EVV - CHI

$145 Find Cheap Flights from Evansville to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Evansville to Chicago departing on 5/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Evansville to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Evansville to Chicago, as well as popular online travel agencies
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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$359
Multiple Airlines
Thu 5/7Sun 5/10
EVV - ORD • 2 stops
Cheapest non-stop
$385
American Airlines
Wed 6/3Sat 6/6
EVV - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy offers budget travel with carry-on.
Expect no seat assignment until check-in with Basic Economy.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with American Airlines. Average duration is 1h 54m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
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We hope you love your trip to Chicago!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Evansville to Chicago (EVV-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Evansville to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Evansville to Chicago

Thu, May 7 - Sun, May 10
Multiple Airlines Logo
3:22 pm - 12:54 pm
EVV
-
ORD
21h 32m
2 stops
Multiple Airlines Logo
8:30 am - 7:03 am
ORD
-
EVV
22h 33m
1 stop
$359Multiple Airlines
Wed, Jun 3 - Sat, Jun 6
American Airlines Logo
6:50 am - 8:39 am
EVV
-
ORD
1h 49mnonstop
American Airlines Logo
4:49 pm - 6:15 pm
ORD
-
EVV
1h 26mnonstop
$385American Airlines
Wed, Jun 3 - Sat, Jun 6
American Airlines Logo
12:46 pm - 7:48 pm
EVV
-
ORD
7h 02m
1 stop
American Airlines Logo
4:49 pm - 6:15 pm
ORD
-
EVV
1h 26mnonstop
$395American Airlines
Mon, Jun 1 - Tue, Jun 2
Multiple Airlines Logo
8:29 am - 8:40 pm
EVV
-
MDW
12h 11m
1 stop
Multiple Airlines Logo
3:07 pm - 3:49 pm
MDW
-
EVV
24h 42m
2 stops
$397Multiple Airlines
Wed, Jun 3 - Sat, Jun 6
American Airlines Logo
12:46 pm - 5:40 pm
EVV
-
ORD
4h 54m
1 stop
American Airlines Logo
8:48 am - 4:08 pm
ORD
-
EVV
7h 20m
1 stop
$405American Airlines
Sun, May 3 - Wed, May 6
Multiple Airlines Logo
4:13 pm - 11:19 am
EVV
-
ORD
43h 06m
2 stops
Multiple Airlines Logo
3:55 pm - 2:32 pm
ORD
-
EVV
22h 37m
1 stop
$411Multiple Airlines
Sat, Jun 27 - Sun, Jun 28
American Airlines Logo
6:50 am - 8:39 am
EVV
-
ORD
1h 49mnonstop
American Airlines Logo
10:40 pm - 12:01 am
ORD
-
EVV
1h 21mnonstop
$422American Airlines
Sat, May 9 - Tue, May 12
Delta Logo
10:10 am - 6:33 pm
EVV
-
MDW
8h 23m
2 stops
Delta Logo
1:22 pm - 9:44 pm
MDW
-
EVV
8h 22m
2 stops
$1,495Delta
Sat, May 2 - Tue, May 5
Delta Logo
10:05 am - 5:58 pm
EVV
-
MDW
7h 53m
2 stops
Delta Logo
9:27 am - 5:18 pm
MDW
-
EVV
7h 51m
2 stops
$1,535Delta
Sat, May 9 - Mon, May 11
Delta Logo
10:10 am - 4:32 pm
EVV
-
MDW
6h 22m
1 stop
Delta Logo
1:22 pm - 9:44 pm
MDW
-
EVV
8h 22m
2 stops
$1,548Delta
Booking Insights

KAYAK's insights & trends for Evansville to Chicago flights

Get data-powered insights and trends into flights from Evansville to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Evansville to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Evansville to Chicago departing in May.

What is the cheapest Evansville to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Evansville to Chicago costs $402 on the route between Evansville (EVV) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Evansville to Chicago?

The average price of all round-trip flights from Evansville to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Wednesday and more expensive on a Sunday. On your return trip to Evansville, you should consider flying back on a Friday, and avoid Mondays for better deals.

Expert advice

Expert advice for your flight from Evansville to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Robert Schrader

Robert Schrader

Expert on Japan Airlines

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Duncan Madden

Duncan Madden

Expert on British Airways

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Good to know

Low seasonJune
Cheapest flight$145
Best time to beat the crowds with an average 58% drop in price.
Most popular time to fly with an average 37% increase in price.
Flight from Evansville to Chicago O'Hare Airport

When to book flights from Evansville to Chicago

Are your dates flexible? Find out the best times to travel from Evansville to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Evansville to Chicago

  • What is the cheapest flight from Evansville to Chicago?

    In the last 3 days, the lowest price for a flight from Evansville to Chicago was $145 for a one-way ticket and $359 for a round-trip.

  • Do I need a passport to fly between Evansville and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Evansville to Chicago?

    On your way to Chicago, you’ll fly out from Evansville Dress Regional. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Evansville to Chicago?

    American Airlines, and Delta offer inflight Wi-Fi service on the Evansville to Chicago flight route.

  • Which aircraft models fly most regularly from Evansville to Chicago?

    The Embraer 170 is the aircraft model that flies most regularly on the Evansville to Chicago flight route.

  • Which airline alliances offer flights from Evansville to Chicago?

    oneworld is the only airline alliance operating flights between Evansville and Chicago.

  • On which days can I fly direct from Evansville to Chicago?

    There are nonstop flights from Evansville to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Evansville to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Evansville to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Evansville to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Evansville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Evansville to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Evansville with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Evansville to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Evansville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Evansville to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $404 or less one-way and $459 or less round-trip.

Prefer to fly direct from Evansville to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Evansville Dress Regional to Chicago.
Find which airlines fly direct from Evansville Dress Regional Airport to Chicago, which days they fly and book direct flights.

Direct departures

Evansville Dress Regional to Chicago

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago to Evansville Dress Regional

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top airline flying from Evansville to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Evansville to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Evansville to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11584 reviews
7.9Crew
6.9Entertainment
7.2Comfort
6.4Food
7.5Boarding
Airline reviews

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

10.0 ExcellentAnonymous, Apr 2026
GSP - ORD
Read more American Airlines reviews

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Everything you need to know for your flight from Evansville to Chicago

Information on your arrival and departure airports