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$225+ Cheap flights from Laredo (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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
LRD — CHI
Apr 8 — Apr 151
Wed 4/8
Wed 4/15
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 March 9, 2026.

This American Airlines deal was found by Cheapflights users on 3/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:48 pm
LRD
-
ORD
1 stop5h 00m
American Airlines
Tue 4/145:00 am
ORD
-
LRD
1 stop4h 54m
American Airlines
Deal found 3/5$225
This American Airlines deal was found by Cheapflights users on 3/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:48 pm
LRD
-
ORD
1 stop5h 00m
American Airlines
Sat 4/256:56 pm
ORD
-
LRD
1 stop5h 02m
American Airlines
Deal found 3/5$226
This American Airlines deal was found by Cheapflights users on 3/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:48 pm
LRD
-
ORD
1 stop5h 00m
American Airlines
Sun 4/265:00 am
ORD
-
LRD
1 stop4h 54m
American Airlines
Deal found 3/5$262
This American Airlines deal was found by Cheapflights users on 3/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:48 pm
LRD
-
ORD
1 stop5h 00m
American Airlines
Mon 4/275:00 am
ORD
-
LRD
1 stop4h 54m
American Airlines
Deal found 3/6$297
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Fri 4/173:15 pm
LRD
-
ORD
1 stop5h 00m
United Airlines
Sun 4/197:30 am
ORD
-
LRD
1 stop7h 00m
United Airlines
Deal found 3/5$299
This American Airlines deal was found by Cheapflights users on 3/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:48 pm
LRD
-
ORD
1 stop5h 00m
American Airlines
Mon 4/206:56 pm
ORD
-
LRD
1 stop5h 02m
American Airlines
Deal found 3/5$301
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Sat 10/245:20 pm
LRD
-
ORD
1 stop6h 50m
United Airlines
Wed 10/286:25 pm
ORD
-
LRD
1 stop4h 52m
United Airlines
Deal found 3/5$305
This United Airlines deal was found by Cheapflights users on 3/8. 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 3/203:17 pm
LRD
-
ORD
1 stop6h 21m
United Airlines
Tue 3/318:51 am
ORD
-
LRD
1 stop5h 39m
United Airlines
Deal found 3/8$359
This American Airlines deal was found by Cheapflights users on 3/8. 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 3/242:25 pm
LRD
-
ORD
1 stop7h 00m
American Airlines
Sat 3/286:51 pm
ORD
-
LRD
1 stop5h 08m
American Airlines
Deal found 3/8$382
This United Airlines deal was found by Cheapflights users on 3/6. 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 5/145:23 pm
LRD
-
ORD
1 stop8h 04m
United Airlines
Mon 5/185:30 am
ORD
-
LRD
1 stop5h 59m
United Airlines
Deal found 3/6$397
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:37 pm
LRD
-
ORD
1 stop8h 31m
Multiple Airlines
Sun 4/262:00 pm
ORD
-
LRD
2 stops30h 47m
Multiple Airlines
Deal found 3/5$399

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 March 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$225
(American Airlines)

Popular in

July

Cheapest in

August

Average price

$394
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 9, 2026.
Use the filters below to find and compare flights from Laredo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 4/20

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Mon 4/27

5:00 am-9:54 am

1 stop4h 54m

$297

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 4/24

3:15 pm-11:15 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 4/26

7:30 am-2:30 pm

1 stop7h 00m

$299

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 4/23

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Sun 4/26

5:00 am-9:54 am

1 stop4h 54m

$299

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 3/20

3:17 pm-9:38 pm

1 stop6h 21m

Chicago O'Hare Intl

Tue 3/31

8:51 am-2:30 pm

1 stop5h 39m

$359

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 5/14

5:23 pm-1:27 am

1 stop8h 04m

Chicago O'Hare Intl

Mon 5/18

5:30 am-11:29 am

1 stop5h 59m

$397

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 3/20

3:17 pm-11:08 pm

1 stop7h 51m

Chicago O'Hare Intl

Tue 3/24

8:53 am-2:42 pm

1 stop5h 49m

$413

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 4/11

7:15 am-8:50 pm

2 stops13h 35m

Chicago O'Hare Intl

Tue 4/14

5:48 am-11:28 am

1 stop5h 40m

$462

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 4/20

3:15 pm-9:34 am

2 stops18h 19m

Chicago O'Hare Intl

Mon 4/27

5:48 am-11:28 am

1 stop5h 40m

$477

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 4/23

3:15 pm-9:34 am

2 stops18h 19m

Chicago O'Hare Intl

Sun 4/26

7:30 am-2:30 pm

1 stop7h 00m

$497

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 5/22

9:30 am-9:05 am

1 stop23h 35m

Chicago O'Hare Intl

Mon 5/25

5:30 am-10:59 pm

1 stop17h 29m

$521

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 15 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust 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 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 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 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 March 9, 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
7.1
Good
11,403 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Overall

7.1

Entertainment

6.9

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
7.1
Good
11,403 reviews
American Airlines
7.1
Good
11,403 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Overall

7.1

Entertainment

6.9

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. American Airlines provides one of the quickest options available for as low as $297. 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 46% 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
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Laredo to Chicago

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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 March 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$204Average$323FlexibilityNo cancel feeOn-time71%

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