Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Laredo, Texas to Chicago from $245

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Laredo, Texas to Chicago departing on 4/25. 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
7:15 am - 12:57 pm
LRD
-
ORD
5h 42m
1 stop
United Airlines Logo
2:10 pm - 8:07 pm
ORD
-
LRD
5h 57m
1 stop
$245United Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
10:24 am - 3:18 pm
LRD
-
ORD
4h 54m
1 stop
American Airlines Logo
5:00 am - 9:54 am
ORD
-
LRD
4h 54m
1 stop
$246American Airlines
Sat, May 9 - Sat, May 16
American Airlines Logo
6:48 pm - 11:48 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
6:04 am - 1:54 pm
ORD
-
LRD
7h 50m
1 stop
$292American Airlines
Tue, Apr 21 - Tue, Apr 28
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
$304American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
6:48 pm - 11:48 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
6:56 pm - 11:58 pm
ORD
-
LRD
5h 02m
1 stop
$335American Airlines
Sat, Apr 25 - Sat, May 2
United Airlines Logo
3:15 pm - 11:15 pm
LRD
-
ORD
8h 00m
1 stop
United Airlines Logo
5:48 am - 11:28 am
ORD
-
LRD
5h 40m
1 stop
$339United Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
2:25 pm - 10:00 pm
LRD
-
ORD
7h 35m
1 stop
American Airlines Logo
6:52 pm - 11:54 pm
ORD
-
LRD
5h 02m
1 stop
$351American Airlines
Sat, Apr 11 - Sat, Nov 7
United Airlines Logo
3:15 pm - 9:31 pm
LRD
-
ORD
6h 16m
1 stop
United Airlines Logo
7:30 am - 2:30 pm
ORD
-
LRD
7h 00m
1 stop
$363United Airlines
Sat, Apr 11 - Tue, Apr 14
American Airlines Logo
6:48 pm - 11:48 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
6:57 am - 1:54 pm
ORD
-
LRD
6h 57m
1 stop
$366American Airlines
Wed, Apr 8 - Sun, Apr 12
United Airlines Logo
5:23 pm - 1:26 am
LRD
-
ORD
8h 03m
1 stop
United Airlines Logo
5:30 am - 11:29 am
ORD
-
LRD
5h 59m
1 stop
$371United Airlines
Thu, Apr 30 - Sun, May 3

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
May 9
LRD10:24 amLaredo
4h 54m
1 stop
ORD3:18 pmChicago O'Hare Intl
May 16
ORD5:00 amChicago O'Hare Intl
4h 54m
1 stop
LRD9:54 amLaredo
$246
American Airlines
Apr 21
LRD6:48 pmLaredo
5h 00m
1 stop
ORD11:48 pmChicago O'Hare Intl
Apr 28
ORD6:04 amChicago O'Hare Intl
7h 50m
1 stop
LRD1:54 pmLaredo
$292
American Airlines
May 12
LRD10:24 amLaredo
7h 20m
1 stop
ORD5:44 pmChicago O'Hare Intl
May 16
ORD12:30 pmChicago O'Hare Intl
5h 47m
1 stop
LRD6:17 pmLaredo
$304

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Apr 25
LRD7:15 amLaredo
5h 42m
1 stop
ORD12:57 pmChicago O'Hare Intl
May 2
ORD2:10 pmChicago O'Hare Intl
5h 57m
1 stop
LRD8:07 pmLaredo
$245
United Airlines
Apr 17
LRD3:15 pmLaredo
8h 00m
1 stop
ORD11:15 pmChicago O'Hare Intl
Apr 21
ORD5:48 amChicago O'Hare Intl
5h 40m
1 stop
LRD11:28 amLaredo
$339
United Airlines
Apr 11
LRD3:15 pmLaredo
6h 16m
1 stop
ORD9:31 pmChicago O'Hare Intl
Apr 14
ORD7:30 amChicago O'Hare Intl
7h 00m
1 stop
LRD2:30 pmLaredo
$363

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 March 29, 2026.
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

Cheapest round-trip

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 4/25

7:15 am-12:57 pm

1 stop5h 42m

Chicago O'Hare Intl

Sat 5/2

2:10 pm-8:07 pm

1 stop5h 57m

$245
Quickest round-trip

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 5/9

10:24 am-3:18 pm

1 stop4h 54m

Chicago O'Hare Intl

Sat 5/16

5:00 am-9:54 am

1 stop4h 54m

$246

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 4/21

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Tue 4/28

6:04 am-1:54 pm

1 stop7h 50m

$292

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 5/12

2:25 pm-10:20 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 5/16

6:56 pm-11:58 pm

1 stop5h 02m

$304

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 4/25

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Sat 5/2

6:56 pm-11:58 pm

1 stop5h 02m

$335

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 4/17

3:15 pm-11:15 pm

1 stop8h 00m

Chicago O'Hare Intl

Tue 4/21

5:48 am-11:28 am

1 stop5h 40m

$339

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 4/11

2:25 pm-10:00 pm

1 stop7h 35m

Chicago O'Hare Intl

Sat 11/7

6:52 pm-11:54 pm

1 stop5h 02m

$351

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 4/11

3:15 pm-9:31 pm

1 stop6h 16m

Chicago O'Hare Intl

Tue 4/14

7:30 am-2:30 pm

1 stop7h 00m

$363

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 4/8

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Sun 4/12

6:57 am-1:54 pm

1 stop6h 57m

$366

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 4/30

5:23 pm-1:26 am

1 stop8h 03m

Chicago O'Hare Intl

Sun 5/3

5:30 am-11:29 am

1 stop5h 59m

$371

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 typical price of a round-trip flight between Laredo, Texas and Chicago?

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 February is your next best option. Flight prices from Laredo, Texas to Chicago during February average around $319.

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 52m

Direct flights

None
The fastest flight from Laredo, Texas to Chicago takes 5h 52m
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 52m, 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
7.1
11,521 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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
Tue 4/28
Tue 5/5
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