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$300+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$331
(American Airlines)

One-way from

$300
(Mytrip)

Popular in

October

Cheapest in

May

Good round-trip deal

$444 or less

Good one-way deal

$278 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. 18% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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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 junio 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
sáb. 7/196:45 amEVV - ORD
Nonstop1h 36mAmerican Airlines
mar. 8/123:27 pmORD - EVV
Nonstop1h 14mAmerican Airlines
Deal found 6/11$331
This Mytrip deal was found by Cheapflights users on 6/11. 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.
jue. 6/262:04 pmEVV - MDW
2 stops23h 59mAllegiant Air
lun. 6/309:12 amMDW - EVV
1 stop6h 37mAllegiant Air
Deal found 6/11$341
This Mytrip deal was found by Cheapflights users on 6/12. 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.
vie. 6/274:39 pmEVV - ORD
2 stops18h 11mMultiple Airlines
lun. 6/307:56 amORD - EVV
1 stop23h 38mMultiple Airlines
Deal found 6/12$383
This Delta deal was found by Cheapflights users on 6/10. 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.
jue. 8/216:10 amEVV - ORD
2 stops6h 35mDelta
dom. 8/242:00 pmORD - EVV
2 stops7h 54mDelta
Deal found 6/10$1,214
This Delta deal was found by Cheapflights users on 6/12. 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.
vie. 6/2710:23 amEVV - MDW
2 stops8h 18mDelta
mar. 7/11:09 pmMDW - EVV
2 stops8h 47mDelta
Deal found 6/12$1,214

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 junio 12, 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

sáb. 7/19

6:45 am-8:21 am

Nonstop1h 36m

Chicago O'Hare Intl

mar. 8/12

3:27 pm-4:41 pm

Nonstop1h 14m

$331

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

jue. 6/26

2:04 pm-2:03 pm

2 stops23h 59m

Chicago Midway

lun. 6/30

9:12 am-3:49 pm

1 stop6h 37m

$341

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

vie. 6/27

4:39 pm-10:50 am

2 stops18h 11m

Chicago O'Hare Intl

lun. 6/30

7:56 am-7:34 am

1 stop23h 38m

$383

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

jue. 8/21

6:10 am-12:45 pm

2 stops6h 35m

Chicago O'Hare Intl

dom. 8/24

2:00 pm-9:54 pm

2 stops7h 54m

$1,214

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

vie. 6/27

10:23 am-6:41 pm

2 stops8h 18m

Chicago Midway

mar. 7/1

1:09 pm-9:56 pm

2 stops8h 47m

$1,214

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

jue. 6/19

1:59 pm-3:33 pm

2 stops25h 34m

$300

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

dom. 6/22

2:04 pm-2:03 pm

2 stops23h 59m

$316

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

mié. 6/18

7:00 am-8:38 am

Nonstop1h 38m

$340

EvansvilleChicago

EVV - ORD

EVVORD

Evansville Dress Regional

sáb. 6/21

6:04 am-4:23 pm

2 stops10h 19m

$613

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

dom. 6/22

1:25 pm-6:02 pm

1 stop4h 37m

$741

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 junio 12, 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 31% 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 junio 12, 2025.

The most flights from EVV to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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 junio 12, 2025.
Read through reviews of airlines operating flights from Evansville to Chicago, such as Delta, Allegiant Air and American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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!
Allegiant Air
7.3
Good
725 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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 are 4 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 $331. Additional round-trip tickets that might be worth considering are offered by Allegiant Air and Delta, with the lowest prices starting at $341 and $1,214, respectively. Users have found that American Airlines is 16% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Evansville to Chicago one-way?

    $316 is the cheapest one-way deal found within the past few days, from Allegiant Air. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $340 and $613, respectively.

  • 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 British Airways (87%), Japan Airlines (82%) or Qatar Airways (75%) 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 $269. On average you can expect to pay $2,503. The most popular route, (Evansville Dress Regional - Chicago O'Hare Intl), can usually be booked for $369.

  • 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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Alternative routes for Evansville to Chicago

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$351Average$431FlexibilityNo cancel feeOn-time71%

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