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$260+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
LSE — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$329
(American Airlines)

One-way from

$260
(American Airlines)

Good round-trip deal

$476 or less

Good one-way deal

$330 or less
From La Crosse to Chicago (CHI)
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One-way flight from La Crosse to Chicago (CHI)
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Price to beat on a round-trip flight from La Crosse to Chicago (CHI).
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Price to beat on a one-way flight from La Crosse to Chicago (CHI).
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Find 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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 8/3010:48 amLSE - ORD
Nonstop1h 16mAmerican Airlines
Sun 8/318:59 amORD - LSE
Nonstop1h 24mAmerican Airlines
Deal found 8/13$329
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/166:00 amLSE - ORD
Nonstop1h 20mAmerican Airlines
Mon 9/228:20 amORD - LSE
Nonstop1h 19mAmerican Airlines
Deal found 8/13$347
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Fri 8/296:32 pmLSE - ORD
Nonstop1h 18mAmerican Airlines
Tue 9/28:59 amORD - LSE
Nonstop1h 24mAmerican Airlines
Deal found 8/14$435
This American Airlines deal was found by Cheapflights users on 8/13. 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 8/2810:53 amLSE - ORD
Nonstop1h 16mAmerican Airlines
Mon 9/18:59 amORD - LSE
Nonstop1h 24mAmerican Airlines
Deal found 8/13$445
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Tue 11/44:00 pmLSE - ORD
Nonstop1h 24mAmerican Airlines
Thu 11/64:15 pmORD - LSE
Nonstop1h 17mAmerican Airlines
Deal found 8/14$468
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 9/86:39 pmLSE - ORD
Nonstop1h 20mAmerican Airlines
Wed 9/108:43 pmORD - LSE
Nonstop1h 21mAmerican Airlines
Deal found 8/14$733
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sun 8/176:32 pmLSE - ORD
Nonstop1h 18mAmerican Airlines
Thu 8/218:59 amORD - LSE
Nonstop1h 24mAmerican Airlines
Deal found 8/13$777

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 August 14, 2025.
Use the filters below to find and compare flights from La Crosse to Chicago that are best for you.

Fly from

La Crosse

Fly to

Chicago

Route

Depart

Return

Price

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Sat 8/30

10:48 am-12:04 pm

Nonstop1h 16m

Chicago O'Hare Intl

Sun 8/31

8:59 am-10:23 am

Nonstop1h 24m

$329

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Tue 9/16

6:00 am-7:20 am

Nonstop1h 20m

Chicago O'Hare Intl

Mon 9/22

8:20 am-9:39 am

Nonstop1h 19m

$347

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Fri 8/29

6:32 pm-7:50 pm

Nonstop1h 18m

Chicago O'Hare Intl

Tue 9/2

8:59 am-10:23 am

Nonstop1h 24m

$435

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Sat 8/30

10:48 am-12:04 pm

Nonstop1h 16m

Chicago O'Hare Intl

Mon 9/1

4:45 pm-6:02 pm

Nonstop1h 17m

$435

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Thu 8/28

10:53 am-12:09 pm

Nonstop1h 16m

Chicago O'Hare Intl

Mon 9/1

8:59 am-10:23 am

Nonstop1h 24m

$445

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Tue 11/4

4:00 pm-5:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Thu 11/6

4:15 pm-5:32 pm

Nonstop1h 17m

$468

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Tue 11/4

4:00 pm-5:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Fri 11/7

4:15 pm-5:32 pm

Nonstop1h 17m

$468

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Mon 9/8

6:39 pm-7:59 pm

Nonstop1h 20m

Chicago O'Hare Intl

Wed 9/10

8:43 pm-10:04 pm

Nonstop1h 21m

$733

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Tue 9/9

6:00 am-7:20 am

Nonstop1h 20m

Chicago O'Hare Intl

Thu 9/11

10:00 pm-11:17 pm

Nonstop1h 17m

$733

La CrosseChicago

LSE - ORD

LSEORD

La Crosse

Sun 8/17

6:32 pm-7:50 pm

Nonstop1h 18m

Chicago O'Hare Intl

Thu 8/21

8:59 am-10:23 am

Nonstop1h 24m

$777

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 17 results
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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 month to book a flight from La Crosse to Chicago?

Currently, August is the cheapest month in which you can book a flight from La Crosse to Chicago (average of $245). Flying from La Crosse 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 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 August 14, 2025.

It’s typically best to fly out from La Crosse to Chicago in the morning. Doing so could potentially save you 13% on the flight price compared to flying in the afternoon, 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 August 14, 2025.

The most flights from LSE to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 5 outbound flights to Chicago per day.

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

    Currently priced at $317, 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: American Airlines (79%), Envoy Air (79%), Qatar Airways (72%).

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

    Looking at all options, your cheapest flight can be booked for $230. While the most popular route (La Crosse - Chicago O'Hare Intl) can be booked for $327 on average our data indicates $522 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.

  • What is the cheapest month to book a flight from La Crosse to Chicago?

    Currently, August is the cheapest month in which you can book a flight from La Crosse to Chicago (average of $245). Flying from La Crosse 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for La Crosse to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$317Average$435FlexibilityNo cancel feeOn-time71%

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