46 pm-10:46 am

2 stops15h 00m

Chicago O'Hare Intl

Sun 2/22

2:13 pm-1:44 pm

1 stop23h 31m

$346

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 2/20

7:46 pm-3:35 pm

1 stop19h 49m

Chicago O'Hare Intl

Sun 2/22

2:13 pm-1:44 pm

1 stop23h 31m

$348

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 4/15

6:56 pm-11:57 pm

1 stop5h 01m

Chicago O'Hare Intl

Sat 4/18

10:31 pm-11:55 pm

Nonstop1h 24m

$355

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 4/15

5:10 am-12:36 pm

1 stop7h 26m

Chicago O'Hare Intl

Sat 4/18

5:00 am-10:35 am

1 stop5h 35m

$365

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Tue 2/3

7:10 am-9:01 am

Nonstop1h 51m

Chicago O'Hare Intl

Tue 2/10

7:35 pm-8:58 pm

Nonstop1h 23m

$389

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 5/4

10:05 am-5:54 pm

2 stops7h 49m

Chicago Midway

Wed 5/6

9:27 am-5:19 pm

2 stops7h 52m

$1,356

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 2/13

5:59 pm-10:31 pm

1 stop4h 32m

Chicago Midway

Sat 2/21

1:28 pm-10:20 pm

2 stops8h 52m

$1,378

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 2/13

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Sat 2/21

4:13 pm-10:20 pm

1 stop6h 07m

$1,401

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 $495. 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 $1,115.

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 $557. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,209.

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	$328
Fastest flight time	1h 43m
Direct flights	Mon, Wed, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Evansville in the past 72 hours is $328. The best round-trip flight deal from Evansville to Chicago found on momondo in the last 72 hours is $502.

The fastest flight from Evansville to Chicago takes 1h 43m

Direct flights go from Evansville to Chicago on Monday, Wednesday, 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

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?
As of January 2026, there is 1 operator available to choose from 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Evansville to Chicago is Embraer 170 (48.28% of total bookings). The next most popular plane models are Airbus A320-100/200 (10.34%), Boeing 737 MAX 8 (6.90%), and Canadair (Bombardier) Regional Jet (6.90%).
What is the most popular airline from Evansville to Chicago?
momondo data reveals that the most frequently booked airline on the route from Evansville to Chicago is American Airlines, representing 100% of all bookings.

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 Airlines	PriceFrom $191	Free Cancellation	Rating 7.2 11,197 reviews		Search American Airlines flights

American Airlines Flights From Evansville to Chicago
American Airlines flies from Evansville to Chicago around 13 times per week, with 11,197 momondo users rating the airline 7.2/10. The cheapest American Airlines deal from Evansville to Chicago in the last 72 hours was $191 (round-trip), much lower than the average airfare cost of $436 for American Airlines flights on this route.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Bostonfrom $50

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Flights to Dallasfrom $58

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Flights to Denverfrom $55

Cheap flights from Evansville to Chicago from $122

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 4/20. 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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Big names and deals

Filter for what you want

Filter for what you want

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American Airlines flights from Evansville to Chicago

Our best American Airlines deals on Evansville to Chicago flight tickets

Delta flights from Evansville to Chicago

Our best Delta deals on Evansville to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Evansville to 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?

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 $557. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,209.

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.

What airlines fly to Chicago?

How many flights depart from Evansville to Chicago on average per day?

As of January 2026, 3 flights take off from Evansville and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 75% of daily flights taking off at noon.

How many flights depart from Evansville to Chicago on average per week?

As of January 2026, 27 flights take off from Evansville and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

When to book flights from Evansville to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Evansville Dress Regional to Chicago by plane?

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

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?

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

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

American Airlines Flights From Evansville to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights 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?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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