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$354+ Cheap flights from Laramie (LAR) 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
LAR — CHI
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from Laramie to Chicago

Cheapest flights from Laramie to Chicago
Explore the most affordable flight options available from Laramie to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This United Airlines deal was found by Cheapflights users on 5/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:20 pm
LAR
-
ORD
1 stop4h 36m
United Airlines
Sun 5/2412:40 pm
ORD
-
LAR
1 stop5h 51m
United Airlines
Deal found 5/5$354
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:30 am
LAR
-
ORD
1 stop16h 19m
United Airlines
Wed 5/2710:54 am
ORD
-
LAR
1 stop7h 37m
United Airlines
Deal found 5/1$397
This United Airlines deal was found by Cheapflights users on 5/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:30 pm
LAR
-
ORD
1 stop4h 29m
United Airlines
Sat 9/55:45 pm
ORD
-
LAR
1 stop5h 11m
United Airlines
Deal found 5/5$404
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:15 pm
LAR
-
ORD
1 stop5h 29m
United Airlines
Mon 5/2512:40 pm
ORD
-
LAR
1 stop5h 51m
United Airlines
Deal found 5/6$425
This United Airlines deal was found by Cheapflights users on 5/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:15 pm
LAR
-
ORD
1 stop5h 29m
United Airlines
Wed 6/101:30 pm
ORD
-
LAR
1 stop5h 01m
United Airlines
Deal found 5/5$507

Find flight deals from Laramie to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Laramie (LAR) 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 May 6, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$354
(United Airlines)
Provider with most accurate pricing for Laramie Gen. Brees Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Laramie Gen. Brees Field-Chicago (CHI) flights.
Search Deals
From Laramie Gen. Brees Field to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Laramie 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 May 6, 2026.
Use the filters below to find and compare flights from Laramie to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Wed 5/20

6:20 pm-11:56 pm

1 stop4h 36m

Chicago O'Hare Intl

Sun 5/24

12:40 pm-5:31 pm

1 stop5h 51m

$354

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Sat 5/23

5:30 am-10:49 pm

1 stop16h 19m

Chicago O'Hare Intl

Wed 5/27

10:54 am-5:31 pm

1 stop7h 37m

$397
Quickest round-trip

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Wed 9/2

6:30 pm-11:59 pm

1 stop4h 29m

Chicago O'Hare Intl

Sat 9/5

5:45 pm-9:56 pm

1 stop5h 11m

$404

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Thu 5/21

5:30 am-11:23 am

1 stop4h 53m

Chicago O'Hare Intl

Mon 5/25

7:45 pm-5:31 pm

2 stops22h 46m

$603

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Mon 5/18

6:20 pm-8:24 pm

1 stop25h 04m

Chicago O'Hare Intl

Fri 5/22

5:00 am-9:59 pm

1 stop17h 59m

$612

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Sun 5/17

6:20 pm-11:57 pm

1 stop4h 37m

Chicago O'Hare Intl

Thu 5/21

1:05 pm-5:31 pm

1 stop5h 26m

$736
Cheapest one-way
Quickest one-way

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Fri 5/15

5:30 am-11:10 am

1 stop4h 40m

$360

LaramieChicago

LAR - ORD

LARORD

Laramie Gen. Brees Field

Sat 8/8

5:30 am-12:29 pm

2 stops5h 59m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Laramie-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Laramie-Chicago flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Laramie-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Laramie-Chicago flights, Cheapflights users trust Expedia the most. Expedia 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 Laramie-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 Laramie to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Laramie 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 Laramie to Chicago
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Laramie 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 Laramie to Chicago?

    Located just 4.3 mi from the city center, Laramie Gen. Brees Field is the airport most travelers will use when flying to Chicago from Laramie. Booking flights from Gen. Brees Field (LAR) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

  • How long is the flight from Laramie to Chicago?

    For as low as $354, United Airlines can have you in Chicago from Laramie in 4h 36m. The distance from Laramie to Chicago is about 916 mi.

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

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

  • How can I find direct flights from Laramie to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Laramie 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
Hammond
Porter

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