Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Laredo, Texas to Chicago from $164

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Laredo, Texas to Chicago departing on 1/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Laredo, Texas to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:17 am - 12:37 pm
LRD
-
ORD
5h 20m1 stop
United Airlines Logo
2:10 pm - 8:02 pm
ORD
-
LRD
5h 52m1 stop
$339United Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
6:08 pm - 11:15 pm
LRD
-
ORD
5h 07m1 stop
American Airlines Logo
6:52 pm - 11:55 pm
ORD
-
LRD
5h 03m1 stop
$407American Airlines
Mon, Dec 22 - Fri, Dec 26
American Airlines Logo
2:22 pm - 7:37 pm
LRD
-
ORD
5h 15m1 stop
American Airlines Logo
10:34 am - 5:38 pm
ORD
-
LRD
7h 04m1 stop
$414American Airlines
Sat, Dec 20 - Mon, Dec 22
United Airlines Logo
3:35 pm - 9:28 pm
LRD
-
ORD
5h 53m1 stop
United Airlines Logo
9:33 pm - 11:26 am
ORD
-
LRD
13h 53m2 stops
$439United Airlines
Sat, Feb 14 - Wed, Feb 18
United Airlines Logo
5:30 pm - 12:14 am
LRD
-
ORD
6h 44m1 stop
United Airlines Logo
5:49 am - 11:25 am
ORD
-
LRD
5h 36m1 stop
$443United Airlines
Thu, Dec 18 - Tue, Dec 23
American Airlines Logo
6:31 pm - 11:43 pm
LRD
-
ORD
5h 12m1 stop
American Airlines Logo
5:00 am - 9:36 am
ORD
-
LRD
4h 36m1 stop
$545American Airlines
Fri, May 22 - Mon, May 25
United Airlines Logo
12:05 pm - 7:55 pm
LRD
-
ORD
7h 50m1 stop
United Airlines Logo
7:48 pm - 11:25 am
ORD
-
LRD
15h 37m2 stops
$581United Airlines
Sat, Dec 20 - Mon, Dec 22
United Airlines Logo
9:50 am - 7:47 am
LRD
-
ORD
21h 57m1 stop
United Airlines Logo
8:12 pm - 7:35 pm
ORD
-
LRD
23h 23m2 stops
$592United Airlines
Fri, May 22 - Mon, May 25
United Airlines Logo
5:30 pm - 10:37 pm
LRD
-
ORD
5h 07m1 stop
United Airlines Logo
7:48 pm - 11:25 am
ORD
-
LRD
15h 37m2 stops
$619United Airlines
Mon, Dec 22 - Fri, Dec 26
United Airlines Logo
7:00 am - 8:05 am
LRD
-
ORD
25h 05m1 stop
United Airlines Logo
10:50 am - 11:17 pm
ORD
-
LRD
12h 27m2 stops
$621United Airlines
Fri, May 22 - Mon, May 25

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
Dec 22
LRD6:08 pmLaredo
5h 07m
1 stop
ORD11:15 pmChicago O'Hare Intl
Dec 26
ORD6:52 pmChicago O'Hare Intl
5h 03m
1 stop
LRD11:55 pmLaredo
$407
Find similar
American Airlines
Dec 20
LRD2:22 pmLaredo
5h 15m
1 stop
ORD7:37 pmChicago O'Hare Intl
Dec 22
ORD10:34 amChicago O'Hare Intl
7h 04m
1 stop
LRD5:38 pmLaredo
$414
Find similar
American Airlines
May 22
LRD6:31 pmLaredo
5h 12m
1 stop
ORD11:43 pmChicago O'Hare Intl
May 25
ORD5:00 amChicago O'Hare Intl
4h 36m
1 stop
LRD9:36 amLaredo
$545
Find similar

