$255+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LRD
Sep 19 — Sep 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Laredo with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Laredo
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Cheapest flights from Chicago to LaredoExplore 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 August 20, 2026.
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 August 20, 2026.
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/109:40 am -
1 stop5h 43m
Sat 9/126:35 pm -
1 stop5h 39m
Deal found 8/18![American Airlines logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Tue 9/299:40 am -
1 stop5h 43m
Tue 10/63:49 pm -
1 stop6h 21m
Deal found 8/15![American Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Fri 9/115:00 am -
1 stop5h 05m
Tue 9/156:00 am -
1 stop5h 09m
Deal found 8/17![American Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 11/66:59 am -
1 stop7h 41m
Sun 11/83:53 pm -
1 stop8h 06m
Deal found 8/16![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:30 am -
1 stop8h 07m
Sat 10/242:12 pm -
1 stop5h 52m
Deal found 8/16![United Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:16 pm -
1 stop6h 00m
Wed 9/92:13 pm -
1 stop7h 19m
Deal found 8/15![United Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 9/42:57 pm -
1 stop5h 00m
Mon 9/143:53 pm -
1 stop5h 16m
Deal found 8/16![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/17. 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 8/2510:45 am -
1 stop4h 49m
Sat 8/294:04 pm -
1 stop5h 12m
Deal found 8/17![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/96:30 am -
1 stop6h 56m
Sun 9/132:13 pm -
1 stop7h 19m
Deal found 8/18![United Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 8/289:40 am -
1 stop5h 54m
Mon 9/74:04 pm -
1 stop8h 14m
Deal found 8/16![American Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:34 am -
1 stop6h 40m
Thu 11/195:49 pm -
1 stop6h 56m
Deal found 8/15![United Airlines logo]()
$419
Best flights from Chicago to LaredoDiscover carefully curated flight deals from Chicago to Laredo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
Discover carefully curated flight deals from Chicago to Laredo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 11/66:59 am -
1 stop7h 41m
Sun 11/83:53 pm -
1 stop8h 06m
Deal found 8/20![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:30 am -
1 stop8h 07m
Sat 10/242:12 pm -
1 stop5h 52m
Deal found 8/19![United Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:49 am -
2 stops10h 27m
Sat 9/269:15 am -
1 stop7h 26m
Deal found 8/15![United Airlines logo]()
$480
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:15 am -
1 stop7h 59m
Sun 11/85:49 pm -
2 stops23h 01m
Deal found 8/19![United Airlines logo]()
$497
Last-minute flights from Chicago to LaredoDiscover last-minute flight deals from Chicago to Laredo. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Laredo. Data last updated August 20, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Fri 8/2112:11 pm -
1 stop5h 37m
Wed 8/264:04 pm -
1 stop7h 26m
Deal found 8/15![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 8/17. 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 8/2510:45 am -
1 stop4h 49m
Sat 8/294:04 pm -
1 stop5h 12m
Deal found 8/17![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:16 pm -
1 stop6h 00m
Wed 9/92:13 pm -
1 stop7h 19m
Deal found 8/15![United Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Fri 8/2810:45 am -
1 stop4h 49m
Mon 9/76:18 pm -
1 stop6h 00m
Deal found 8/17![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Fri 9/42:57 pm -
1 stop5h 00m
Mon 9/143:53 pm -
1 stop5h 16m
Deal found 8/17![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/811:00 pm -
2 stops11h 05m
Sat 9/126:35 pm -
1 stop5h 39m
Deal found 8/18![American Airlines logo]()
$460
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/96:30 am -
1 stop6h 56m
Sat 9/1212:30 pm -
1 stop6h 00m
Deal found 8/18![United Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/96:30 am -
1 stop6h 56m
Sun 9/132:13 pm -
1 stop7h 19m
Deal found 8/18![United Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/109:40 am -
1 stop5h 43m
Sat 9/126:35 pm -
1 stop5h 39m
Deal found 8/18![American Airlines logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Fri 9/115:00 am -
1 stop5h 05m
Tue 9/156:00 am -
1 stop5h 09m
Deal found 8/17![American Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Tue 9/299:40 am -
1 stop5h 43m
Tue 10/63:49 pm -
1 stop6h 21m
Deal found 8/15![American Airlines logo]()
$256
One-way flights from Chicago to LaredoSearch for one-way flight options from Chicago to Laredo. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
Search for one-way flight options from Chicago to Laredo. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:47 pm -
1 stop7h 29m
Deal found 8/16![United Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 8/275:00 am -
1 stop5h 12m
Deal found 8/17![American Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 8/17. 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 8/271:30 pm -
2 stops9h 23m
Deal found 8/17![United Airlines logo]()
$622
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 August 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $255 (American Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $365 |
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 7,457,451 searches. Data last updated August 20, 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
Cheapest round-trip
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Fri 11/6
6:59 am-2:40 pm
1 stop7h 41m
Laredo
Sun 11/8
3:53 pm-11:59 pm
1 stop8h 06m
$329
Quickest round-trip
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Wed 10/21
5:30 am-1:37 pm
1 stop8h 07m
Laredo
Sat 10/24
2:12 pm-8:04 pm
1 stop5h 52m
$345
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Sat 9/19
10:49 am-9:16 pm
2 stops10h 27m
Laredo
Sat 9/26
9:15 am-4:41 pm
1 stop7h 26m
$480
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Fri 11/6
9:15 am-5:14 pm
1 stop7h 59m
Laredo
Sun 11/8
5:49 pm-4:50 pm
2 stops23h 01m
$497
Cheapest one-way
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Tue 8/25
12:47 pm-8:16 pm
1 stop7h 29m
$429
Quickest one-way
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Thu 8/27
5:00 am-10:12 am
1 stop5h 12m
$476
ChicagoLaredo
ORD Chicago O'Hare Intl - LRD Laredo
ORDLRD
Chicago O'Hare Intl
Thu 8/27
1:30 pm-10:53 pm
2 stops9h 23m
$622
Sorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
CHI-LRD
ORD-LRD
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
CHI-LRD
ORD-LRD
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?
Airfare is below average for this route at the moment.
Chicago to Laredo, Texas flights typically cost between $323 and $396 in September.The cheapest round-trip price found within the last 5 days was $255 on American Airlines (Sep 10-Sep 12).
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 August 20, 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.
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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.
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Complete your trip
Complete your trip to Laredo by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Chicago to Laredo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Laredo
Explore flights to Laredo departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 20, 2026.
Chicago and Laredo flights
Browse other Chicago and Laredo flight options. Last updated on August 20, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$336 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$243 | Average$291 | FlexibilityNo cancel fee | On-time71% |