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$197+ Cheap flights from La Crosse (LSE) 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
LSE — CHI
Aug 18 — Aug 251
Tue 8/18
Tue 8/25
1 adult, Economy
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Cheap flight deals from La Crosse to Chicago

Cheapest flights from La Crosse to Chicago
Explore the most affordable flight options available from La Crosse to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 19, 2026.

This American Airlines deal was found by Cheapflights users on 7/18. 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 10/76:50 pm
LSE
-
ORD
Nonstop1h 35m
American Airlines
Tue 10/1310:40 pm
ORD
-
LSE
Nonstop1h 19m
American Airlines
Deal found 7/18$229
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/35:53 pm
LSE
-
ORD
Nonstop1h 36m
American Airlines
Thu 8/1311:00 pm
ORD
-
LSE
Nonstop1h 22m
American Airlines
Deal found 7/18$244
This American Airlines deal was found by Cheapflights users on 7/17. 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 7/2912:01 pm
LSE
-
ORD
Nonstop1h 24m
American Airlines
Fri 8/710:10 am
ORD
-
LSE
Nonstop1h 21m
American Airlines
Deal found 7/17$259
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/145:20 pm
LSE
-
ORD
Nonstop1h 33m
American Airlines
Sun 8/1610:04 am
ORD
-
LSE
Nonstop1h 19m
American Airlines
Deal found 7/18$343
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/75:20 pm
LSE
-
ORD
Nonstop1h 33m
American Airlines
Sun 8/910:04 am
ORD
-
LSE
Nonstop1h 19m
American Airlines
Deal found 7/18$358
This American Airlines deal was found by Cheapflights users on 7/17. 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 7/175:53 pm
LSE
-
ORD
Nonstop1h 36m
American Airlines
Sun 7/1910:37 pm
ORD
-
LSE
Nonstop1h 22m
American Airlines
Deal found 7/17$389
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/276:00 am
LSE
-
ORD
Nonstop1h 26m
American Airlines
Sat 8/2910:35 am
ORD
-
LSE
Nonstop1h 19m
American Airlines
Deal found 7/14$406
This American Airlines deal was found by Cheapflights users on 7/18. 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 7/185:41 pm
LSE
-
ORD
Nonstop1h 41m
American Airlines
Sat 7/2511:00 pm
ORD
-
LSE
Nonstop1h 22m
American Airlines
Deal found 7/18$409
This American Airlines deal was found by Cheapflights users on 7/19. 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 7/236:00 am
LSE
-
ORD
Nonstop1h 30m
American Airlines
Mon 7/2710:37 pm
ORD
-
LSE
Nonstop1h 22m
American Airlines
Deal found 7/19$424
This American Airlines deal was found by Cheapflights users on 7/14. 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 7/155:53 pm
LSE
-
ORD
Nonstop1h 36m
American Airlines
Sat 7/183:48 pm
ORD
-
LSE
Nonstop1h 23m
American Airlines
Deal found 7/14$425

Find flight deals from La Crosse to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from La Crosse (LSE) 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 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(American Airlines)

One-way from

$197
(Kiwi.com)

Good round-trip deal

$420 or less

Good one-way deal

$411 or less
Provider with most accurate pricing for La Crosse-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for La Crosse-Chicago (CHI) flights.
Search Deals
From La Crosse to Chicago (CHI)
Search Deals
One-way flight from La Crosse to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from La Crosse to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from La Crosse to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from La Crosse 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 19, 2026.
Use the filters below to find and compare flights from La Crosse to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Wed 10/7

