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Evansville

$149+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EVV
Sep 6 — Sep 131
Sun 9/6
Sun 9/13
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 August 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:59 pm -
1 stop15h 16m
Sun 8/303:46 pm -
2 stops28h 13m
Deal found 8/2$279
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/510:35 pm -
Nonstop1h 24m
Sun 9/66:25 pm -
Nonstop2h 05m
Deal found 8/2$415
This American Airlines deal was found by Cheapflights users on 8/2. 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.
Wed 11/2510:37 pm -
Nonstop1h 31m
Sun 11/296:40 am -
Nonstop2h 01m
Deal found 8/2$462
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/196:45 am -
1 stop6h 14m
Sat 9/264:53 pm -
Nonstop1h 59m
Deal found 8/5$484
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Sat 8/83:59 pm -
Nonstop1h 21m
Sun 8/96:00 am -
Nonstop2h 01m
Deal found 8/3$506
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/103:00 pm -
Nonstop1h 23m
Thu 9/174:53 pm -
Nonstop1h 59m
Deal found 8/6$509

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 August 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(Kiwi.com)

One-way from

$149
(Kiwi.com)

Good round-trip deal

$743 or less
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.
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From Chicago (CHI) to Evansville Dress Regional
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One-way flight from Chicago (CHI) to Evansville Dress Regional
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Price to beat on a round-trip flight from Chicago (CHI) to Evansville Dress Regional.
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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 August 7, 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 Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Fri 9/4

12:44 am-3:49 pm

2 stops15h 05m

Evansville Dress Regional

Sat 9/12

4:42 pm-10:59 pm

1 stop30h 17m

$417

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Sat 9/5

6:49 am-12:21 pm

1 stop5h 32m

Evansville Dress Regional

Sat 9/12

8:48 am-10:43 am

Nonstop1h 55m

$482

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Sat 9/19

6:45 am-12:59 pm

1 stop6h 14m

Evansville Dress Regional

Sat 9/26

4:53 pm-6:52 pm

Nonstop1h 59m

$484

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Sat 9/5

4:57 pm-11:27 pm

1 stop6h 30m

Evansville Dress Regional

Sun 9/6

6:25 pm-8:30 pm

Nonstop2h 05m

$485
Quickest round-trip

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Thu 9/10

3:00 pm-4:23 pm

Nonstop1h 23m

Evansville Dress Regional

Thu 9/17

4:53 pm-6:52 pm

Nonstop1h 59m

$509

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Tue 9/15

3:00 pm-4:23 pm

Nonstop1h 23m

Evansville Dress Regional

Thu 9/17

4:53 pm-6:52 pm

Nonstop1h 59m

$815

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Thu 10/8

5:00 am-12:20 pm

1 stop7h 20m

Evansville Dress Regional

Thu 10/8

4:38 pm-12:08 am

1 stop7h 30m

$933

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Sat 9/5

11:22 am-8:48 pm

2 stops9h 26m

Evansville Dress Regional

Sun 9/6

3:16 pm-8:55 pm

1 stop5h 39m

$1,031
Cheapest one-way

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Sat 9/5

6:30 pm-2:21 pm

1 stop19h 51m

$240

ChicagoEvansville

ORD Chicago O'Hare Intl - EVV Evansville Dress Regional

ORDEVV

Chicago O'Hare Intl

Sat 10/31

10:35 am-10:27 am

1 stop23h 52m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Showing 1-10 of 15 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 August.
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 August 7, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 44% 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 August 7, 2026.

The most flights from CHI to EVV are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 August 7, 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
11,883 reviews

Entertainment

6.8

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

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
11,883 reviews
American Airlines
7.1
Good
11,883 reviews

Entertainment

6.8

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

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 5h 32m. The time it takes to get you to your destination can typically vary by up to . The distance from Chicago to Evansville is about 273 mi.

  • 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: Japan Airlines (78%), American Airlines (72%), Envoy Air (72%).

  • What are the cheapest flights from Chicago to Evansville?

    Looking at all options, your cheapest flight can be booked for $415. While the most popular route (Chicago O'Hare Intl - Evansville Dress Regional) can be booked for $318 on average, our data indicates $785 when flying from Chicago to Evansville.

  • 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
Jasper
Vincennes

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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 August 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$422Average$771FlexibilityNo cancel feeOn-time71%

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