LRD - ORD

$244 Find Cheap Flights from Laredo to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Laredo to Chicago departing on 7/3. 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
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Everything you should know

Cheapest round-trip
$244
American Airlines
Fri 7/3Sat 7/11
LRD - ORD • 1 stop
Cheapest one-way
$309
American Airlines
Tue 6/30
LRD - ORD • 1 stop
Top airlines
American Airlines
Cheapest • from $244 (round-trip)
United Airlines
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
Dallas (DFW)
Cheapest • Avg $334 (round-trip)
Dallas (DFW)
Shortest trip • 4h 59m (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

Fri, Jul 3 - Sat, Jul 11
American Airlines Logo
6:53 pm - 12:50 am
LRD
-
ORD
5h 57m
1 stop
American Airlines Logo
5:00 am - 10:01 am
ORD
-
LRD
5h 01m
1 stop
$244American Airlines
Sat, Jul 11 - Wed, Jul 15
American Airlines Logo
6:52 pm - 12:50 am
LRD
-
ORD
5h 58m
1 stop
American Airlines Logo
5:00 am - 10:01 am
ORD
-
LRD
5h 01m
1 stop
$245American Airlines
Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
6:18 pm - 12:18 am
LRD
-
ORD
6h 00m
1 stop
American Airlines Logo
5:00 am - 10:05 am
ORD
-
LRD
5h 05m
1 stop
$246American Airlines
Tue, Jul 7 - Tue, Jul 28
American Airlines Logo
6:53 pm - 12:50 am
LRD
-
ORD
5h 57m
1 stop
American Airlines Logo
5:00 am - 10:01 am
ORD
-
LRD
5h 01m
1 stop
$287American Airlines
Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
6:00 am - 11:11 am
LRD
-
ORD
5h 11m
1 stop
American Airlines Logo
5:00 am - 10:05 am
ORD
-
LRD
5h 05m
1 stop
$288American Airlines
Sat, Jun 27 - Sat, Jul 11
American Airlines Logo
6:44 pm - 12:39 am
LRD
-
ORD
5h 55m
1 stop
American Airlines Logo
5:00 am - 10:01 am
ORD
-
LRD
5h 01m
1 stop
$304American Airlines
Sat, Jun 20 - Wed, Jul 1
United Airlines Logo
7:15 am - 12:29 pm
LRD
-
ORD
5h 14m
1 stop
United Airlines Logo
6:29 am - 1:31 pm
ORD
-
LRD
7h 02m
1 stop
$328United Airlines
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
2:13 pm - 9:32 pm
LRD
-
ORD
7h 19m
1 stop
United Airlines Logo
5:30 am - 10:56 am
ORD
-
LRD
5h 26m
1 stop
$335United Airlines
Wed, Jun 24 - Wed, Jul 1
American Airlines Logo
3:34 pm - 11:32 pm
LRD
-
ORD
7h 58m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$341American Airlines
Wed, Jun 24 - Wed, Jul 1
American Airlines Logo
6:32 pm - 11:32 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$346American 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 5 days.

In the past 5 days, the cheapest round-trip tickets from Laredo to Chicago were found on American Airlines ($244) and United Airlines ($328).

Find deals

Good to know

Cheapest flight$244
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 5 days, the lowest price for a flight from Laredo to Chicago O'Hare Intl Airport was $309 for a one-way ticket and $244 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 is the only airline alliance operating flights between Laredo and Chicago.

  • 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 airline 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 9805 reviews
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

Boarded early, left early, arrived 40 mins early! A win win for me!

10.0 ExcellentJanice, Jun 2026
IAH - ORD
Read more United Airlines reviews

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

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.

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

Information on your arrival and departure airports

Laredo (LRD)
O'Hare Intl (ORD)