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Laredo

$271+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LRD
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Cheap 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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$271
(American Airlines)

One-way from

$271
(American Airlines)

Popular in

January

Cheapest in

April

Average price

$665
Provider with most accurate pricing for Chicago (CHI)-Laredo flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Laredo flights.
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From Chicago (CHI) to Laredo
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One-way flight from Chicago (CHI) to Laredo
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Highest demand for flights based on searches. 18% potential increase in price ($123 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 22, 2025.

This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 11/810:25 amORD - LRD
1 stop7h 47mAmerican Airlines
Mon 11/106:42 pmLRD - ORD
1 stop4h 55mAmerican Airlines
Deal found 10/20$271
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 11/110:35 amORD - LRD
1 stop5h 33mUnited Airlines
Sat 11/89:25 amLRD - ORD
1 stop5h 28mUnited Airlines
Deal found 10/20$283
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/510:25 amORD - LRD
1 stop7h 47mAmerican Airlines
Sun 11/96:20 pmLRD - ORD
1 stop6h 08mAmerican Airlines
Deal found 10/21$289
This United Airlines deal was found by Cheapflights users on 10/21. 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 10/286:00 amORD - LRD
1 stop5h 18mUnited Airlines
Tue 11/412:05 pmLRD - ORD
1 stop5h 03mUnited Airlines
Deal found 10/21$291
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 12/135:18 pmORD - LRD
1 stop5h 20mAmerican Airlines
Tue 12/166:42 pmLRD - ORD
1 stop4h 53mAmerican Airlines
Deal found 10/19$324
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Fri 11/78:50 amORD - LRD
1 stop7h 18mUnited Airlines
Mon 11/105:22 pmLRD - ORD
1 stop6h 53mUnited Airlines
Deal found 10/20$354
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 11/215:10 pmORD - LRD
1 stop6h 28mUnited Airlines
Fri 11/285:22 pmLRD - ORD
1 stop6h 53mUnited Airlines
Deal found 10/21$372
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 12/126:13 pmORD - LRD
1 stop5h 26mUnited Airlines
Sat 1/35:30 pmLRD - ORD
1 stop6h 44mUnited Airlines
Deal found 10/21$373

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 October 22, 2025.
Use the filters below to find and compare flights from Chicago to Laredo that are best for you.

Fly from

Chicago

Fly to

Laredo

Route

Depart

Return

Price

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 11/8

10:25 am-6:12 pm

1 stop7h 47m

Laredo

Mon 11/10

6:42 pm-11:37 pm

1 stop4h 55m

$271

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 11/1

10:35 am-4:08 pm

1 stop5h 33m

Laredo

Sat 11/8

9:25 am-2:53 pm

1 stop5h 28m

$283

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 12/13

5:18 pm-10:38 pm

1 stop5h 20m

Laredo

Tue 12/16

6:42 pm-11:35 pm

1 stop4h 53m

$324

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 11/7

8:50 am-4:08 pm

1 stop7h 18m

Laredo

Mon 11/10

5:22 pm-12:15 am

1 stop6h 53m

$354

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 11/21

5:10 pm-11:38 pm

1 stop6h 28m

Laredo

Fri 11/28

5:22 pm-12:15 am

1 stop6h 53m

$372

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Fri 12/12

6:13 pm-11:39 pm

1 stop5h 26m

Laredo

Sat 1/3

5:30 pm-12:14 am

1 stop6h 44m

$373

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 11/22

6:51 pm-11:54 pm

1 stop5h 03m

Laredo

Sat 11/29

6:26 pm-11:54 pm

1 stop5h 28m

$442

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 11/22

5:10 pm-11:38 pm

1 stop6h 28m

Laredo

Sun 11/30

7:10 am-7:41 am

1 stop24h 31m

$450

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 11/15

10:25 am-6:12 pm

1 stop7h 47m

$271

ChicagoLaredo

ORD - LRD

ORDLRD

Chicago O'Hare Intl

Sat 12/6

2:21 pm-11:19 am

1 stop20h 58m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 12 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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
No data available for this route at this time. Please check back soon.

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 October 22, 2025.
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
8,988 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
8,988 reviews
United Airlines
7.4
Good
8,988 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.2
Good
11,029 reviews
United Airlines
7.4
Good
8,988 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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 33m. Fly via American Airlines or United Airlines to get the fastest option. The distance between Chicago and Laredo, Texas is about 1190 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Currently priced at $204, American Airlines will fly you from Chicago to Laredo, Texas and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $231. You may be able to fly from Chicago to Laredo, Texas for 62% 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.

See more FAQs

Traveling to a place near Laredo?

Book flights to Laredo if you plan to visit one of these locations
Carrizo Springs

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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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$204Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$231Average$552FlexibilityNo cancel feeOn-time69%

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