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$156+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Cheap 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 May 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/187:53 am
EVV
-
ORD
1 stop28h 30m
Multiple Airlines
Wed 5/203:55 pm
ORD
-
EVV
1 stop27h 39m
Multiple Airlines
Deal found 4/30$293
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 6/36:50 am
EVV
-
ORD
Nonstop1h 49m
American Airlines
Sat 6/65:28 pm
ORD
-
EVV
Nonstop1h 26m
American Airlines
Deal found 4/30$385
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/1911:46 am
EVV
-
MDW
1 stop8h 47m
Allegiant Air
Fri 6/266:38 pm
MDW
-
EVV
2 stops38h 42m
Allegiant Air
Deal found 5/5$389
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 11/44:42 pm
EVV
-
ORD
1 stop7h 08m
Multiple Airlines
Tue 11/104:44 pm
ORD
-
EVV
1 stop23h 18m
Multiple Airlines
Deal found 5/4$399
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/2611:46 am
EVV
-
MDW
1 stop8h 47m
Allegiant Air
Sun 6/282:46 pm
MDW
-
EVV
2 stops28h 59m
Allegiant Air
Deal found 5/2$401
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/256:04 pm
EVV
-
ORD
Nonstop1h 46m
American Airlines
Tue 9/2910:00 pm
ORD
-
EVV
Nonstop1h 21m
American Airlines
Deal found 4/30$432
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2812:46 pm
EVV
-
ORD
1 stop7h 02m
American Airlines
Thu 6/411:00 pm
ORD
-
EVV
Nonstop1h 21m
American Airlines
Deal found 4/30$442
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/196:23 pm
EVV
-
ORD
Nonstop1h 50m
American Airlines
Sat 5/2310:40 pm
ORD
-
EVV
Nonstop1h 19m
American Airlines
Deal found 5/5$449
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/18:29 am
EVV
-
MDW
1 stop12h 11m
Allegiant Air
Sun 6/72:46 pm
MDW
-
EVV
2 stops29h 04m
Allegiant Air
Deal found 5/2$564
This Delta deal was found by Cheapflights users on 5/2. 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.
Wed 5/131:42 pm
EVV
-
MDW
1 stop26h 30m
Delta
Thu 5/216:23 am
MDW
-
EVV
1 stop27h 07m
Delta
Deal found 5/2$1,042
This Delta deal was found by Cheapflights users on 5/2. 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.
Wed 5/136:18 am
EVV
-
MDW
2 stops12h 15m
Delta
Wed 5/206:23 am
MDW
-
EVV
1 stop27h 07m
Delta
Deal found 5/2$1,047
This Delta deal was found by Cheapflights users on 5/1. 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 8/2110:05 am
EVV
-
MDW
2 stops8h 26m
Delta
Mon 8/249:30 am
MDW
-
EVV
2 stops7h 26m
Delta
Deal found 5/1$1,435

Find 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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$293
(Kiwi.com)

One-way from

$156
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$396

Good round-trip deal

$590 or less

Good one-way deal

$369 or less
Provider with most accurate pricing for Evansville Dress Regional-Chicago (CHI) flight deals.
Search Deals
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. 13% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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).
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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 May 5, 2026.
Use the filters below to find and compare flights from Evansville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 6/26

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Sun 6/28

2:46 pm-7:45 pm

2 stops28h 59m

$401

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 6/3

6:50 am-8:39 am

Nonstop1h 49m

Chicago O'Hare Intl

Sat 6/6

9:30 am-4:08 pm

1 stop6h 38m

$415

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 9/25

6:04 pm-7:50 pm

Nonstop1h 46m

Chicago O'Hare Intl

Tue 9/29

7:02 am-12:06 pm

1 stop5h 04m

$442

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 6/26

6:39 pm-8:40 pm

Nonstop2h 01m

Chicago O'Hare Intl

Sun 6/28

11:00 pm-12:21 am

Nonstop1h 21m

$499
Quickest round-trip

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 9/23

6:04 pm-7:50 pm

Nonstop1h 46m

Chicago O'Hare Intl

Sat 9/26

4:40 pm-5:53 pm

Nonstop1h 13m

$536

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 6/10

12:46 pm-5:42 pm

1 stop4h 56m

Chicago O'Hare Intl

Fri 6/12

11:00 pm-12:21 am

Nonstop1h 21m

$815

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 6/3

1:42 pm-8:14 pm

2 stops6h 32m

Chicago O'Hare Intl

Sat 6/6

11:09 am-9:44 pm

2 stops10h 35m

$1,435

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Wed 9/30

6:00 am-4:36 pm

2 stops10h 36m

Chicago O'Hare Intl

Fri 10/2

8:55 am-4:56 pm

2 stops8h 01m

$1,435

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 9/25

10:05 am-4:36 pm

2 stops6h 31m

Chicago O'Hare Intl

Tue 9/29

1:35 pm-10:03 pm

2 stops8h 28m

$1,435

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sun 11/1

1:30 pm-8:24 pm

2 stops6h 54m

Chicago O'Hare Intl

Tue 11/10

8:55 am-4:54 pm

2 stops7h 59m

$1,435

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 28 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Evansville-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 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 May 5, 2026.

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 57% 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 May 5, 2026.

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

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 May 5, 2026.
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
7.1
Good
11,667 reviews

Comfort

7.2

Boarding

7.5

Overall

7.1

Food

6.4

Entertainment

6.9

Crew

7.9

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
7.1
Good
11,667 reviews
American Airlines
7.1
Good
11,667 reviews

Comfort

7.2

Boarding

7.5

Overall

7.1

Food

6.4

Entertainment

6.9

Crew

7.9

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 2 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 49m. Allegiant Air provides one of the quickest options available for as low as $415. 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 $331. Users have found that American Airlines is 19% 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 Envoy Air (79%), Japan Airlines (69%) or American Airlines (68%) 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 $367. On average you can expect to pay $1,017. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $405.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$331Average$444FlexibilityNo cancel feeOn-time71%

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