$325+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
LSE — CHI
Feb 5 — Feb 121
1 adult, Economy
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Find cheap flights from La Crosse 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 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 January 6, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $327 (American Airlines) |
One-way from | $325 (Kiwi.com) |
Good round-trip deal | $480 or less |
Good one-way deal | $398 or less |
Find flight deals from La Crosse to Chicago
Cheapest flights from La Crosse to ChicagoExplore 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 January 6, 2026.
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 January 6, 2026.
This American Airlines deal was found by Cheapflights users on 1/4. 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 2/105:08 pmLSE - ORD
Nonstop1h 32mAmerican Airlines
Tue 2/2412:45 pmORD - LSE
Nonstop1h 21mAmerican Airlines
Deal found 1/4![American Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 1/4. 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 8/316:37 pmLSE - ORD
Nonstop1h 17mAmerican Airlines
Wed 9/168:00 amORD - LSE
Nonstop1h 12mAmerican Airlines
Deal found 1/4![American Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/2011:31 amLSE - ORD
Nonstop1h 20mAmerican Airlines
Sun 2/2210:19 pmORD - LSE
Nonstop1h 17mAmerican Airlines
Deal found 1/6![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/711:37 amLSE - ORD
Nonstop1h 26mAmerican Airlines
Wed 1/149:00 pmORD - LSE
Nonstop1h 16mAmerican Airlines
Deal found 1/6![American Airlines logo]()
$365
This American Airlines deal was found by Cheapflights users on 1/5. 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 3/1211:34 amLSE - ORD
Nonstop1h 20mAmerican Airlines
Mon 3/164:40 pmORD - LSE
Nonstop1h 19mAmerican Airlines
Deal found 1/5![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 1/5. 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 1/105:08 pmLSE - ORD
Nonstop1h 32mAmerican Airlines
Sun 1/112:59 pmORD - LSE
Nonstop1h 17mAmerican Airlines
Deal found 1/5![American Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 1/4. 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 5/96:32 pmLSE - ORD
Nonstop1h 29mAmerican Airlines
Mon 5/114:38 pmORD - LSE
Nonstop1h 24mAmerican Airlines
Deal found 1/4![American Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 1/4. 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 5/76:32 pmLSE - ORD
Nonstop1h 29mAmerican Airlines
Mon 5/1110:31 pmORD - LSE
Nonstop1h 23mAmerican Airlines
Deal found 1/4![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 1/5. 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 1/205:08 pmLSE - ORD
Nonstop1h 32mAmerican Airlines
Sat 1/249:00 pmORD - LSE
Nonstop1h 16mAmerican Airlines
Deal found 1/5![American Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 1/5. 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 1/96:00 amLSE - ORD
Nonstop1h 30mAmerican Airlines
Sun 1/119:00 pmORD - LSE
Nonstop1h 16mAmerican Airlines
Deal found 1/5![American Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 1/5. 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 1/135:08 pmLSE - ORD
Nonstop1h 32mAmerican Airlines
Fri 1/169:00 pmORD - LSE
Nonstop1h 16mAmerican Airlines
Deal found 1/5![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 1/4. 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 5/96:32 pmLSE - ORD
Nonstop1h 29mAmerican Airlines
Sat 5/910:31 pmORD - LSE
Nonstop1h 23mAmerican Airlines
Deal found 1/4![American Airlines logo]()
$713
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 January 6, 2026.
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
Tue 2/10
5:08 pm-6:40 pm
Nonstop1h 32m
Chicago O'Hare Intl
Tue 2/24
12:45 pm-2:06 pm
Nonstop1h 21m
$327
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Fri 2/20
11:31 am-12:51 pm
Nonstop1h 20m
Chicago O'Hare Intl
Sun 2/22
10:19 pm-11:36 pm
Nonstop1h 17m
$351
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Thu 3/12
11:34 am-12:54 pm
Nonstop1h 20m
Chicago O'Hare Intl
Mon 3/16
4:40 pm-5:59 pm
Nonstop1h 19m
$367
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Sat 1/10
5:08 pm-6:40 pm
Nonstop1h 32m
Chicago O'Hare Intl
Sun 1/11
2:59 pm-4:16 pm
Nonstop1h 17m
$383
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Tue 1/20
5:08 pm-6:40 pm
Nonstop1h 32m
Chicago O'Hare Intl
Sat 1/24
9:00 pm-10:16 pm
Nonstop1h 16m
$435
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Fri 1/9
6:00 am-7:30 am
Nonstop1h 30m
Chicago O'Hare Intl
Sun 1/11
9:00 pm-10:16 pm
Nonstop1h 16m
$475
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Sun 1/11
11:37 am-1:03 pm
Nonstop1h 26m
Chicago O'Hare Intl
Sun 1/18
9:00 pm-10:16 pm
Nonstop1h 16m
$475
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Tue 1/13
5:08 pm-6:40 pm
Nonstop1h 32m
Chicago O'Hare Intl
Fri 1/16
9:00 pm-10:16 pm
Nonstop1h 16m
$520
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Mon 1/12
6:00 am-7:30 am
Nonstop1h 30m
Chicago O'Hare Intl
Wed 1/14
9:45 am-11:07 am
Nonstop1h 22m
$714
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Sun 1/18
5:08 pm-6:40 pm
Nonstop1h 32m
Chicago O'Hare Intl
Thu 1/22
2:59 pm-4:16 pm
Nonstop1h 17m
$739
Showing 1-10 of 18 results
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 January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star |
- Most accurate provider: When it comes to deals on La Crosse-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on La Crosse-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 month to book a flight from La Crosse to Chicago?
Currently, February is the cheapest month in which you can book a flight from La Crosse to Chicago (average of $180). Flying from La Crosse to Chicago in September is currently the most expensive (average of $364). 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 January 6, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from La Crosse to Chicago as you normally would.
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 January 6, 2026.
The most flights from LSE to CHI are scheduled on a Tuesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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.
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 January 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$347 | Average$435 | FlexibilityNo cancel fee | On-time71% |