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$216+ Cheap flights from Laredo, TX (LRD) 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
LRD — CHI
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Laredo to Chicago

Cheapest flights from Laredo to Chicago
Explore the most affordable flight options available from Laredo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.

This American Airlines deal was found by Cheapflights users on 1/18. 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.
Sun 2/86:03 am
LRD
-
ORD
1 stop4h 51m
American Airlines
Sun 2/155:00 am
ORD
-
LRD
1 stop5h 13m
American Airlines
Deal found 1/18$279
This American Airlines deal was found by Cheapflights users on 1/19. 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 2/56:03 am
LRD
-
ORD
1 stop5h 52m
American Airlines
Wed 2/1110:19 am
ORD
-
LRD
1 stop7h 19m
American Airlines
Deal found 1/19$296
This United Airlines deal was found by Cheapflights users on 1/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/213:25 pm
LRD
-
ORD
1 stop6h 01m
United Airlines
Wed 2/115:40 am
ORD
-
LRD
1 stop5h 48m
United Airlines
Deal found 1/18$301
This United Airlines deal was found by Cheapflights users on 1/20. 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 2/43:25 pm
LRD
-
ORD
1 stop6h 01m
United Airlines
Sun 2/85:40 am
ORD
-
LRD
1 stop5h 48m
United Airlines
Deal found 1/20$309
This United Airlines deal was found by Cheapflights users on 1/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:23 pm
LRD
-
ORD
1 stop7h 22m
United Airlines
Sun 5/105:30 am
ORD
-
LRD
1 stop5h 59m
United Airlines
Deal found 1/19$324
This American Airlines deal was found by Cheapflights users on 1/20. 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 3/66:28 pm
LRD
-
ORD
1 stop5h 08m
American Airlines
Tue 3/106:10 am
ORD
-
LRD
1 stop7h 45m
American Airlines
Deal found 1/20$355
This United Airlines deal was found by Cheapflights users on 1/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:12 pm
LRD
-
ORD
1 stop7h 41m
United Airlines
Sat 2/282:00 pm
ORD
-
LRD
1 stop6h 02m
United Airlines
Deal found 1/19$372
This United Airlines deal was found by Cheapflights users on 1/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/163:17 pm
LRD
-
ORD
1 stop6h 21m
United Airlines
Mon 3/237:35 am
ORD
-
LRD
1 stop7h 07m
United Airlines
Deal found 1/18$392
This United Airlines deal was found by Cheapflights users on 1/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/227:15 am
LRD
-
ORD
1 stop5h 45m
United Airlines
Thu 1/295:40 am
ORD
-
LRD
1 stop5h 48m
United Airlines
Deal found 1/19$409
This American Airlines deal was found by Cheapflights users on 1/17. 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 7/13:47 pm
LRD
-
ORD
1 stop7h 34m
American Airlines
Sat 8/15:00 am
ORD
-
LRD
1 stop5h 00m
American Airlines
Deal found 1/17$433
This United Airlines deal was found by Cheapflights users on 1/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/297:15 am
LRD
-
ORD
1 stop5h 45m
United Airlines
Sat 1/315:37 am
ORD
-
LRD
1 stop5h 51m
United Airlines
Deal found 1/17$434

Find flight deals from Laredo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Laredo (LRD) 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 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$279
(American Airlines)

One-way from

$216
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$454
Provider with most accurate pricing for Laredo-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Laredo-Chicago (CHI) flights.
Search Deals
From Laredo to Chicago (CHI)
Search Deals
One-way flight from Laredo to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Laredo 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 20, 2026.
Use the filters below to find and compare flights from Laredo to Chicago that are best for you.

Fly from

Laredo

Fly to

Chicago

Route

Depart

Return

Price

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 2/5

6:03 am-11:55 am

1 stop5h 52m

Chicago O'Hare Intl

Wed 2/11

10:19 am-5:38 pm

1 stop7h 19m

$296

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 2/4

3:25 pm-9:26 pm

1 stop6h 01m

Chicago O'Hare Intl

Sun 2/8

5:40 am-11:28 am

1 stop5h 48m

$309

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 5/7

5:23 pm-12:45 am

1 stop7h 22m

Chicago O'Hare Intl

Sun 5/10

5:30 am-11:29 am

1 stop5h 59m

$324

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 3/6

6:28 pm-11:36 pm

1 stop5h 08m

Chicago O'Hare Intl

Tue 3/10

6:10 am-1:55 pm

1 stop7h 45m

$355

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 2/24

12:12 pm-7:53 pm

1 stop7h 41m

Chicago O'Hare Intl

Sat 2/28

2:00 pm-8:02 pm

1 stop6h 02m

$372

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 3/16

3:17 pm-9:38 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 3/23

7:35 am-2:42 pm

1 stop7h 07m

$392

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 7/1

3:47 pm-11:21 pm

1 stop7h 34m

Chicago O'Hare Intl

Sat 8/1

5:00 am-10:00 am

1 stop5h 00m

$433

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 3/16

10:25 pm-6:08 am

1 stop31h 43m

Chicago O'Hare Intl

Mon 3/23

5:01 am-9:35 pm

2 stops16h 34m

$434

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 4/2

12:13 pm-7:44 am

1 stop19h 31m

Chicago O'Hare Intl

Sun 4/12

5:49 am-11:28 am

1 stop5h 39m

$447

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 3/6

9:20 pm-6:08 am

1 stop8h 48m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 16 results
1
2

Compare providers for flights from Laredo 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 Laredo to Chicago in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

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

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

How much does it cost to fly round-trip from Laredo, Texas to Chicago?

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 January 20, 2026.
Get a feel of what it's like to fly with American Airlines from Laredo to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,164 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

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
7.2
Good
11,164 reviews
American Airlines
7.2
Good
11,164 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

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 Laredo 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 Laredo to Chicago?

    Laredo (LRD) is the airport you will fly out of if you book a flight from Laredo to Chicago. You should not have trouble finding flights to Chicago from Laredo; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Laredo airport to Chicago. It is only a 3.9 mi journey to Laredo (LRD) from Laredo’s city center.

  • How long is the flight from Laredo, Texas to Chicago?

    A quick flight from Laredo, Texas to Chicago can take about 5h 52m. American Airlines provides one of the quickest options available for as low as $296. The distance between Laredo, Texas and Chicago is about 1190 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Laredo, Texas to Chicago round-trip?

    Our cheapest airline available from Laredo, Texas to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $204 on this airline. American Airlines is currently priced 49% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Laredo 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
Lansing
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Hammond
Porter
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Top airline flying from Laredo to Chicago

Discover the top airline that operate flights from Laredo 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 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$204Average$323FlexibilityNo cancel feeOn-time71%

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