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Evansville

$129+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EVV
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$246
(Kiwi.com)

One-way from

$129
(Kiwi.com)

Popular in

September

Cheapest in

October

Average price

$704

Good one-way deal

$385 or less
Provider with most accurate pricing for Chicago (CHI)-Evansville Dress Regional flight deals.
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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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Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a one-way flight from Chicago (CHI) to Evansville Dress Regional.
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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 January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 1/1210:48 amORD - EVV
1 stop8h 18mMultiple Airlines
Fri 1/307:46 pmEVV - ORD
1 stop20h 54mMultiple Airlines
Deal found 1/7$358
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Mon 6/1510:31 pmORD - EVV
Nonstop1h 25mAmerican Airlines
Tue 6/236:23 pmEVV - ORD
Nonstop1h 52mAmerican Airlines
Deal found 1/8$362
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/75:30 pmORD - EVV
Nonstop1h 21mAmerican Airlines
Sun 2/87:10 amEVV - ORD
Nonstop1h 51mAmerican Airlines
Deal found 1/7$364
This American Airlines deal was found by Cheapflights users on 1/7. 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 3/1710:29 pmORD - EVV
Nonstop1h 17mAmerican Airlines
Tue 3/244:22 pmEVV - ORD
Nonstop1h 43mAmerican Airlines
Deal found 1/7$385
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/62:55 pmORD - EVV
Nonstop1h 23mAmerican Airlines
Sun 2/87:10 amEVV - ORD
Nonstop1h 51mAmerican Airlines
Deal found 1/7$399
This American Airlines deal was found by Cheapflights users on 1/7. 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 3/172:58 pmORD - EVV
1 stop8h 19mAmerican Airlines
Sat 3/216:55 pmEVV - ORD
1 stop5h 03mAmerican Airlines
Deal found 1/7$405

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 January 8, 2026.
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 2/6

10:48 am-7:06 pm

1 stop8h 18m

Evansville Dress Regional

Sun 2/8

7:10 pm-6:29 pm

2 stops23h 19m

$246

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Mon 6/15

10:31 pm-11:56 pm

Nonstop1h 25m

Evansville Dress Regional

Tue 6/23

6:23 pm-8:15 pm

Nonstop1h 52m

$362

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sat 2/7

5:30 pm-6:51 pm

Nonstop1h 21m

Evansville Dress Regional

Sun 2/8

3:30 pm-9:27 pm

1 stop5h 57m

$374

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 3/17

10:29 pm-11:46 pm

Nonstop1h 17m

Evansville Dress Regional

Sat 3/21

4:22 pm-6:05 pm

Nonstop1h 43m

$385

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Wed 3/18

10:29 pm-11:46 pm

Nonstop1h 17m

Evansville Dress Regional

Tue 3/24

4:22 pm-6:05 pm

Nonstop1h 43m

$385

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 3/17

5:00 am-11:29 am

1 stop6h 29m

Evansville Dress Regional

Tue 3/24

4:22 pm-6:05 pm

Nonstop1h 43m

$395

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 2/6

7:35 pm-8:58 pm

Nonstop1h 23m

Evansville Dress Regional

Sun 2/8

4:51 pm-6:45 pm

Nonstop1h 54m

$399

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 1/22

8:43 pm-7:06 pm

2 stops22h 23m

$132

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 2/5

5:32 pm-7:06 pm

2 stops25h 34m

$133

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 3/8

4:18 pm-7:06 pm

1 stop26h 48m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 17 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 January.
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, December is the cheapest month in which you can book a flight from Chicago to Evansville (average of $98). Flying from Chicago to Evansville in May is currently the most expensive (average of $148). 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 January 8, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 52% on flights from Chicago to Evansville by exploring options for tickets at noon.

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 January 8, 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
7.2
Good
11,094 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,094 reviews
American Airlines
7.2
Good
11,094 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 25m. 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 59% 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: Japan Airlines (72%), Qantas Airways (71%), American Airlines (63%).

  • What are the cheapest flights from Chicago to Evansville?

    Looking at all options, your cheapest flight can be booked for $385. While the most popular route (Chicago O'Hare Intl - Evansville Dress Regional) can be booked for $365 on average, our data indicates $385 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.

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

    Currently, December is the cheapest month in which you can book a flight from Chicago to Evansville (average of $98). Flying from Chicago to Evansville in May is currently the most expensive (average of $148). 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$364FlexibilityNo cancel feeOn-time71%

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