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$130+ Cheap flights from Evansville (EVV) to Chicago (CHI)

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Evansville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Evansville (EVV) to Chicago (CHI). 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 20, 2025.

Round-trip from

$369
(American Airlines)

One-way from

$130
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$397

Good round-trip deal

$456 or less

Good one-way deal

$273 or less
From Evansville Dress Regional to Chicago (CHI)
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One-way flight from Evansville Dress Regional to Chicago (CHI)
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Highest demand for flights based on searches. 22% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Evansville Dress Regional to Chicago (CHI).
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Price to beat on a one-way flight from Evansville Dress Regional to Chicago (CHI).
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Find flight deals from Evansville to Chicago

Cheapest flights from Evansville to Chicago
Explore the most affordable flight options available from Evansville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/19. 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.
Sat 9/207:01 amEVV - ORD
Nonstop1h 50mAmerican Airlines
Sun 9/214:15 pmORD - EVV
Nonstop1h 19mAmerican Airlines
Deal found 8/19$369
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Sat 9/201:56 pmEVV - ORD
1 stop6h 31mAmerican Airlines
Thu 10/27:02 amORD - EVV
1 stop5h 21mAmerican Airlines
Deal found 8/19$389
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/196:04 pmEVV - ORD
Nonstop1h 46mAmerican Airlines
Sun 9/2110:08 pmORD - EVV
Nonstop1h 21mAmerican Airlines
Deal found 8/19$407
This American Airlines deal was found by Cheapflights users on 8/18. 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 8/306:25 amEVV - ORD
Nonstop1h 44mAmerican Airlines
Mon 9/110:21 pmORD - EVV
Nonstop1h 22mAmerican Airlines
Deal found 8/18$424
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 10/317:00 amEVV - ORD
1 stop7h 12mAmerican Airlines
Sun 11/27:10 amORD - EVV
1 stop5h 21mAmerican Airlines
Deal found 8/19$427
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 8/228:58 pmEVV - ORD
2 stops38h 12mMultiple Airlines
Sun 8/316:10 amORD - EVV
1 stop12h 50mMultiple Airlines
Deal found 8/18$451
This American Airlines deal was found by Cheapflights users on 8/18. 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 11/207:00 amEVV - ORD
Nonstop1h 43mAmerican Airlines
Fri 11/215:15 pmORD - EVV
Nonstop1h 18mAmerican Airlines
Deal found 8/18$455
This American Airlines deal was found by Cheapflights users on 8/18. 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 8/216:30 amEVV - ORD
Nonstop1h 44mAmerican Airlines
Sun 8/2410:21 pmORD - EVV
Nonstop1h 22mAmerican Airlines
Deal found 8/18$457
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:13 amEVV - MDW
1 stop5h 13mDelta
Thu 10/210:35 amMDW - EVV
1 stop6h 46mDelta
Deal found 8/19$1,123
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:02 amEVV - MDW
2 stops6h 26mDelta
Sun 11/25:04 pmMDW - EVV
1 stop4h 49mDelta
Deal found 8/18$1,128
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:13 amEVV - MDW
2 stops8h 24mDelta
Mon 9/19:30 amMDW - EVV
2 stops6h 50mDelta
Deal found 8/18$1,139
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2410:13 amEVV - MDW
2 stops8h 24mDelta
Sat 8/301:08 pmMDW - EVV
2 stops8h 46mDelta
Deal found 8/20$1,145

Cheapflights Fare Finder

 
Customize your flight search to find flights from Evansville to Chicago 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 20, 2025.
Use the filters below to find and compare flights from Evansville to Chicago that are best for you.

Fly from

Evansville

Fly to

Chicago

Route

Depart

Return

Price

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 9/20

7:01 am-8:51 am

Nonstop1h 50m

Chicago O'Hare Intl

Sun 9/21

4:15 pm-5:34 pm

Nonstop1h 19m

$369

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 10/31

6:00 am-7:51 am

Nonstop1h 51m

Chicago O'Hare Intl

Sun 11/2

5:15 pm-6:33 pm

Nonstop1h 18m

$369

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 9/20

6:04 pm-7:50 pm

Nonstop1h 46m

Chicago O'Hare Intl

Thu 10/2

10:08 pm-11:29 pm

Nonstop1h 21m

$369

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 10/4

7:01 am-8:51 am

Nonstop1h 50m

Chicago O'Hare Intl

Sun 10/5

10:08 pm-11:29 pm

Nonstop1h 21m

$369

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Wed 10/1

6:23 am-11:48 am

1 stop5h 25m

Chicago Midway

Fri 10/3

12:43 pm-5:21 pm

1 stop4h 38m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 11/20

6:00 am-11:55 am

1 stop5h 55m

Chicago Midway

Fri 11/21

5:25 pm-10:03 pm

1 stop4h 38m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 9/8

5:00 pm-9:26 pm

1 stop4h 26m

Chicago Midway

Thu 9/11

12:43 pm-5:21 pm

1 stop4h 38m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 9/26

6:23 am-11:48 am

1 stop5h 25m

Chicago Midway

Sun 9/28

6:00 am-12:37 pm

1 stop6h 37m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 9/19

1:17 pm-5:35 pm

1 stop4h 18m

Chicago Midway

Sun 9/21

6:00 am-12:37 pm

1 stop6h 37m

$1,123

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 10/2

6:23 am-11:48 am

1 stop5h 25m

Chicago Midway

Fri 10/3

6:00 am-12:37 pm

1 stop6h 37m

$1,123

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 29 results
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Best time to book a flight from Evansville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Evansville 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 Evansville to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Evansville to Chicago (average of $245). Flying from Evansville to Chicago in March is currently the most expensive (average of $321). 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 EVV to CHI?

Find hourly flight availability from Evansville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

One of the essential ways to save on airfare from Evansville to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 30% on airfare.

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 20, 2025.
Read through reviews of airlines operating flights from Evansville to Chicago, 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

Food

6.5

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Food

6.5

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Evansville to Chicago. 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 from for flights from Evansville to Chicago?

    Located just 4.4 mi from the city center, Evansville Dress Regional is the airport most travelers will use when flying to Chicago from Evansville. Booking flights from Dress Regional (EVV) to Chicago should be relatively easy as there are 3 daily outbound flights to Chicago from 1 airline.

  • How long is the flight from Evansville to Chicago?

    A quick flight from Evansville to Chicago can take about 1h 50m. American Airlines provides one of the quickest options available for as low as $369. The distance between Evansville and Chicago is about 273 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $246. Users have found that American Airlines is 34% cheaper than the other options available to this destination.

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

    No one likes to see their flight delayed. When booking a flight from Evansville to Chicago consider choosing Qatar Airways (91%), Japan Airlines (85%) or American Airlines (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Evansville to Chicago?

    The cheapest flight price from Evansville to Chicago is $194. On average you can expect to pay $1,731. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $451.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Evansville to Chicago 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 Evansville to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Evansville to Chicago (average of $245). Flying from Evansville to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top airline flying from Evansville to Chicago

Discover the top airline that operate flights from Evansville to Chicago. 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$446FlexibilityNo cancel feeOn-time71%

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