$185+ Cheap flights from Evansville (EVV) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — CHI
Dec 3 — Dec 101
Round-trip
1 adult, Economy
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Find cheap flights from Evansville to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Evansville to Chicago
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Best
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Cheapest flights from Evansville to ChicagoExplore 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 November 3, 2026.
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 November 3, 2026.
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/26:37 am -
Nonstop2h 03m
Tue 12/82:15 pm -
Nonstop1h 23m
Deal found 11/1![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:08 pm -
Nonstop1h 51m
Sun 12/62:15 pm -
Nonstop1h 23m
Deal found 11/2![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 11/114:15 pm -
Nonstop1h 49m
Wed 11/1810:37 pm -
Nonstop1h 22m
Deal found 11/1![American Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:42 pm -
1 stop8h 17m
Tue 12/84:00 pm -
2 stops24h 02m
Deal found 11/1![Multiple Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:37 am -
Nonstop2h 04m
Sat 11/2811:05 pm -
Nonstop1h 27m
Deal found 11/3![American Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 12/54:42 pm -
1 stop8h 26m
Sun 12/610:29 pm -
2 stops21h 07m
Deal found 11/2![Multiple Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:15 pm -
Nonstop1h 49m
Tue 11/1010:37 pm -
Nonstop1h 22m
Deal found 11/2![American Airlines logo]()
$421
Best flights from Evansville to ChicagoDiscover carefully curated flight deals from Evansville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2026.
Discover carefully curated flight deals from Evansville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2026.
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Tue 3/237:05 am -
Nonstop1h 55m
Wed 3/3110:30 pm -
Nonstop1h 29m
Deal found 11/1![American Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 12/54:42 pm -
1 stop8h 26m
Sun 12/610:37 pm -
2 stops20h 59m
Deal found 10/30![Multiple Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 12/54:08 pm -
Nonstop1h 51m
Sun 12/66:00 am -
1 stop5h 45m
Deal found 10/30![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 10/31. 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 11/244:47 pm -
1 stop7h 12m
Sat 11/286:41 am -
1 stop5h 33m
Deal found 10/31![American Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 10/31. 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 11/2010:11 am -
2 stops8h 19m
Fri 11/275:50 pm -
1 stop4h 32m
Deal found 10/31![Delta logo]()
$1,270
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/171:54 pm -
1 stop5h 42m
Sat 11/219:10 am -
1 stop7h 12m
Deal found 11/2![American Airlines logo]()
$547
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:05 am -
1 stop5h 57m
Sun 12/69:00 am -
1 stop7h 16m
Deal found 11/2![American Airlines logo]()
$581
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:15 pm -
Nonstop1h 49m
Fri 11/206:49 pm -
1 stop26h 37m
Deal found 11/3![American Airlines logo]()
$890
Last-minute flights from Evansville to ChicagoDiscover last-minute flight deals from Evansville to Chicago. Data last updated November 3, 2026 and is based on user searches.
Discover last-minute flight deals from Evansville to Chicago. Data last updated November 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:15 pm -
Nonstop1h 49m
Tue 11/1010:37 pm -
Nonstop1h 22m
Deal found 11/2![American Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 11/114:15 pm -
Nonstop1h 49m
Wed 11/1810:37 pm -
Nonstop1h 22m
Deal found 11/1![American Airlines logo]()
$361
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:37 am -
Nonstop2h 04m
Sat 11/2811:05 pm -
Nonstop1h 27m
Deal found 11/3![American Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/26:37 am -
Nonstop2h 03m
Tue 12/82:15 pm -
Nonstop1h 23m
Deal found 11/1![American Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:42 pm -
1 stop8h 17m
Tue 12/84:00 pm -
2 stops24h 02m
Deal found 11/1![Multiple Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:08 pm -
Nonstop1h 51m
Sun 12/62:15 pm -
Nonstop1h 23m
Deal found 11/2![American Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 12/54:42 pm -
1 stop8h 26m
Sun 12/610:29 pm -
2 stops21h 07m
Deal found 11/2![Multiple Airlines logo]()
$418
One-way flights from Evansville to ChicagoSearch for one-way flight options from Evansville to Chicago. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
Search for one-way flight options from Evansville to Chicago. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:42 pm -
2 stops28h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/146:37 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![American Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Thu 11/198:08 pm -
3 stops52h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/26:37 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:15 pm -
Nonstop1h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:54 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:40 pm -
2 stops7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$714
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 November 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (American Airlines) |
One-way from | $185 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $569 |
Good round-trip deal | $515 or less |
Good one-way deal | $422 or less |
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 7,457,451 searches. Data last updated November 3, 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
Cheapest round-trip
Quickest round-trip
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Mon 12/14
6:37 am-8:40 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$262
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Tue 3/23
7:05 am-9:00 am
Nonstop1h 55m
Chicago O'Hare Intl
Wed 3/31
10:30 pm-11:59 pm
Nonstop1h 29m
$281
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Thu 11/19
8:08 pm-12:53 am
3 stops52h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$302
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Sat 12/5
4:42 pm-1:08 am
1 stop8h 26m
Chicago O'Hare Intl
Sun 12/6
10:37 pm-7:36 pm
2 stops20h 59m
$411
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Thu 11/19
4:47 pm-10:34 pm
1 stop5h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$475
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Mon 11/16
1:54 pm-7:36 pm
1 stop5h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$475
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Sat 12/5
4:08 pm-5:59 pm
Nonstop1h 51m
Chicago O'Hare Intl
Sun 12/6
6:00 am-11:45 am
1 stop5h 45m
$499
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Tue 11/24
4:47 pm-11:59 pm
1 stop7h 12m
Chicago O'Hare Intl
Sat 11/28
6:41 am-12:14 pm
1 stop5h 33m
$533
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Tue 11/17
1:54 pm-7:36 pm
1 stop5h 42m
Chicago O'Hare Intl
Sat 11/21
9:10 am-4:22 pm
1 stop7h 12m
$547
EvansvilleChicago
EVV Evansville Dress Regional - ORD Chicago O'Hare Intl
EVVORD
Evansville Dress Regional
Fri 12/4
5:05 am-11:02 am
1 stop5h 57m
Chicago O'Hare Intl
Sun 12/6
9:00 am-4:16 pm
1 stop7h 16m
$581
Showing 1-10 of 16 resultsSorted by cheapest first
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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.
EVV-CHI
EVV-ORD
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
EVV-CHI
EVV-ORD
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 November 3, 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 evening could potentially save you up to 56% 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 November 3, 2026.
The most flights from EVV to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 November 3, 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.
Crew
7.9
Boarding
7.4
Overall
7.0
Comfort
7.2
Food
6.4
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Crew
7.9
Boarding
7.4
Overall
7.0
Comfort
7.2
Food
6.4
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Evansville and Chicago flights
Browse other Evansville and Chicago flight options. Last updated on November 3, 2026.
Other flights from Evansville
Browse through other flights departing from Evansville. Flights are based on user searches made on Cheapflights and were last updated on November 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated November 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$331 | Average$464 | FlexibilityNo cancel fee | On-time71% |