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$151+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$261
(American Airlines)

One-way from

$151
(American Airlines)

Popular in

October

Cheapest in

May

Average price

$179

Good round-trip deal

$497 or less

Good one-way deal

$268 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.
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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. 19% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 5/132:51 pmEVV - ORD
Nonstop1h 42mAmerican Airlines
Thu 5/158:50 pmORD - EVV
Nonstop1h 18mAmerican Airlines
Deal found 4/29$261
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/158:41 pmEVV - ORD
2 stops18h 52mMultiple Airlines
Sun 6/225:15 amORD - EVV
3 stops34h 34mMultiple Airlines
Deal found 4/30$435
This Delta deal was found by Cheapflights users on 4/28. 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 8/2810:05 amEVV - MDW
1 stop11h 42mDelta
Tue 9/26:00 amMDW - EVV
1 stop10h 57mDelta
Deal found 4/28$465
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/189:26 amEVV - ORD
2 stops9h 11mDelta
Sun 5/255:30 amORD - EVV
1 stop7h 08mDelta
Deal found 4/30$1,090

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 1, 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

Tue 5/13

2:51 pm-4:33 pm

Nonstop1h 42m

Chicago O'Hare Intl

Thu 5/15

8:50 pm-10:08 pm

Nonstop1h 18m

$261

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sun 6/15

8:41 pm-3:33 pm

2 stops18h 52m

Chicago O'Hare Intl

Sun 6/22

5:15 am-3:49 pm

3 stops34h 34m

$435

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sun 6/15

6:00 am-6:02 pm

1 stop12h 02m

Chicago Midway

Sun 6/22

4:26 pm-5:19 pm

1 stop24h 53m

$465

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sun 5/18

9:26 am-6:37 pm

2 stops9h 11m

Chicago O'Hare Intl

Sun 5/25

5:30 am-12:38 pm

1 stop7h 08m

$1,090

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 5/16

2:51 pm-4:33 pm

Nonstop1h 42m

$151

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Mon 6/16

4:39 pm-10:50 am

2 stops18h 11m

$176

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 5/31

1:18 pm-8:29 am

1 stop19h 11m

$210

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Mon 6/16

6:04 am-11:59 am

1 stop5h 55m

$582

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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*2 stars
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 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 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, 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 May 1, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 1, 2025.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 are the cheapest airlines flying from Evansville to Chicago round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $261. Another option worth looking into is Delta, starting at $465 round trip. Users have found that American Airlines is 32% 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 (80%), Air Wisconsin (80%) or Qatar Airways (77%) 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 $143. On average you can expect to pay $529. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $364.

  • 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 Evansville?

Book flights to Evansville if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$431FlexibilityNo cancel feeOn-time71%

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