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$180+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$369
(American Airlines)

One-way from

$180
(Mytrip)

Popular in

October

Cheapest in

June

Average price

$397

Good round-trip deal

$442 or less

Good one-way deal

$359 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. 21% potential increase in price ($105 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:45 amEVV - ORD
Nonstop1h 36mAmerican Airlines
Tue 7/810:04 pmORD - EVV
Nonstop1h 20mAmerican Airlines
Deal found 7/1$358
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/114:39 pmEVV - ORD
2 stops21h 34mMultiple Airlines
Thu 8/1410:12 amORD - EVV
3 stops29h 37mMultiple Airlines
Deal found 7/2$418
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 8/21:22 pmEVV - ORD
2 stops6h 53mDelta
Sun 8/39:00 amORD - EVV
2 stops8h 01mDelta
Deal found 7/2$1,016
This Delta deal was found by Cheapflights users on 7/3. 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 8/29:37 amEVV - MDW
2 stops9h 03mDelta
Mon 8/41:09 pmMDW - EVV
2 stops8h 43mDelta
Deal found 7/3$1,016

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 July 3, 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 8/2

6:45 am-8:21 am

Nonstop1h 36m

Chicago O'Hare Intl

Mon 8/4

10:04 pm-11:24 pm

Nonstop1h 20m

$369

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Mon 8/11

4:39 pm-2:13 pm

2 stops21h 34m

Chicago O'Hare Intl

Thu 8/14

10:12 am-3:49 pm

3 stops29h 37m

$418

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Sat 8/2

1:22 pm-8:15 pm

2 stops6h 53m

Chicago O'Hare Intl

Sun 8/3

9:00 am-5:01 pm

2 stops8h 01m

$1,016

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Sat 8/2

9:37 am-6:40 pm

2 stops9h 03m

Chicago Midway

Mon 8/4

1:09 pm-9:52 pm

2 stops8h 43m

$1,016

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 8/8

4:39 pm-2:13 pm

2 stops21h 34m

$180

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 8/8

6:00 am-7:44 am

Nonstop1h 44m

$228

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

Fri 9/12

10:14 am-6:04 pm

2 stops7h 50m

$508

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 8/8

10:23 am-6:40 pm

2 stops8h 17m

$508

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 July 3, 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.

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 July 3, 2025.
Read through reviews of airlines operating flights from Evansville to Chicago, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 is 1 daily outbound flight 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 $369. Another option worth looking into is Delta, starting at $1,016 round trip. Users have found that American Airlines is 2% 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 (95%), Piedmont Airlines (93%) or American Airlines (87%) 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 $336. On average you can expect to pay $444. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $407.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$361Average$431FlexibilityNo cancel feeOn-time71%

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