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$205+ Cheap flights from Laredo, TX (LRD) 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
LRD — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$205
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$366
From Laredo to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($171 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
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Find 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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 11/110:00 amLRD - ORD
1 stop7h 10mAmerican Airlines
Wed 11/510:25 amORD - LRD
1 stop7h 47mAmerican Airlines
Deal found 8/14$205
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/272:18 pmLRD - ORD
1 stop7h 27mAmerican Airlines
Sat 10/44:18 pmORD - LRD
1 stop6h 33mAmerican Airlines
Deal found 8/13$245
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Tue 12/95:58 amLRD - ORD
1 stop6h 07mAmerican Airlines
Mon 12/158:05 amORD - LRD
1 stop8h 03mAmerican Airlines
Deal found 8/14$336
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/267:15 amLRD - ORD
1 stop5h 08mUnited Airlines
Sat 8/309:00 amORD - LRD
1 stop7h 09mUnited Airlines
Deal found 8/14$363
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/17:10 amLRD - ORD
1 stop5h 07mUnited Airlines
Wed 11/52:23 pmORD - LRD
2 stops25h 45mUnited Airlines
Deal found 8/13$364
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:00 amLRD - ORD
2 stops11h 50mUnited Airlines
Sat 10/412:45 pmORD - LRD
1 stop7h 11mUnited Airlines
Deal found 8/13$365
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1710:50 pmLRD - ORD
2 stops21h 37mMultiple Airlines
Mon 11/36:35 amORD - LRD
1 stop14h 17mMultiple Airlines
Deal found 8/13$366
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:25 pmLRD - ORD
1 stop6h 49mUnited Airlines
Mon 9/295:50 pmORD - LRD
1 stop5h 43mUnited Airlines
Deal found 8/14$373
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2610:41 pmLRD - ORD
1 stop13h 10mMultiple Airlines
Mon 9/296:00 amORD - LRD
2 stops15h 20mMultiple Airlines
Deal found 8/14$393
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 8/216:25 pmLRD - ORD
1 stop5h 34mAmerican Airlines
Mon 8/254:21 pmORD - LRD
1 stop6h 29mAmerican Airlines
Deal found 8/14$418
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/295:15 pmLRD - ORD
1 stop7h 00mUnited Airlines
Tue 9/25:50 pmORD - LRD
1 stop5h 44mUnited Airlines
Deal found 8/14$419

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 August 14, 2025.
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

Sat 11/1

6:39 pm-11:42 pm

1 stop5h 03m

Chicago O'Hare Intl

Wed 11/5

11:46 am-6:12 pm

1 stop6h 26m

$205

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 9/27

6:44 pm-11:59 pm

1 stop5h 15m

Chicago O'Hare Intl

Sat 10/4

5:16 pm-10:51 pm

1 stop5h 35m

$205

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 12/9

5:58 am-12:05 pm

1 stop6h 07m

Chicago O'Hare Intl

Mon 12/15

8:05 am-4:08 pm

1 stop8h 03m

$336

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 8/27

5:15 pm-12:15 am

1 stop7h 00m

Chicago O'Hare Intl

Sat 8/30

9:00 am-4:09 pm

1 stop7h 09m

$363

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 8/26

7:15 am-12:23 pm

1 stop5h 08m

Chicago O'Hare Intl

Sat 8/30

9:00 am-4:09 pm

1 stop7h 09m

$363

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 11/1

7:10 am-12:17 pm

1 stop5h 07m

Chicago O'Hare Intl

Wed 11/5

2:23 pm-4:08 pm

2 stops25h 45m

$364

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 12/9

12:05 pm-7:46 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 12/15

5:50 pm-11:19 am

2 stops17h 29m

$365

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 9/27

7:00 am-6:50 pm

2 stops11h 50m

Chicago O'Hare Intl

Sat 10/4

12:45 pm-7:56 pm

1 stop7h 11m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 August 14, 2025.
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
10,000 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.5

Overall

7.2

Crew

8.0

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.5

Overall

7.2

Crew

8.0

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation

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.

  • 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 $243 on this airline. American Airlines is currently priced 43% 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.

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

    Currently, August is the cheapest month in which you can book a flight from Laredo, Texas to Chicago (average of $245). Flying from Laredo, Texas to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Laredo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$243Average$323FlexibilityNo cancel feeOn-time71%

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