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$148+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
LRD — CHI
nov. 5 — nov. 121
mié. 11/5
mié. 11/12
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 octubre 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(American Airlines)

One-way from

$148
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$428
Provider with most accurate pricing for Laredo-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Laredo-Chicago (CHI) flights.
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From Laredo to Chicago (CHI)
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One-way flight from Laredo to Chicago (CHI)
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Highest demand for flights based on searches. 28% potential increase in price ($165 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($35 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 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 octubre 6, 2025.

This American Airlines deal was found by Cheapflights users on 10/6. 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.
sáb. 11/16:39 pmLRD - ORD
1 stop5h 03mAmerican Airlines
mié. 11/57:25 amORD - LRD
1 stop6h 29mAmerican Airlines
Deal found 10/6$273
This American Airlines deal was found by Cheapflights users on 10/6. 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.
mar. 10/2110:00 amLRD - ORD
1 stop5h 06mAmerican Airlines
sáb. 10/254:17 pmORD - LRD
1 stop6h 26mAmerican Airlines
Deal found 10/6$283
This United Airlines deal was found by Cheapflights users on 10/6. 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.
sáb. 11/17:10 amLRD - ORD
1 stop5h 07mUnited Airlines
mié. 11/52:23 pmORD - LRD
2 stops25h 45mUnited Airlines
Deal found 10/6$405
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
lun. 10/209:52 pmLRD - ORD
2 stops41h 16mMultiple Airlines
vie. 10/246:35 amORD - LRD
1 stop15h 25mMultiple Airlines
Deal found 10/5$426
This United Airlines deal was found by Cheapflights users on 10/6. 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.
mar. 10/219:15 amLRD - ORD
2 stops10h 55mUnited Airlines
sáb. 10/256:00 amORD - LRD
1 stop5h 14mUnited Airlines
Deal found 10/6$455
This United Airlines deal was found by Cheapflights users on 10/4. 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.
dom. 12/145:27 pmLRD - ORD
2 stops14h 36mUnited Airlines
mié. 12/178:50 amORD - LRD
2 stops14h 49mUnited Airlines
Deal found 10/4$504

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 octubre 6, 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

sáb. 11/1

6:39 pm-11:42 pm

1 stop5h 03m

Chicago O'Hare Intl

mié. 11/5

7:25 am-1:54 pm

1 stop6h 29m

$273

LaredoChicago

LRD - ORD

LRDORD

Laredo

mar. 10/21

10:00 am-3:06 pm

1 stop5h 06m

Chicago O'Hare Intl

sáb. 10/25

4:17 pm-10:43 pm

1 stop6h 26m

$283

LaredoChicago

LRD - ORD

LRDORD

Laredo

sáb. 11/1

9:25 am-5:08 pm

1 stop7h 43m

Chicago O'Hare Intl

mié. 11/5

8:50 am-11:18 am

2 stops26h 28m

$405

LaredoChicago

LRD - ORD

LRDORD

Laredo

mar. 10/21

9:15 am-8:10 pm

2 stops10h 55m

Chicago O'Hare Intl

sáb. 10/25

6:00 am-11:14 am

1 stop5h 14m

$455

LaredoChicago

LRD - ORD

LRDORD

Laredo

lun. 10/20

9:52 pm-8:48 pm

1 stop22h 56m

Chicago O'Hare Intl

vie. 10/24

6:35 am-10:00 pm

1 stop15h 25m

$458

LaredoChicago

LRD - ORD

LRDORD

Laredo

dom. 12/14

5:27 pm-8:03 am

2 stops14h 36m

Chicago O'Hare Intl

mié. 12/17

8:50 am-11:39 pm

2 stops14h 49m

$504

LaredoChicago

LRD - ORD

LRDORD

Laredo

lun. 11/3

9:42 pm-7:28 am

2 stops33h 46m

$148

LaredoChicago

LRD - ORD

LRDORD

Laredo

mar. 11/4

5:22 pm-8:05 am

2 stops14h 43m

$248

LaredoChicago

LRD - ORD

LRDORD

Laredo

vie. 10/31

10:50 pm-11:29 pm

2 stops24h 39m

$258

LaredoChicago

LRD - ORD

LRDORD

Laredo

sáb. 11/1

2:22 pm-9:14 pm

1 stop6h 52m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 15 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 octubre 6, 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
11,040 reviews

Crew

8.0

Food

6.4

Entertainment

6.9

Comfort

7.2

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
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Crew

8.0

Food

6.4

Entertainment

6.9

Comfort

7.2

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 03m. American Airlines provides one of the quickest options available for as low as $273. The distance between Laredo, Texas and Chicago is about 1190 mi.

  • 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 51% 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?

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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 octubre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$204Average$323FlexibilityNo cancel feeOn-time71%

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