EVV - CHI

$201 Find Cheap Flights from Evansville to Chicago - Compare and Save

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 7/26. 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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Everything you should know

Cheapest round-trip
$339
Allegiant Air
Mon 8/3Thu 8/6
EVV - MDW • 1 stop
Cheapest non-stop
$405
American Airlines
Wed 7/15Wed 7/22
EVV - ORD • Non-stop
Top airlines
Cheapest • from $405 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines. Average duration is 1h 55m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Mon, Aug 3 - Thu, Aug 6
Multiple Airlines Logo
11:41 am - 8:30 pm
EVV
-
MDW
8h 49m
1 stop
Multiple Airlines Logo
2:49 pm - 3:49 pm
MDW
-
EVV
49h 00m
2 stops
$339Multiple Airlines
Fri, Jul 24 - Fri, Jul 31
Multiple Airlines Logo
11:41 am - 8:31 pm
EVV
-
MDW
8h 50m
1 stop
Multiple Airlines Logo
12:11 pm - 3:49 pm
MDW
-
EVV
27h 38m
2 stops
$375Multiple Airlines
Fri, Jul 10 - Fri, Jul 17
Allegiant Air Logo
11:41 am - 8:31 pm
EVV
-
MDW
8h 50m
1 stop
Allegiant Air Logo
3:28 pm - 7:23 am
MDW
-
EVV
39h 55m
2 stops
$395Allegiant Air
Wed, Jul 15 - Wed, Jul 22
American Airlines Logo
6:55 pm - 9:04 pm
EVV
-
ORD
2h 09mnonstop
American Airlines Logo
5:00 pm - 6:25 pm
ORD
-
EVV
1h 25mnonstop
$405American Airlines
Sat, Jul 11 - Sat, Jul 18
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
Tue, Aug 11 - Wed, Aug 26
Delta Logo
6:25 am - 4:15 pm
EVV
-
MDW
9h 50m
1 stop
Delta Logo
6:05 am - 10:01 pm
MDW
-
EVV
15h 56m
1 stop
$445Delta
Sat, Jun 27 - Wed, Jul 1
American Airlines Logo
7:44 pm - 9:35 pm
EVV
-
ORD
1h 51mnonstop
American Airlines Logo
11:00 pm - 12:21 am
ORD
-
EVV
1h 21mnonstop
$449American Airlines
Fri, Jul 17 - Tue, Jul 21
American Airlines Logo
7:08 am - 9:05 am
EVV
-
ORD
1h 57mnonstop
American Airlines Logo
10:36 pm - 11:59 pm
ORD
-
EVV
1h 23mnonstop
$452American Airlines
Sat, Aug 15 - Fri, Aug 28
Multiple Airlines Logo
4:29 pm - 4:00 pm
EVV
-
ORD
23h 31m
2 stops
Multiple Airlines Logo
5:30 pm - 3:49 pm
ORD
-
EVV
22h 19m
1 stop
$458Multiple Airlines
Tue, Aug 11 - Sat, Aug 29
Delta Logo
6:25 am - 4:15 pm
EVV
-
MDW
9h 50m
1 stop
Delta Logo
6:05 am - 2:21 pm
MDW
-
EVV
8h 16m
1 stop
$461Delta
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 August.

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 $474 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 Saturday and more expensive on a Sunday. On your return trip to Evansville, you should consider flying back on a Thursday, 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$201
Best time to beat the crowds with an average 61% drop in price.
Most popular time to fly with an average 26% 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 5 days, the lowest price for a flight from Evansville to Chicago was $201 for a one-way ticket and $339 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?

    Only American Airlines offers 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 $407 or less one-way and $534 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 11660 reviews
6.4Food
7.9Crew
6.8Entertainment
7.5Boarding
7.2Comfort
Airline reviews

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

6.0 GoodJeffrey, Jun 2026
BOS - ORD
Read more American Airlines reviews

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

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

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

Information on your arrival and departure airports