LRD - ORD

$299 Find Cheap Flights from Laredo to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Laredo to Chicago departing on 5/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Laredo to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Laredo to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$304
American Airlines
Wed 7/8Tue 7/14
LRD - ORD • 1 stop
Cheapest one-way
$227
Multiple Airlines
Fri 5/8
LRD - ORD • 2 stops
Top airlines
Cheapest • from $304 (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 Laredo and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $319 (round-trip)
Shortest trip • 4h 55m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Laredo to Chicago (LRD-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Laredo to Chicago 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 Laredo to Chicago

Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
6:53 pm - 12:43 am
LRD
-
ORD
5h 50m
1 stop
American Airlines Logo
12:05 pm - 6:21 pm
ORD
-
LRD
6h 16m
1 stop
$304American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
6:32 pm - 12:42 am
LRD
-
ORD
6h 10m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$339American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
2:25 pm - 9:45 pm
LRD
-
ORD
7h 20m
1 stop
American Airlines Logo
5:00 am - 9:54 am
ORD
-
LRD
4h 54m
1 stop
$351American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
6:32 pm - 12:42 am
LRD
-
ORD
6h 10m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$353American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
6:32 pm - 12:42 am
LRD
-
ORD
6h 10m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$354American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
2:25 pm - 10:20 pm
LRD
-
ORD
7h 55m
1 stop
American Airlines Logo
6:56 pm - 11:58 pm
ORD
-
LRD
5h 02m
1 stop
$363American Airlines
Wed, Jul 1 - Sat, Jul 11
American Airlines Logo
6:32 pm - 12:39 am
LRD
-
ORD
6h 07m
1 stop
American Airlines Logo
12:05 pm - 7:38 pm
ORD
-
LRD
7h 33m
1 stop
$397American Airlines
Fri, Jun 12 - Fri, Jun 19
American Airlines Logo
6:32 pm - 12:39 am
LRD
-
ORD
6h 07m
1 stop
American Airlines Logo
8:19 am - 3:04 pm
ORD
-
LRD
6h 45m
1 stop
$424American Airlines
Fri, Jun 12 - Fri, Jun 19
American Airlines Logo
6:32 pm - 12:39 am
LRD
-
ORD
6h 07m
1 stop
American Airlines Logo
6:20 pm - 12:08 am
ORD
-
LRD
5h 48m
1 stop
$425American Airlines
Thu, Jun 11 - Thu, Jun 18
American Airlines Logo
3:34 pm - 9:00 pm
LRD
-
ORD
5h 26m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$442American Airlines
Booking Insights

KAYAK's insights & trends for Laredo to Chicago flights

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

Which airlines provide the cheapest flights from Laredo to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Laredo to Chicago were found on American Airlines ($304) and United Airlines ($496).

Good to know

Cheapest flight$227
Flight from Laredo to Chicago

When to book flights from Laredo to Chicago

Are your dates flexible? Find out the best times to travel from Laredo to Chicago 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 Laredo to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Laredo to Chicago O'Hare Intl Airport was $227 for a one-way ticket and $304 for a round-trip.

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

    No, a passport isn't needed to fly from Laredo to Chicago. However, local authorities might ask for an official ID.

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

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

  • Which airline alliances offer flights from Laredo to Chicago?

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

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

    The two airlines most popular with KAYAK users for flights from Laredo to Chicago are United Airlines and American Airlines. With an average price for the route of $387 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 $323 and an overall rating of 7.1.

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

    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 Laredo to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Laredo 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 Laredo to Chicago?

    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 Chicago with an airline and back to Laredo with another airline. Booking your flights between Laredo and ORD 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 Laredo to Chicago?

    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 Chicago from Laredo 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 Laredo to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Laredo to Chicago. 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 Laredo to Chicago? 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 9677 reviews
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
7.1Entertainment
Airline reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports