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Evansville

$119+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EVV
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Find 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 November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/146:48 amORD - EVV
1 stop10h 07mMultiple Airlines
Sun 11/1612:53 pmEVV - ORD
2 stops21h 48mMultiple Airlines
Deal found 11/3$281
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 12/610:15 pmORD - EVV
Nonstop1h 24mAmerican Airlines
Sun 12/76:03 pmEVV - ORD
Nonstop1h 47mAmerican Airlines
Deal found 11/2$368
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Fri 12/510:15 pmORD - EVV
Nonstop1h 24mAmerican Airlines
Tue 12/97:00 amEVV - ORD
Nonstop1h 44mAmerican Airlines
Deal found 11/2$369
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/144:08 pmORD - EVV
Nonstop1h 25mAmerican Airlines
Wed 1/147:13 amEVV - ORD
Nonstop1h 51mAmerican Airlines
Deal found 11/2$371
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 11/185:36 pmORD - EVV
Nonstop1h 17mAmerican Airlines
Sat 11/227:00 amEVV - ORD
Nonstop1h 43mAmerican Airlines
Deal found 11/3$415

Cheap 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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$264
(Kiwi.com)

One-way from

$119
(Kiwi.com)

Popular in

September

Cheapest in

May

Average price

$331
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
Highest demand for flights based on searches. 27% potential increase in price ($168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 4, 2025.
Use the filters below to find and compare flights from Chicago to Evansville that are best for you.

Fly from

Chicago

Fly to

Evansville

Route

Depart

Return

Price

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 11/14

6:48 am-4:55 pm

1 stop10h 07m

Evansville Dress Regional

Sun 11/16

12:53 pm-10:41 am

2 stops21h 48m

$281

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sat 12/6

10:15 pm-11:39 pm

Nonstop1h 24m

Evansville Dress Regional

Sun 12/7

6:03 pm-7:50 pm

Nonstop1h 47m

$368

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sat 12/20

10:15 pm-11:37 pm

Nonstop1h 22m

Evansville Dress Regional

Sun 1/4

7:00 am-8:41 am

Nonstop1h 41m

$369

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 12/5

10:15 pm-11:39 pm

Nonstop1h 24m

Evansville Dress Regional

Tue 12/9

7:00 am-8:44 am

Nonstop1h 44m

$369

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 12/14

5:34 pm-11:58 pm

1 stop6h 24m

Evansville Dress Regional

Wed 1/14

4:51 pm-6:45 pm

Nonstop1h 54m

$381

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 11/18

5:36 pm-6:53 pm

Nonstop1h 17m

Evansville Dress Regional

Sat 11/22

7:00 am-8:43 am

Nonstop1h 43m

$415

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 1/29

7:51 pm-7:06 pm

2 stops23h 15m

$125

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Mon 12/1

6:48 am-4:55 pm

1 stop10h 07m

$131

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 1/4

12:09 pm-11:42 am

1 stop23h 33m

$166

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 11/30

7:09 pm-4:55 pm

1 stop21h 46m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 15 results
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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Evansville flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 month to book a flight from Chicago to Evansville?

Currently, October is the cheapest month in which you can book a flight from Chicago to Evansville (average of $95). Flying from Chicago to Evansville in February is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 November 4, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 44% on flights from Chicago to Evansville by exploring options for tickets at noon.

How much does it cost to fly round-trip from Chicago to Evansville?

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 November 4, 2025.
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
7.2
Good
11,038 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 2 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 $191, 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. You may be able to fly from Chicago to Evansville for 56% less than the average price by searching for this airline.

  • 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: British Airways (100%), American Airlines (91%), Envoy Air (91%).

  • 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.

  • What is the cheapest month to book a flight from Chicago to Evansville?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Evansville (average of $95). Flying from Chicago to Evansville in February is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$364FlexibilityNo cancel feeOn-time71%

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