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Cheap flights from Laredo, Texas to Chicago from $244

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 6/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Laredo, Texas to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:28 pm - 11:36 pm
LRD
-
ORD
5h 08m
1 stop
American Airlines Logo
11:43 am - 6:17 pm
ORD
-
LRD
6h 34m
1 stop
$262American Airlines
Mon, Mar 30 - Tue, Apr 7
American Airlines Logo
6:27 pm - 11:22 pm
LRD
-
ORD
4h 55m
1 stop
American Airlines Logo
11:54 am - 5:54 pm
ORD
-
LRD
6h 00m
1 stop
$265American Airlines
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
6:48 pm - 11:48 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
5:00 am - 9:54 am
ORD
-
LRD
4h 54m
1 stop
$279American Airlines
Thu, Apr 23 - Sun, Apr 26
United Airlines Logo
3:17 pm - 11:08 pm
LRD
-
ORD
7h 51m
1 stop
United Airlines Logo
7:30 am - 2:30 pm
ORD
-
LRD
7h 00m
1 stop
$288United Airlines
Tue, Mar 24 - Tue, Mar 31
American Airlines Logo
6:48 pm - 11:48 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
5:00 am - 9:54 am
ORD
-
LRD
4h 54m
1 stop
$299American Airlines
Thu, Apr 23 - Sun, Apr 26
United Airlines Logo
2:01 pm - 8:05 pm
LRD
-
ORD
6h 04m
1 stop
United Airlines Logo
5:30 am - 1:20 pm
ORD
-
LRD
7h 50m
1 stop
$340United Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:27 pm - 12:03 am
LRD
-
ORD
5h 36m
1 stop
American Airlines Logo
1:26 pm - 5:54 pm
ORD
-
LRD
4h 28m
1 stop
$342American Airlines
Mon, Aug 24 - Sat, Aug 29
United Airlines Logo
2:01 pm - 9:37 pm
LRD
-
ORD
7h 36m
1 stop
United Airlines Logo
6:30 am - 1:20 pm
ORD
-
LRD
6h 50m
1 stop
$349United Airlines
Sat, Aug 22 - Sun, Aug 30
Multiple Airlines Logo
9:37 pm - 6:20 am
LRD
-
ORD
8h 43m
1 stop
Multiple Airlines Logo
7:35 am - 8:47 pm
ORD
-
LRD
13h 12m
2 stops
$355Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
United Airlines Logo
2:01 pm - 9:37 pm
LRD
-
ORD
7h 36m
1 stop
United Airlines Logo
7:30 am - 1:20 pm
ORD
-
LRD
5h 50m
1 stop
$359United Airlines
Sun, Aug 23 - Sun, Aug 30

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Mar 24
LRD3:17 pmLaredo
7h 51m
1 stop
ORD11:08 pmChicago O'Hare Intl
Mar 31
ORD7:30 amChicago O'Hare Intl
7h 00m
1 stop
LRD2:30 pmLaredo
$288
United Airlines
Aug 22
LRD2:01 pmLaredo
6h 04m
1 stop
ORD8:05 pmChicago O'Hare Intl
Aug 29
ORD5:30 amChicago O'Hare Intl
7h 50m
1 stop
LRD1:20 pmLaredo
$340
United Airlines
Aug 22
LRD2:01 pmLaredo
7h 36m
1 stop
ORD9:37 pmChicago O'Hare Intl
Aug 30
ORD6:30 amChicago O'Hare Intl
6h 50m
1 stop
LRD1:20 pmLaredo
$349

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
Mar 30
LRD6:28 pmLaredo
5h 08m
1 stop
ORD11:36 pmChicago O'Hare Intl
Apr 7
ORD11:43 amChicago O'Hare Intl
6h 34m
1 stop
LRD6:17 pmLaredo
$262
American Airlines
Aug 25
LRD6:27 pmLaredo
4h 55m
1 stop
ORD11:22 pmChicago O'Hare Intl
Aug 29
ORD11:54 amChicago O'Hare Intl
6h 00m
1 stop
LRD5:54 pmLaredo
$265
American Airlines
Apr 23
LRD6:48 pmLaredo
5h 00m
1 stop
ORD11:48 pmChicago O'Hare Intl
Apr 26
ORD5:00 amChicago O'Hare Intl
4h 54m
1 stop
LRD9:54 amLaredo
$279

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 4, 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

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 3/30

6:28 pm-11:36 pm

1 stop5h 08m

Chicago O'Hare Intl

Tue 4/7

11:43 am-6:17 pm

1 stop6h 34m

$262

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 8/25

6:27 pm-11:22 pm

1 stop4h 55m

Chicago O'Hare Intl

Sat 8/29

11:54 am-5:54 pm

1 stop6h 00m

$265

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 4/23

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Sun 4/26

5:00 am-9:54 am

1 stop4h 54m

$279

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 3/24

3:17 pm-11:08 pm

1 stop7h 51m

Chicago O'Hare Intl

Tue 3/31

7:30 am-2:30 pm

1 stop7h 00m

$288

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 4/23

6:48 pm-11:48 pm

1 stop5h 00m

Chicago O'Hare Intl

Sun 4/26

5:00 am-9:54 am

1 stop4h 54m

$299

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 8/22

2:01 pm-8:05 pm

1 stop6h 04m

Chicago O'Hare Intl

Sat 8/29

5:30 am-1:20 pm

1 stop7h 50m

$340

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 8/24

6:27 pm-12:03 am

1 stop5h 36m

Chicago O'Hare Intl

Sat 8/29

1:26 pm-5:54 pm

1 stop4h 28m

$342

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 8/22

2:01 pm-9:37 pm

1 stop7h 36m

Chicago O'Hare Intl

Sun 8/30

6:30 am-1:20 pm

1 stop6h 50m

$349

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 4/13

9:37 pm-6:20 am

1 stop8h 43m

Chicago O'Hare Intl

Mon 4/20

7:35 am-8:47 pm

2 stops13h 12m

$355

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sun 8/23

2:01 pm-9:37 pm

1 stop7h 36m

Chicago O'Hare Intl

Sun 8/30

7:30 am-1:20 pm

1 stop5h 50m

$359

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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.

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 16m

Direct flights

None
The fastest flight from Laredo, Texas to Chicago takes 5h 16m
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 16m, 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
11,379 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
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.

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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