EVV - CHI

$105 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 12/8. 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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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

Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
5:35 pm - 2:45 pmEVV-ORD
21h 10m2 stops
Multiple Airlines Logo
6:00 am - 4:55 pmORD-EVV
10h 55m1 stop
$225Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
5:35 pm - 9:33 pmEVV-ORD
27h 58m1 stop
Multiple Airlines Logo
6:00 am - 4:55 pmORD-EVV
10h 55m1 stop
$236Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
5:35 pm - 11:25 pmEVV-MDW
29h 50m2 stops
Multiple Airlines Logo
9:32 am - 4:55 pmMDW-EVV
7h 23m1 stop
$252Multiple Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
7:10 am - 8:53 amEVV-ORD
1h 43mnonstop
American Airlines Logo
5:36 pm - 6:53 pmORD-EVV
1h 17mnonstop
$331American Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
7:10 am - 8:53 amEVV-ORD
1h 43mnonstop
American Airlines Logo
5:40 pm - 10:51 pmORD-EVV
5h 11m1 stop
$341American Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
11:50 am - 5:52 pmEVV-ORD
6h 02m1 stop
American Airlines Logo
6:46 am - 11:25 amORD-EVV
4h 39m1 stop
$351American Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
7:10 am - 8:53 amEVV-ORD
1h 43mnonstop
American Airlines Logo
5:00 am - 11:25 amORD-EVV
6h 25m1 stop
$368American Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
10:05 am - 8:54 amEVV-MDW
22h 49m2 stops
Delta Logo
5:25 pm - 4:56 pmMDW-EVV
23h 31m1 stop
$691Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
6:00 am - 4:25 pmEVV-MDW
10h 25m1 stop
Delta Logo
5:25 pm - 4:56 pmMDW-EVV
23h 31m1 stop
$693Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
10:05 am - 8:54 amEVV-MDW
22h 49m2 stops
Delta Logo
1:00 pm - 4:56 pmMDW-EVV
27h 56m2 stops
$699Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Top routes
EVV-ORD
Cheapest
EVV-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 53% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$225
Multiple Airlines
Mon 10/27Fri 10/31
EVV - ORD • 2 stops
Cheapest non-stop
$331
Typical prices: $728-$801
American Airlines
Tue 11/11Tue 11/18
EVV - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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 $361 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 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 $766 and $461 respectively.

Find deals
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.

Read more about Japan Airlinesby Robert Schrader
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.

Read more about British Airwaysby Duncan Madden
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.

Read more about American Airlinesby Harriet Baskas
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

Good to know

Low seasonJuly
Cheapest flight$105
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 21% 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 $105 for a one-way ticket and $225 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 $288 or less one-way and $496 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 11042 reviews
6.4Food
7.5Boarding
7.2Comfort
8.0Crew
6.9Entertainment
Airline reviews

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

8.0 ExcellentRachel, Oct 2025CLE - ORD
Read more American Airlines reviews

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

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

Information on your arrival and departure airports

Evansville (EVV)

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