EVV - CHI

$201 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 9/22. 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

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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Booking Insights
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

Sat, Sep 6 - Tue, Sep 9
American Airlines Logo
7:01 am - 8:51 amEVV-ORD
1h 50mnonstop
American Airlines Logo
8:54 pm - 10:18 pmORD-EVV
1h 24mnonstop
$358American Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9
American Airlines Logo
7:01 am - 8:51 amEVV-ORD
1h 50mnonstop
American Airlines Logo
8:38 am - 1:31 pmORD-EVV
4h 53m1 stop
$368American Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
American Airlines Logo
6:03 am - 7:54 amEVV-ORD
1h 51mnonstop
American Airlines Logo
10:25 pm - 11:49 pmORD-EVV
1h 24mnonstop
$369American Airlines
Find Deal
Sat, Sep 27 - Sun, Sep 28
American Airlines Logo
6:04 pm - 7:50 pmEVV-ORD
1h 46mnonstop
American Airlines Logo
4:15 pm - 5:34 pmORD-EVV
1h 19mnonstop
$370American Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9
American Airlines Logo
1:56 pm - 8:27 pmEVV-ORD
6h 31m1 stop
American Airlines Logo
12:33 pm - 8:28 pmORD-EVV
7h 55m1 stop
$378American Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
American Airlines Logo
6:03 am - 7:54 amEVV-ORD
1h 51mnonstop
American Airlines Logo
6:35 pm - 11:59 pmORD-EVV
5h 24m1 stop
$379American Airlines
Find Deal
Sat, Sep 27 - Sun, Sep 28
American Airlines Logo
7:01 am - 8:51 amEVV-ORD
1h 50mnonstop
American Airlines Logo
7:02 am - 12:23 pmORD-EVV
5h 21m1 stop
$380American Airlines
Find Deal
Tue, Sep 9 - Sat, Sep 13
American Airlines Logo
6:04 pm - 7:50 pmEVV-ORD
1h 46mnonstop
American Airlines Logo
8:54 pm - 10:18 pmORD-EVV
1h 24mnonstop
$385American Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
Delta Logo
12:00 pm - 8:23 pmEVV-ORD
8h 23m2 stops
Delta Logo
1:25 pm - 9:53 pmORD-EVV
8h 28m2 stops
$1,116Delta
Find Deal
Fri, Oct 31 - Sun, Nov 2
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
Expert advice

Expert advice for your flight from Evansville to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Japan Airlines

JAL offers generous baggage allowance: two checked bags up to 23 kg each, plus carry-on.


JAL's Sky Wider economy seats are spacious, especially on 787 aircraft with a 2-4-2 configuration.

British Airways

BA's Euro Traveller fares include a carry-on bag, avoiding surprise fees during booking.


BA's short-haul seats are ergonomic leather, offering comfort with 31-inch pitch on most planes.

American Airlines

Consider Basic Economy for budget travel with carry-on only and no seat assignment until check-in.


Use Main Cabin Extra for early boarding (Group 5) and complimentary alcoholic drinks on short flights.

Our travel experts
Robert Schrader

Robert Schrader

Expert on Japan Airlines

Robert Schrader

Robert Schrader

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.

Read more
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan Madden

Duncan Madden

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
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.

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 $338 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 Friday and more expensive on a Monday. On your return trip to Evansville, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

What is the cheapest month to fly from Evansville to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Evansville to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Evansville to Chicago is June, where tickets cost $178 (return) on average. On the other hand, the most expensive months are October and February, where the average cost of round-trip tickets is $573 and $461 respectively.

Good to know

Low seasonJuly
Cheapest flight$201
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 14% 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 $201 for a one-way ticket and $358 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 $286 or less one-way and $456 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.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
8.0Crew
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

6.0 GoodMitchell, Aug 2025CMH - ORD
Read more American Airlines reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Information on your arrival and departure airports

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