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Laredo

$245+ Cheap flights from Chicago (CHI) to Laredo, TX (LRD)

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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LRD
Aug 16 — Aug 231
Sun 8/16
Sun 8/23
1 adult, Economy
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Find cheap flights from Chicago to Laredo with Cheapflights

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Cheap flight deals from Chicago to Laredo

Cheapest flights from Chicago to Laredo
Explore the most affordable flight options available from Chicago to Laredo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 17, 2026.

This American Airlines deal was found by Cheapflights users on 7/16. 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 8/152:57 pm
ORD
-
LRD
1 stop5h 00m
American Airlines
Sat 8/224:04 pm
LRD
-
ORD
1 stop8h 14m
American Airlines
Deal found 7/16$245
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/2910:45 am
ORD
-
LRD
1 stop4h 49m
American Airlines
Sat 9/54:04 pm
LRD
-
ORD
1 stop7h 26m
American Airlines
Deal found 7/15$246
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/2712:11 pm
ORD
-
LRD
1 stop7h 25m
American Airlines
Sat 9/56:18 pm
LRD
-
ORD
1 stop6h 00m
American Airlines
Deal found 7/13$282
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Fri 9/48:20 am
ORD
-
LRD
1 stop7h 14m
American Airlines
Mon 9/143:53 pm
LRD
-
ORD
1 stop5h 16m
American Airlines
Deal found 7/13$319
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.
Fri 7/3111:59 am
ORD
-
LRD
1 stop7h 46m
American Airlines
Fri 8/74:04 pm
LRD
-
ORD
1 stop8h 14m
American Airlines
Deal found 7/14$344
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:30 am
ORD
-
LRD
1 stop7h 42m
United Airlines
Mon 1/45:44 pm
LRD
-
ORD
1 stop6h 53m
United Airlines
Deal found 7/17$361
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.
Tue 12/2211:00 am
ORD
-
LRD
1 stop6h 37m
American Airlines
Wed 12/306:07 pm
LRD
-
ORD
1 stop5h 52m
American Airlines
Deal found 7/17$363
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/19:40 am
ORD
-
LRD
1 stop5h 23m
American Airlines
Sun 8/26:53 pm
LRD
-
ORD
1 stop5h 57m
American Airlines
Deal found 7/13$366
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Fri 11/612:11 pm
ORD
-
LRD
1 stop5h 39m
American Airlines
Sun 11/86:20 pm
LRD
-
ORD
1 stop5h 39m
American Airlines
Deal found 7/13$369
This American Airlines deal was found by Cheapflights users on 7/12. 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 7/284:51 pm
ORD
-
LRD
1 stop7h 08m
American Airlines
Sat 8/16:52 pm
LRD
-
ORD
1 stop5h 58m
American Airlines
Deal found 7/12$409
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.
Sat 7/184:51 pm
ORD
-
LRD
1 stop7h 08m
American Airlines
Fri 7/246:53 pm
LRD
-
ORD
1 stop5h 57m
American Airlines
Deal found 7/17$411

Find flight deals from Chicago to Laredo

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Laredo (LRD). 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 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$245
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$680
Provider with most accurate pricing for Chicago (CHI)-Laredo flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Laredo flights.
Search Deals
From Chicago (CHI) to Laredo
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Laredo 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 17, 2026.
Use the filters below to find and compare flights from Chicago to Laredo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 7/31

11:59 am-7:45 pm

1 stop7h 46m

Laredo

Fri 8/7

4:04 pm-12:18 am

1 stop8h 14m

$344
Quickest round-trip

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 7/31

1:25 pm-6:21 pm

1 stop4h 56m

Laredo

Sun 8/2

6:53 pm-12:50 am

1 stop5h 57m

$369

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Tue 7/28

4:51 pm-11:59 pm

1 stop7h 08m

Laredo

Sat 8/1

6:52 pm-12:50 am

1 stop5h 58m

$409

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Thu 8/27

8:29 pm-1:26 pm

2 stops16h 57m

Laredo

Sat 9/5

2:13 pm-9:32 pm

1 stop7h 19m

$450

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 11/6

6:55 am-1:31 pm

1 stop6h 36m

Laredo

Sun 11/8

5:42 pm-2:35 pm

2 stops20h 53m

$487

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Thu 8/6

6:29 am-1:31 pm

1 stop7h 02m

Laredo

Mon 8/10

7:15 am-6:39 pm

2 stops11h 24m

$579

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 7/31

5:45 pm-10:59 pm

1 stop5h 14m

Laredo

Mon 8/3

2:06 pm-6:28 am

2 stops16h 22m

$593

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 7/31

6:29 am-1:31 pm

1 stop7h 02m

Laredo

Sun 8/2

2:06 pm-6:28 am

2 stops16h 22m

$593

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Tue 12/22

6:00 pm-1:12 pm

2 stops19h 12m

Laredo

Wed 12/30

5:44 pm-11:10 pm

1 stop5h 26m

$619

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 9/4

8:40 am-8:16 pm

2 stops11h 36m

Laredo

Mon 9/14

2:13 pm-9:32 pm

1 stop7h 19m

$622

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Compare providers for flights from Chicago to Laredo

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 Chicago to Laredo in July.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 Chicago-Laredo, Texas flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Laredo, Texas flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Laredo, Texas flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Laredo, Texas 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 Chicago-Laredo, Texas 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 Chicago to Laredo

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

What is the cheapest month to book a flight from Chicago to Laredo, Texas?

Currently, October is the cheapest month in which you can book a flight from Chicago to Laredo, Texas (average of $258). Flying from Chicago to Laredo, Texas in March is currently the most expensive (average of $716). 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.

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

Reviews of airlines servicing Laredo

Get insights into the airlines that provide service to Laredo. 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 Laredo. Reviews last updated July 17, 2026.
Read through reviews of airlines operating flights from Chicago to Laredo, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,997 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
United Airlines
7.4
Good
9,997 reviews
United Airlines
7.4
Good
9,997 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
American Airlines
7.1
Good
11,819 reviews
United Airlines
7.4
Good
9,997 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Laredo. 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 into for flights to Laredo from Chicago?

    Most people fly into Laredo (LRD) if they book a flight to Laredo from Chicago. On average, Laredo has 0 inbound flights from Chicago per day from 2 airlines. Laredo is conveniently located just 3.9 mi from Laredo’s city center.

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

    There are many flights that can get you from Chicago to Laredo, Texas in 5h. Fly via American Airlines to get the fastest option. The distance between Chicago and Laredo, Texas is about 1190 mi.

  • What are the cheapest airlines flying from Chicago to Laredo, Texas round-trip?

    Currently priced at $231, United Airlines will fly you from Chicago to Laredo, Texas and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $243. You may be able to fly from Chicago to Laredo, Texas for 42% less than the average price by searching for these airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Laredo 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 Chicago to Laredo, Texas?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Laredo, Texas (average of $258). Flying from Chicago to Laredo, Texas in March is currently the most expensive (average of $716). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Laredo

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Laredo

Discover the top 2 airlines that operate flights from Chicago to Laredo. 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 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$231Average$336FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$243Average$291FlexibilityNo cancel feeOn-time71%

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