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Feb 14
LRD7:17 amLaredo
5h 20m
1 stop
ORD12:37 pmChicago O'Hare Intl
Feb 18
ORD2:10 pmChicago O'Hare Intl
5h 52m
1 stop
LRD8:02 pmLaredo
$339
Find similar
United Airlines
Feb 14
LRD3:35 pmLaredo
5h 53m
1 stop
ORD9:28 pmChicago O'Hare Intl
Feb 18
ORD9:33 pmChicago O'Hare Intl
13h 53m
2 stops
LRD11:26 amLaredo
$439
Find similar
United Airlines
Dec 18
LRD5:30 pmLaredo
6h 44m
1 stop
ORD12:14 amChicago O'Hare Intl
Dec 23
ORD5:49 amChicago O'Hare Intl
5h 36m
1 stop
LRD11:25 amLaredo
$443
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Laredo, Texas to Chicago 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, momondo users made 832,500 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Laredo, Texas to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 2/14

7:17 am-12:37 pm

1 stop5h 20m

Chicago O'Hare Intl

Wed 2/18

2:10 pm-8:02 pm

1 stop5h 52m

$339

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 12/22

6:08 pm-11:15 pm

1 stop5h 07m

Chicago O'Hare Intl

Fri 12/26

6:52 pm-11:55 pm

1 stop5h 03m

$407

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 12/20

2:22 pm-7:37 pm

1 stop5h 15m

Chicago O'Hare Intl

Mon 12/22

10:34 am-5:38 pm

1 stop7h 04m

$414

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 2/14

3:35 pm-9:28 pm

1 stop5h 53m

Chicago O'Hare Intl

Wed 2/18

9:33 pm-11:26 am

2 stops13h 53m

$439

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 12/18

5:30 pm-12:14 am

1 stop6h 44m

Chicago O'Hare Intl

Tue 12/23

5:49 am-11:25 am

1 stop5h 36m

$443

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 5/22

6:31 pm-11:43 pm

1 stop5h 12m

Chicago O'Hare Intl

Mon 5/25

5:00 am-9:36 am

1 stop4h 36m

$545

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 12/20

12:05 pm-7:55 pm

1 stop7h 50m

Chicago O'Hare Intl

Mon 12/22

7:48 pm-11:25 am

2 stops15h 37m

$581

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 5/22

9:50 am-7:47 am

1 stop21h 57m

Chicago O'Hare Intl

Mon 5/25

8:12 pm-7:35 pm

2 stops23h 23m

$592

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 12/22

5:30 pm-10:37 pm

1 stop5h 07m

Chicago O'Hare Intl

Fri 12/26

7:48 pm-11:25 am

2 stops15h 37m

$619

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 5/22

7:00 am-8:05 am

1 stop25h 05m

Chicago O'Hare Intl

Mon 5/25

10:50 am-11:17 pm

2 stops12h 27m

$621

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Laredo, Texas to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Laredo, Texas, with most prices found around $231. If you’re not able to fly to Chicago in August, then May is your next best option. Flight prices from Laredo, Texas to Chicago during May average around $331.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $339. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Laredo, Texas to Chicago for around $451.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Laredo, Texas to Chicago during this time can be as low as $353. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $371.

How have Laredo, Texas to Chicago flight prices changed over time?

When to book flights from Laredo, Texas to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Laredo, Texas to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Laredo, Texas to Chicago (LRD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Laredo, Texas to Chicago

Fastest flight time

5h 20m

Direct flights

None
The fastest flight from Laredo, Texas to Chicago takes 5h 20m
There are no direct flights from Laredo, Texas to Chicago. There are no popular flight routes from Laredo, Texas to Chicago.
Search flight deals

  • How far is Laredo to Chicago by plane?

    A flight from Laredo to Chicago will travel around 1197.0 mi. Flights usually cover this in 5h 07m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Laredo Airport to Chicago?

    Prices for flights from Laredo Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Laredo Airport to Chicago?

  • How old do you have to be to fly from Laredo Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Laredo Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Laredo, Texas to Chicago?

Best airlines flying from Laredo, Texas to Chicago

Compare and see reviews for airlines that fly from Laredo, Texas to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $204Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Laredo to Chicago?

Finding the right flight to Chicago from Laredo is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Laredo to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Laredo with this policy.

How can momondo help me find flights from Laredo to Chicago?

momondo helps you find the best flight between Laredo and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Laredo to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Laredo to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 1/7
Wed 1/14
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport