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Evansville

$182+ Cheap flights from Chicago (CHI) to Evansville (EVV)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EVV
May 24 — May 311
Sun 5/24
Sun 5/31
1 adult, Economy
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Cheap flight deals from Chicago to Evansville

Cheapest flights from Chicago to Evansville
Explore the most affordable flight options available from Chicago to Evansville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.

This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:40 pm
ORD
-
EVV
Nonstop1h 19m
American Airlines
Wed 6/106:32 pm
EVV
-
ORD
Nonstop2h 01m
American Airlines
Deal found 4/19$386
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:40 pm
ORD
-
EVV
Nonstop1h 19m
American Airlines
Sat 5/305:24 am
EVV
-
ORD
1 stop6h 54m
American Airlines
Deal found 4/19$395
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:33 pm
ORD
-
EVV
2 stops20h 16m
Multiple Airlines
Fri 5/298:44 pm
EVV
-
ORD
1 stop26h 29m
Multiple Airlines
Deal found 4/23$406
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:38 pm
ORD
-
EVV
Nonstop1h 20m
American Airlines
Wed 5/276:50 am
EVV
-
ORD
Nonstop1h 49m
American Airlines
Deal found 4/22$407
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:38 pm
ORD
-
EVV
Nonstop1h 20m
American Airlines
Sat 5/235:24 am
EVV
-
ORD
1 stop6h 54m
American Airlines
Deal found 4/21$417
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:40 pm
ORD
-
EVV
Nonstop1h 19m
American Airlines
Sun 5/316:50 am
EVV
-
ORD
Nonstop1h 49m
American Airlines
Deal found 4/24$422

Find flight deals from Chicago to Evansville

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Evansville (EVV). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$395
(American Airlines)

One-way from

$182
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Evansville Dress Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Evansville Dress Regional flights.
Search Deals
From Chicago (CHI) to Evansville Dress Regional
Search Deals
One-way flight from Chicago (CHI) to Evansville Dress Regional
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Evansville that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2026.
Use the filters below to find and compare flights from Chicago to Evansville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 5/22

7:33 pm-3:49 pm

2 stops20h 16m

Evansville Dress Regional

Fri 5/29

8:44 pm-11:13 pm

1 stop26h 29m

$406
Quickest round-trip

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 5/5

4:29 pm-5:53 pm

Nonstop1h 24m

Evansville Dress Regional

Sat 5/9

6:23 pm-8:13 pm

Nonstop1h 50m

$429

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 5/24

5:10 am-12:21 pm

1 stop7h 11m

Evansville Dress Regional

Sun 5/31

6:50 am-8:39 am

Nonstop1h 49m

$432

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 6/16

5:10 am-12:21 pm

1 stop7h 11m

Evansville Dress Regional

Thu 6/18

4:34 pm-11:58 pm

1 stop7h 24m

$892

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 7/3

7:01 am-5:21 pm

2 stops10h 20m

Evansville Dress Regional

Sun 7/5

1:46 pm-6:42 pm

1 stop4h 56m

$1,273

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Wed 5/20

11:09 am-9:44 pm

2 stops10h 35m

Evansville Dress Regional

Sat 5/23

10:10 am-8:14 pm

2 stops10h 04m

$1,495

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 5/14

11:09 am-9:44 pm

2 stops10h 35m

Evansville Dress Regional

Sat 5/16

10:10 am-8:14 pm

2 stops10h 04m

$1,495

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 8/25

8:55 am-4:56 pm

2 stops8h 01m

Evansville Dress Regional

Fri 9/4

1:30 pm-8:24 pm

2 stops6h 54m

$1,495

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Wed 6/3

7:00 am-5:15 pm

2 stops10h 15m

Evansville Dress Regional

Wed 6/10

10:08 am-8:31 pm

2 stops10h 23m

$1,495

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 6/7

8:52 am-5:21 pm

2 stops8h 29m

Evansville Dress Regional

Sun 6/14

10:08 am-6:29 pm

2 stops8h 21m

$1,495

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Chicago to Evansville

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Evansville in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Evansville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Evansville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Evansville flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Evansville flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Evansville flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Evansville

Have a flexible travel schedule? Discover the best time to fly to Evansville from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest time of day to fly from CHI to EVV?

Find hourly flight availability from Chicago to Evansville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 34% on flights from Chicago to Evansville by exploring options for tickets in the morning.

Weekly flight availability from Chicago to Evansville

Explore weekly flight availability from Chicago to Evansville. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 24, 2026.

The most flights from CHI to EVV are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

Reviews of airlines servicing Evansville

Get insights into the airlines that provide service to Evansville. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Evansville. Reviews last updated April 24, 2026.
Read through reviews of airlines operating flights from Chicago to Evansville, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,666 reviews

Crew

7.9

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,666 reviews
American Airlines
7.1
Good
11,666 reviews

Crew

7.9

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Evansville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Evansville from Chicago?

    If you book a flight to Evansville from Chicago, you will be flying to Dress Regional, which is the city’s only airport. Evansville Dress Regional (EVV) is located 4.4 mi from the center of Evansville. There are 5 flights from Chicago to Dress Regional per day from 1 airline.

  • How long is the flight from Chicago to Evansville?

    Airlines like American Airlines fly from Chicago to Evansville in about 1h 24m. The time it takes to get you to your destination is usually consistent. The distance from Chicago to Evansville is about 273 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Chicago to Evansville round-trip?

    Currently priced at $311, American Airlines will fly you from Chicago to Evansville and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip.

  • What are the most reliable airlines from Chicago to Evansville?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Evansville on time: Envoy Air (61%), American Airlines (59%), Qantas Airways (56%).

  • Can I find deals for flights from Chicago to Evansville that include hotel bookings?

    Yes. In addition to deals on Chicago to Evansville flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Evansville?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Evansville.

  • Can I find deals for business class flights from Chicago to Evansville?

    Yes. Cheapflights offers flight deals from Chicago to Evansville by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Evansville?

Book flights to Evansville if you plan to visit one of these locations
Vincennes
Jasper

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Alternative routes for Chicago to Evansville

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Top airline flying from Chicago to Evansville

Discover the top airline that operate flights from Chicago to Evansville. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$311Average$578FlexibilityNo cancel feeOn-time71%

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