ORD - LRD

$245 Find Cheap Flights from Chicago to Laredo - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Laredo departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$245
Overall average: $508
American Airlines
Sat 9/5Sat 9/12
ORD - LRD • 1 stop
Cheapest one-way
$355
American Airlines
Tue 9/8
ORD - LRD • 1 stop
Top airlines
Cheapest • from $245 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Laredo. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $348 (round-trip)
Shortest trip • 5h 47m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 46% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Laredo!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Laredo (ORD-LRD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Laredo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Laredo

Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
2:57 pm - 7:57 pm
ORD
-
LRD
5h 00m
1 stop
American Airlines Logo
6:35 pm - 12:14 am
LRD
-
ORD
5h 39m
1 stop
$245American Airlines
Tue, Sep 22 - Sat, Sep 26
United Airlines Logo
5:30 am - 10:56 am
ORD
-
LRD
5h 26m
1 stop
United Airlines Logo
2:12 pm - 8:05 pm
LRD
-
ORD
5h 53m
1 stop
$255United Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
2:57 pm - 7:57 pm
ORD
-
LRD
5h 00m
1 stop
American Airlines Logo
6:35 pm - 12:14 am
LRD
-
ORD
5h 39m
1 stop
$255American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
8:15 am - 3:23 pm
ORD
-
LRD
7h 08m
1 stop
American Airlines Logo
3:53 pm - 9:09 pm
LRD
-
ORD
5h 16m
1 stop
$255American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
4:50 pm - 10:33 pm
ORD
-
LRD
5h 43m
1 stop
American Airlines Logo
3:53 pm - 9:09 pm
LRD
-
ORD
5h 16m
1 stop
$255American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
9:40 am - 3:23 pm
ORD
-
LRD
5h 43m
1 stop
American Airlines Logo
3:53 pm - 9:09 pm
LRD
-
ORD
5h 16m
1 stop
$256American Airlines
Sat, Sep 5 - Sat, Sep 12
United Airlines Logo
7:30 am - 1:26 pm
ORD
-
LRD
5h 56m
1 stop
United Airlines Logo
2:13 pm - 8:05 pm
LRD
-
ORD
5h 52m
1 stop
$382United Airlines
Tue, Aug 25 - Thu, Sep 3
United Airlines Logo
2:16 pm - 9:16 pm
ORD
-
LRD
7h 00m
1 stop
United Airlines Logo
7:15 am - 12:25 pm
LRD
-
ORD
5h 10m
1 stop
$396United Airlines
Mon, Dec 14 - Sat, Dec 19
United Airlines Logo
5:45 pm - 11:17 pm
ORD
-
LRD
5h 32m
1 stop
United Airlines Logo
5:44 pm - 11:10 pm
LRD
-
ORD
5h 26m
1 stop
$397United Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
6:30 am - 8:18 pm
ORD
-
LRD
13h 48m
2 stops
Multiple Airlines Logo
9:08 pm - 5:38 am
LRD
-
ORD
8h 30m
1 stop
$487Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Laredo flights

Get data-powered insights and trends into flights from Chicago to Laredo to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Laredo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Laredo, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Laredo is August, where tickets cost $204 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $716 and $606 respectively.

Good to know

Low season

July

Cheapest flight

$245
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from Chicago to Laredo

When to book flights from Chicago to Laredo

Are your dates flexible? Find out the best times to travel from Chicago to Laredo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Laredo flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Laredo?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Laredo was $355 for a one-way ticket and $245 for a round-trip.

  • Do I need a passport to fly between Chicago and Laredo?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago to Laredo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Laredo?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Laredo, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Laredo, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Laredo are United Airlines and American Airlines. With an average price for the route of $336 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $291 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Laredo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Laredo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Laredo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Laredo from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Laredo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Laredo with an airline and back to Chicago with another airline. Booking your flights between Chicago and LRD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Laredo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Laredo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Laredo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Laredo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Laredo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10041 reviews
7.7Boarding
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

The SFO lounge closes at 12 midnight. My flight took off at 2AM

8.0 ExcellentAnonymous, Jul 2026
ORD - SFO
Read more United Airlines reviews

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

It isvvery small flight. No leg room . No space to put my personal item at feet.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Everything was awful Flight attendant was condescending, rude and not helpful at all. Small outdated plane. No service, uncomfortable seats. Flight attendant was really the worst. He used hand gestures to communicate instead of words and whenever he used words he was condescending.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

Didn't make it dir to delays - no support from United staff

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

BAD. As a family could not sit together. The gate agent told us there was only one seat in the middle left, when we got on the plane the situation was very different with whole rows of seats empty

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

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

Information on your arrival and departure airports