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Evansville

$126+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EVV
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$369
(American Airlines)

One-way from

$126
(Kiwi.com)
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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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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/17. 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 10/1810:08 pmORD - EVV
Nonstop1h 24mAmerican Airlines
Sun 10/195:21 pmEVV - ORD
Nonstop1h 44mAmerican Airlines
Deal found 9/17$369
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/86:58 pmORD - EVV
1 stop14h 37mMultiple Airlines
Fri 10/105:35 pmEVV - ORD
1 stop22h 04mMultiple Airlines
Deal found 9/15$384
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/304:15 pmORD - EVV
Nonstop1h 19mAmerican Airlines
Sat 10/46:04 pmEVV - ORD
Nonstop1h 46mAmerican Airlines
Deal found 9/15$385
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/315:20 amORD - EVV
1 stop6h 18mAmerican Airlines
Sun 11/25:10 amEVV - ORD
1 stop7h 45mAmerican Airlines
Deal found 9/17$389
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/95:50 amORD - EVV
1 stop13h 37mMultiple Airlines
Fri 10/105:35 pmEVV - ORD
1 stop22h 04mMultiple Airlines
Deal found 9/15$391
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/173:37 pmORD - EVV
Nonstop1h 14mAmerican Airlines
Fri 10/246:03 amEVV - ORD
Nonstop1h 51mAmerican Airlines
Deal found 9/17$407

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 September 17, 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

Sat 10/18

10:08 pm-11:32 pm

Nonstop1h 24m

Evansville Dress Regional

Sun 10/19

5:21 pm-7:05 pm

Nonstop1h 44m

$369

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 10/31

3:37 pm-4:51 pm

Nonstop1h 14m

Evansville Dress Regional

Sun 11/2

7:05 pm-8:56 pm

Nonstop1h 51m

$369

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Wed 10/8

6:58 pm-9:35 am

1 stop14h 37m

Evansville Dress Regional

Fri 10/10

5:35 pm-3:39 pm

1 stop22h 04m

$384

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Tue 9/30

4:15 pm-5:34 pm

Nonstop1h 19m

Evansville Dress Regional

Sat 10/4

6:04 pm-7:50 pm

Nonstop1h 46m

$385

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 10/9

5:50 am-7:27 pm

1 stop13h 37m

Evansville Dress Regional

Fri 10/10

5:35 pm-3:39 pm

1 stop22h 04m

$391

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Fri 11/14

6:05 am-4:55 pm

1 stop10h 50m

$136

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 9/25

6:10 am-11:42 am

2 stops29h 32m

$147

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 11/13

4:01 pm-4:55 pm

2 stops24h 54m

$155

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Sun 10/19

1:26 pm-4:55 pm

2 stops27h 29m

$172

ChicagoEvansville

ORD - EVV

ORDEVV

Chicago O'Hare Intl

Thu 12/11

2:47 pm-4:55 pm

2 stops26h 08m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 13 results
1
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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, August is the cheapest month in which you can book a flight from Chicago to Evansville (average of $449). Flying from Chicago to Evansville in November is currently the most expensive (average of $579). 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 September 17, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 20% on flights from Chicago to Evansville by exploring options for tickets at noon.

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 September 17, 2025.

The most flights from CHI to EVV are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 September 17, 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
10,000 reviews

Comfort

7.2

Crew

8.0

Food

6.4

Overall

7.2

Entertainment

6.9

Boarding

7.5

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Crew

8.0

Food

6.4

Overall

7.2

Entertainment

6.9

Boarding

7.5

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 6 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.

  • 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: Qantas Airways (76%), American Airlines (74%), Envoy Air (74%).

  • 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, August is the cheapest month in which you can book a flight from Chicago to Evansville (average of $449). Flying from Chicago to Evansville in November is currently the most expensive (average of $579). 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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Alternative routes for Chicago to Evansville

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$375FlexibilityNo cancel feeOn-time71%

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