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$109+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$234
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$358

Good round-trip deal

$406 or less

Good one-way deal

$379 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 September 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 September 17, 2025.

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 11/1312:53 pmEVV - ORD
1 stop24h 45mMultiple Airlines
Thu 11/206:05 amORD - EVV
1 stop13h 12mMultiple Airlines
Deal found 9/15$234
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.
Sun 11/1612:53 pmEVV - ORD
1 stop24h 45mMultiple Airlines
Thu 11/206:05 amORD - EVV
1 stop13h 12mMultiple Airlines
Deal found 9/15$239
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/275:35 pmEVV - ORD
1 stop22h 48mMultiple Airlines
Tue 10/287:43 pmORD - EVV
2 stops36h 08mMultiple Airlines
Deal found 9/16$259
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/1312:53 pmEVV - ORD
1 stop24h 45mMultiple Airlines
Wed 11/195:59 pmORD - EVV
2 stops25h 18mMultiple Airlines
Deal found 9/16$261
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:35 pmEVV - ORD
1 stop24h 18mMultiple Airlines
Thu 10/236:58 pmORD - EVV
1 stop21h 57mMultiple Airlines
Deal found 9/17$267
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.
Fri 11/145:35 pmEVV - ORD
1 stop27h 48mMultiple Airlines
Thu 11/206:05 amORD - EVV
1 stop13h 12mMultiple Airlines
Deal found 9/15$269
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.
Sun 11/1612:53 pmEVV - MDW
1 stop11h 37mMultiple Airlines
Thu 11/204:00 pmMDW - EVV
2 stops22h 12mMultiple Airlines
Deal found 9/15$275
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/145:35 pmEVV - ORD
1 stop23h 29mMultiple Airlines
Wed 11/195:59 pmORD - EVV
2 stops25h 18mMultiple Airlines
Deal found 9/16$291
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.
Fri 12/55:35 pmEVV - ORD
1 stop25h 09mMultiple Airlines
Mon 12/86:05 amORD - EVV
1 stop10h 50mMultiple Airlines
Deal found 9/15$296
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.
Sun 11/1612:53 pmEVV - MDW
1 stop11h 37mMultiple Airlines
Mon 11/179:27 amMDW - EVV
1 stop7h 28mMultiple Airlines
Deal found 9/15$321
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.
Fri 11/145:35 pmEVV - MDW
1 stop16h 51mMultiple Airlines
Thu 11/204:00 pmMDW - EVV
2 stops22h 12mMultiple Airlines
Deal found 9/15$328
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.
Fri 11/145:35 pmEVV - MDW
1 stop16h 51mMultiple Airlines
Mon 11/179:27 amMDW - EVV
1 stop7h 28mMultiple Airlines
Deal found 9/15$369

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 September 17, 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

Thu 11/13

12:53 pm-1:38 pm

1 stop24h 45m

Chicago O'Hare Intl

Thu 11/20

6:05 am-7:17 pm

1 stop13h 12m

$239

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Mon 10/20

5:35 pm-5:53 pm

1 stop24h 18m

Chicago O'Hare Intl

Thu 10/23

6:58 pm-4:55 pm

1 stop21h 57m

$267

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 11/14

5:35 pm-5:04 pm

1 stop23h 29m

Chicago O'Hare Intl

Thu 11/20

6:05 am-7:17 pm

1 stop13h 12m

$269

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sun 11/16

12:53 pm-1:38 pm

1 stop24h 45m

Chicago O'Hare Intl

Thu 11/20

6:05 am-7:17 pm

1 stop13h 12m

$277

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 11/14

5:35 pm-5:04 pm

1 stop23h 29m

Chicago O'Hare Intl

Wed 11/19

5:59 pm-7:17 pm

2 stops25h 18m

$291

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 11/16

12:53 pm-12:30 am

1 stop11h 37m

Chicago Midway

Mon 11/17

9:27 am-4:55 pm

1 stop7h 28m

$321

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 11/8

5:10 am-12:26 pm

1 stop7h 16m

Chicago O'Hare Intl

Tue 11/11

3:44 pm-10:51 pm

1 stop7h 07m

$351

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 11/14

7:05 pm-8:56 pm

Nonstop1h 51m

Chicago O'Hare Intl

Wed 11/19

5:26 pm-6:45 pm

Nonstop1h 19m

$369

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 11/14

5:35 pm-10:26 am

1 stop16h 51m

Chicago Midway

Mon 11/17

9:27 am-4:55 pm

1 stop7h 28m

$369

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 11/13

8:19 am-11:55 pm

2 stops15h 36m

Chicago Midway

Mon 11/17

9:27 am-4:55 pm

1 stop7h 28m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 22 results
1
2
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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 September 17, 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 33% on airfare.

Weekly flight availability from Evansville to Chicago

Explore weekly flight availability from Evansville to Chicago. 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 EVV to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 September 17, 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

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

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

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

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.

  • 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 Japan Airlines (87%), American Airlines (80%) or Envoy Air (80%) 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 $278. On average you can expect to pay $1,819. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $259.

  • 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$444FlexibilityNo cancel feeOn-time71%

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