6:50 pm-8:25 pm

Nonstop1h 35m

Chicago O'Hare Intl

Tue 10/13

10:40 pm-11:59 pm

Nonstop1h 19m

$229

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Thu 11/5

6:45 pm-8:11 pm

Nonstop1h 26m

Chicago O'Hare Intl

Sun 11/8

4:40 pm-6:03 pm

Nonstop1h 23m

$229

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Fri 9/18

5:22 pm-7:02 pm

Nonstop1h 40m

Chicago O'Hare Intl

Sun 9/20

9:56 am-11:22 am

Nonstop1h 26m

$229

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Thu 10/8

6:50 pm-8:25 pm

Nonstop1h 35m

Chicago O'Hare Intl

Sun 10/11

10:40 pm-11:59 pm

Nonstop1h 19m

$244

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Mon 8/3

5:53 pm-7:29 pm

Nonstop1h 36m

Chicago O'Hare Intl

Thu 8/13

11:00 pm-12:22 am

Nonstop1h 22m

$244
Quickest round-trip

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Wed 7/29

12:01 pm-1:25 pm

Nonstop1h 24m

Chicago O'Hare Intl

Fri 8/7

10:10 am-11:31 am

Nonstop1h 21m

$259

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Sat 1/9

6:15 am-7:38 am

Nonstop1h 23m

Chicago O'Hare Intl

Tue 1/12

7:30 am-8:56 am

Nonstop1h 26m

$299
Cheapest one-way

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Sun 8/16

6:30 pm-12:50 pm

3 stops42h 20m

$197

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Sun 10/18

6:00 pm-8:15 am

3 stops38h 15m

$227

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Thu 1/14

9:42 am-11:06 am

Nonstop1h 24m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from La Crosse 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 La Crosse to Chicago in July.
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 La Crosse-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on La Crosse-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from La Crosse-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on La Crosse-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 La Crosse-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 La Crosse to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from La Crosse 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 La Crosse to Chicago

What is the cheapest time of day to fly from LSE to CHI?

Find hourly flight availability from La Crosse 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 19, 2026.

It’s typically best to fly out from La Crosse to Chicago in the afternoon. Doing so could potentially save you 56% on the flight price compared to flying in the evening, which is usually more expensive.

Weekly flight availability from La Crosse to Chicago

Explore weekly flight availability from La Crosse 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 July 19, 2026.

The most flights from LSE to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Thursday, 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 July 19, 2026.
Read through reviews of airlines operating flights from La Crosse 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
11,822 reviews

Food

6.4

Comfort

7.2

Overall

7.1

Boarding

7.5

Crew

7.9

Entertainment

6.8

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
11,822 reviews
American Airlines
7.1
Good
11,822 reviews

Food

6.4

Comfort

7.2

Overall

7.1

Boarding

7.5

Crew

7.9

Entertainment

6.8

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 La Crosse 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 La Crosse to Chicago?

    La Crosse (LSE), located 5.4 mi from the city center, is the airport you fly out of when you book flights from La Crosse to Chicago. 1 airline have flights from La Crosse to Chicago on a regular basis. Booking flights from La Crosse to Chicago should not be difficult; the airport handles an average of 6 outbound flights to Chicago per day.

  • How long is the flight from La Crosse to Chicago?

    Departing from La Crosse to Chicago will take you 1h 26m. The distance from La Crosse to Chicago is about 214 mi. Most flights are nonstop.

  • What is the cheapest airline to fly from La Crosse to Chicago round-trip?

    Currently priced at $168, American Airlines will fly you from La Crosse to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip.

  • What are the most reliable airlines from La Crosse to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from La Crosse to Chicago on time: Qatar Airways (89%), American Airlines (84%), Envoy Air (84%).

  • What are the cheapest flights from La Crosse to Chicago?

    Looking at all options, your cheapest flight can be booked for $185. While the most popular route (La Crosse - Chicago O'Hare Intl) can be booked for $229 on average, our data indicates $757 when flying from La Crosse to Chicago.

  • Can I find deals for flights from La Crosse to Chicago that include hotel bookings?

    Yes. In addition to deals on La Crosse to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from La Crosse to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from La Crosse to Chicago.

  • Can I find deals for business class flights from La Crosse to Chicago?

    Yes. Cheapflights offers flight deals from La Crosse 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
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from La Crosse to Chicago

Discover the top airline that operate flights from La Crosse 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 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$168Average$367FlexibilityNo cancel feeOn-time71%

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