What are the cheapest airlines flying 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 $206 on this airline. An additional option worth looking into is United Airlines, starting at $339. American Airlines is currently priced 53% below the average price you’ll pay for this route.

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.

What is the cheapest day to fly from Laredo, Texas to Chicago?

Travelers seeking maximum savings on their Laredo, Texas to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What is the cheapest day to fly round-trip from Laredo, Texas to Chicago?

Flying to your destination on a Wednesday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

What is the cheapest month to fly from Laredo, Texas to Chicago?

July can be a great time to fly to Chicago from Laredo, Texas with a flight ticket averaging about $448. Cheapflights users have found deals in the month of July for as cheap as $232. The most expensive prices can be found in the month of February.

What is the cheapest time of day to fly from LRD to CHI?

One of the essential ways to save on airfare from Laredo, Texas to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 5% on airfare.

Most accurate provider : When it comes to deals on Laredo, Texas-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Laredo, Texas-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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.

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.

$206+ Flights from Laredo, TX to Chicago - Compare & Save Big

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Cheap flight deals from Laredo to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$206 (American Airlines)
Popular in	February
Cheapest in	July
Average price	$343

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

Highest demand for flights based on searches. 32% potential increase in price ($214 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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 April 29, 2025.

Sat 5/246:29 pmLRD - ORD

1 stop5h 27mAmerican Airlines

Sat 5/3112:09 pmORD - LRD

1 stop5h 50mAmerican Airlines

Deal found 4/29

$206

Sun 9/215:24 pmLRD - ORD

1 stop5h 17mUnited Airlines

Sun 9/286:00 amORD - LRD

1 stop5h 02mUnited Airlines

Deal found 4/28

$339

Best flights from Laredo to Chicago
Discover carefully curated flight deals from Laredo to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2025.

Sat 5/246:29 pmLRD - ORD

1 stop5h 27mAmerican Airlines

Sat 5/3112:09 pmORD - LRD

1 stop5h 50mAmerican Airlines

Deal found 4/29

$206

Sun 9/215:24 pmLRD - ORD

1 stop5h 17mUnited Airlines

Sun 9/286:00 amORD - LRD

1 stop5h 02mUnited Airlines

Deal found 4/28

$339

Last-minute flights from Laredo to Chicago
Discover last-minute flight deals from Laredo to Chicago. Data last updated April 29, 2025 and is based on user searches.

Fri 5/92:19 pmLRD - ORD

1 stop6h 49mAmerican Airlines

Mon 5/124:45 pmORD - LRD

1 stop7h 10mAmerican Airlines

Deal found 4/29

$369

Fri 5/92:01 pmLRD - ORD

1 stop7h 29mUnited Airlines

Mon 5/129:00 amORD - LRD

2 stops13h 00mUnited Airlines

Deal found 4/29

$577

Thu 5/155:25 pmLRD - ORD

1 stop6h 50mUnited Airlines

Mon 5/198:00 pmORD - LRD

2 stops17h 26mUnited Airlines

Deal found 4/29

$468

Sat 5/246:29 pmLRD - ORD

1 stop5h 27mAmerican Airlines

Sat 5/3112:09 pmORD - LRD

1 stop5h 50mAmerican Airlines

Deal found 4/29

$206

One-way flights from Laredo to Chicago
Search for one-way flight options from Laredo to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2025.

Thu 6/125:55 amLRD - ORD

1 stop7h 25mAmerican Airlines

Deal found 4/28

$230

Sun 6/295:25 pmLRD - ORD

2 stops16h 24mUnited Airlines

Deal found 4/28

$354

Cheapflights Fare Finder

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

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 5/24

6:29 pm-11:56 pm

1 stop5h 27m

Chicago O'Hare Intl

Sat 5/31

12:09 pm-5:59 pm

1 stop5h 50m

$206

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sun 9/21

5:24 pm-10:41 pm

1 stop5h 17m

Chicago O'Hare Intl

Sun 9/28

6:00 am-11:02 am

1 stop5h 02m

$339

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 6/12

5:55 am-1:20 pm

1 stop7h 25m

$230

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sun 6/29

5:25 pm-9:49 am

2 stops16h 24m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Compare providers for flights from Laredo to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Laredo to Chicago in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Laredo, Texas-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with United Airlines and American Airlines from Laredo to Chicago to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

United Airlines

7.4

Good

8,696 reviews

Reviews

1 / 20

2.0

Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

United Airlines

7.4

Good

8,696 reviews

United Airlines

7.4

Good

8,696 reviews

Reviews

1 / 20

2.0

Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

American Airlines

7.2

Good

10,000 reviews

United Airlines

7.4

Good

8,696 reviews

Reviews

1 / 20

2.0

Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

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 are the cheapest airlines flying 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 $206 on this airline. An additional option worth looking into is United Airlines, starting at $339. American Airlines is currently priced 53% 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

Merrillville

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Porter

Lansing

Valparaiso

Chesterton

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Top airline flying from Laredo to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$207	Average$333	FlexibilityNo cancel fee	On-time71%

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$206+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Laredo to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Laredo to Chicago

Most accurate provider

Most trusted provider

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Laredo to Chicago

Cheapest flights from Laredo to ChicagoExplore 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 April 29, 2025.

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 April 29, 2025.

Cheapflights Fare Finder

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

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 April.

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.

Cheapflights Insights

Everything you need to know about your flight from Laredo to Chicago

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with United Airlines and American Airlines from Laredo to Chicago to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

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

Can I find deals for flights from Laredo to Chicago that include hotel bookings?

How can I find direct flights from Laredo to Chicago?

Can I find deals for business class flights from Laredo to Chicago?

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

Traveling to a place near Laredo?

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Alternative routes for Laredo to Chicago

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Top airline flying from Laredo to Chicago

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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 April 29, 2025.