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$105+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/105:35 pmEVV - ORD
2 stops26h 39mMultiple Airlines
Fri 11/146:48 amORD - EVV
1 stop10h 07mMultiple Airlines
Deal found 10/26$256
This Kiwi.com deal was found by Cheapflights users on 10/25. 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
2 stops17h 38mMultiple Airlines
Sun 12/712:09 pmORD - EVV
1 stop28h 46mMultiple Airlines
Deal found 10/25$294
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/43:27 pmEVV - ORD
1 stop21h 49mMultiple Airlines
Sun 12/218:09 pmORD - EVV
1 stop15h 33mMultiple Airlines
Deal found 10/26$297
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 stop20h 46mMultiple Airlines
Sun 12/1412:09 pmORD - EVV
1 stop28h 46mMultiple Airlines
Deal found 10/25$311
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/257:05 pmEVV - ORD
Nonstop1h 51mAmerican Airlines
Tue 12/210:30 pmORD - EVV
Nonstop1h 24mAmerican Airlines
Deal found 10/26$331
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 10/315:35 pmEVV - ORD
1 stop22h 48mMultiple Airlines
Sun 11/22:31 pmORD - EVV
2 stops26h 24mMultiple Airlines
Deal found 10/27$349
This KAYAK deal was found by Cheapflights users on 10/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/310:20 amEVV - MDW
1 stop5h 54mDelta
Thu 11/66:00 amMDW - EVV
1 stop6h 43mDelta
Deal found 10/27$1,083
This Delta deal was found by Cheapflights users on 10/25. 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 11/910:10 amEVV - MDW
2 stops7h 58mDelta
Thu 11/139:34 amMDW - EVV
2 stops7h 41mDelta
Deal found 10/25$1,230
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 11/610:20 amEVV - MDW
2 stops8h 05mDelta
Mon 11/101:15 pmMDW - EVV
2 stops8h 53mDelta
Deal found 10/26$1,239
This Delta deal was found by Cheapflights users on 10/26. 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 12/610:09 amEVV - MDW
2 stops7h 57mDelta
Sun 12/71:14 pmMDW - EVV
2 stops8h 33mDelta
Deal found 10/26$1,248
This Delta deal was found by Cheapflights users on 10/25. 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 11/86:02 amEVV - MDW
2 stops6h 24mDelta
Mon 11/109:34 amMDW - EVV
2 stops7h 41mDelta
Deal found 10/25$1,267
This Delta deal was found by Cheapflights users on 10/27. 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.
Mon 11/1010:10 amEVV - MDW
2 stops7h 58mDelta
Fri 11/141:15 pmMDW - EVV
2 stops8h 53mDelta
Deal found 10/27$1,274

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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$256
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$467

Good round-trip deal

$424 or less

Good one-way deal

$288 or less
Provider with most accurate pricing for Evansville Dress Regional-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Evansville Dress Regional-Chicago (CHI) flights.
Search Deals
From Evansville Dress Regional to Chicago (CHI)
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One-way flight from Evansville Dress Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Evansville Dress Regional to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Evansville Dress Regional to Chicago (CHI).
Search Deals

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 October 27, 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

Mon 11/10

5:35 pm-11:06 pm

1 stop29h 31m

Chicago O'Hare Intl

Fri 11/14

6:48 am-4:55 pm

1 stop10h 07m

$266

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 12/5

5:35 pm-11:13 am

2 stops17h 38m

Chicago O'Hare Intl

Sun 12/7

12:09 pm-4:55 pm

1 stop28h 46m

$294

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 12/4

3:27 pm-1:16 pm

1 stop21h 49m

Chicago O'Hare Intl

Sun 12/21

8:09 pm-11:42 am

1 stop15h 33m

$297

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 12/5

5:35 pm-2:21 pm

1 stop20h 46m

Chicago O'Hare Intl

Sun 12/14

12:09 pm-4:55 pm

1 stop28h 46m

$311

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Thu 1/1

5:10 am-12:40 pm

1 stop7h 30m

Chicago O'Hare Intl

Sat 1/3

8:03 am-3:22 pm

1 stop7h 19m

$356

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Tue 11/25

7:05 pm-8:56 pm

Nonstop1h 51m

Chicago O'Hare Intl

Tue 12/2

10:30 pm-11:54 pm

Nonstop1h 24m

$363

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 12/6

7:00 am-8:44 am

Nonstop1h 44m

Chicago O'Hare Intl

Sun 12/7

10:15 pm-11:39 pm

Nonstop1h 24m

$369

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Tue 3/3

6:00 am-8:50 am

2 stops26h 50m

Chicago Midway

Wed 3/4

1:00 pm-4:56 pm

2 stops27h 56m

$708

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 11/9

10:10 am-6:08 pm

2 stops7h 58m

Chicago Midway

Thu 11/13

9:34 am-5:15 pm

2 stops7h 41m

$1,230

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Thu 11/6

10:20 am-6:25 pm

2 stops8h 05m

Chicago Midway

Mon 11/10

1:15 pm-10:08 pm

2 stops8h 53m

$1,239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 20 results
1
2

Compare providers for flights from Evansville to Chicago

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 Evansville to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Evansville-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Evansville-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Evansville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Evansville-Chicago 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 Evansville-Chicago 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 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, January is the cheapest month in which you can book a flight from Evansville to Chicago (average of $73). Flying from Evansville to Chicago in July is currently the most expensive (average of $139). 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 October 27, 2025.

One of the essential ways to save on airfare from Evansville to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 43% 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 October 27, 2025.

The most flights from EVV to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 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 October 27, 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
11,033 reviews

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.4

Overall

7.2

Entertainment

6.9

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
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.4

Overall

7.2

Entertainment

6.9

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 26h 50m. Delta provides one of the quickest options available for as low as $708. The distance between Evansville and Chicago is about 259 mi.

  • 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 31% 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 (90%), Qatar Airways (85%) or American Airlines (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 $159. On average you can expect to pay $1,630. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $256.

  • 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, January is the cheapest month in which you can book a flight from Evansville to Chicago (average of $73). Flying from Evansville to Chicago in July is currently the most expensive (average of $139). 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
Porter
Benton Harbor

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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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$446FlexibilityNo cancel feeOn-time71%

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