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Cheap flights from Laredo, Texas to Chicago from $188

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 8/16. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
6:18 pm - 11:30 pm
LRD
-
ORD
5h 12m
1 stop
American Airlines Logo
5:00 am - 10:12 am
ORD
-
LRD
5h 12m
1 stop
$245American Airlines
Sat, Aug 22 - Sat, Aug 29
United Airlines Logo
2:09 pm - 7:52 pm
LRD
-
ORD
5h 43m
1 stop
United Airlines Logo
6:00 am - 11:12 am
ORD
-
LRD
5h 12m
1 stop
$282United Airlines
Thu, Dec 24 - Wed, Jan 6
American Airlines Logo
6:18 pm - 12:18 am
LRD
-
ORD
6h 00m
1 stop
American Airlines Logo
2:57 pm - 7:57 pm
ORD
-
LRD
5h 00m
1 stop
$319American Airlines
Wed, Aug 5 - Wed, Aug 12
United Airlines Logo
9:15 am - 4:41 pm
LRD
-
ORD
7h 26m
1 stop
United Airlines Logo
6:25 am - 1:37 pm
ORD
-
LRD
7h 12m
1 stop
$335United Airlines
Tue, Sep 29 - Wed, Oct 7
American Airlines Logo
6:18 pm - 12:18 am
LRD
-
ORD
6h 00m
1 stop
American Airlines Logo
2:57 pm - 7:57 pm
ORD
-
LRD
5h 00m
1 stop
$341American Airlines
Wed, Aug 5 - Wed, Aug 12
United Airlines Logo
2:13 pm - 9:32 pm
LRD
-
ORD
7h 19m
1 stop
United Airlines Logo
6:30 am - 1:26 pm
ORD
-
LRD
6h 56m
1 stop
$359United Airlines
Sat, Aug 22 - Mon, Aug 31
American Airlines Logo
6:35 pm - 12:14 am
LRD
-
ORD
5h 39m
1 stop
American Airlines Logo
8:15 am - 3:19 pm
ORD
-
LRD
7h 04m
1 stop
$372American Airlines
Fri, Oct 2 - Wed, Oct 7
United Airlines Logo
5:42 pm - 11:26 pm
LRD
-
ORD
5h 44m
1 stop
United Airlines Logo
6:00 am - 1:31 pm
ORD
-
LRD
7h 31m
1 stop
$377United Airlines
Wed, Nov 18 - Sat, Nov 21
United Airlines Logo
5:42 pm - 11:26 pm
LRD
-
ORD
5h 44m
1 stop
United Airlines Logo
4:00 pm - 9:31 pm
ORD
-
LRD
5h 31m
1 stop
$379United Airlines
Wed, Nov 18 - Sat, Nov 21
United Airlines Logo
2:06 pm - 8:05 pm
LRD
-
ORD
5h 59m
1 stop
United Airlines Logo
5:30 am - 1:31 pm
ORD
-
LRD
8h 01m
1 stop
$387United Airlines
Wed, Aug 5 - Sun, Aug 9

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United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Dec 24
LRD2:09 pmLaredo
5h 43m
1 stop
ORD7:52 pmChicago O'Hare Intl
Jan 6
ORD6:00 amChicago O'Hare Intl
5h 12m
1 stop
LRD11:12 amLaredo
$282
United Airlines
Sep 29
LRD9:15 amLaredo
7h 26m
1 stop
ORD4:41 pmChicago O'Hare Intl
Oct 7
ORD6:25 amChicago O'Hare Intl
7h 12m
1 stop
LRD1:37 pmLaredo
$335
United Airlines
Aug 22
LRD2:13 pmLaredo
7h 19m
1 stop
ORD9:32 pmChicago O'Hare Intl
Aug 31
ORD6:30 amChicago O'Hare Intl
6h 56m
1 stop
LRD1:26 pmLaredo
$359

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
Aug 22
LRD6:18 pmLaredo
5h 12m
1 stop
ORD11:30 pmChicago O'Hare Intl
Aug 29
ORD5:00 amChicago O'Hare Intl
5h 12m
1 stop
LRD10:12 amLaredo
$245
American Airlines
Aug 5
LRD6:18 pmLaredo
6h 00m
1 stop
ORD12:18 amChicago O'Hare Intl
Aug 12
ORD2:57 pmChicago O'Hare Intl
5h 00m
1 stop
LRD7:57 pmLaredo
$319
American Airlines
Aug 5
LRD6:18 pmLaredo
6h 00m
1 stop
ORD12:18 amChicago O'Hare Intl
Aug 12
ORD2:57 pmChicago O'Hare Intl
5h 00m
1 stop
LRD7:57 pmLaredo
$341

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 July 18, 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
Quickest round-trip

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 8/22

6:18 pm-11:30 pm

1 stop5h 12m

Chicago O'Hare Intl

Sat 8/29

5:00 am-10:12 am

1 stop5h 12m

$245

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 12/24

2:09 pm-7:52 pm

1 stop5h 43m

Chicago O'Hare Intl

Wed 1/6

6:00 am-11:12 am

1 stop5h 12m

$282

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 8/5

6:18 pm-12:18 am

1 stop6h 00m

Chicago O'Hare Intl

Wed 8/12

2:57 pm-7:57 pm

1 stop5h 00m

$319

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 9/29

9:15 am-4:41 pm

1 stop7h 26m

Chicago O'Hare Intl

Wed 10/7

6:25 am-1:37 pm

1 stop7h 12m

$335

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 8/5

6:18 pm-12:18 am

1 stop6h 00m

Chicago O'Hare Intl

Wed 8/12

2:57 pm-7:57 pm

1 stop5h 00m

$341

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 8/22

2:13 pm-9:32 pm

1 stop7h 19m

Chicago O'Hare Intl

Mon 8/31

6:30 am-1:26 pm

1 stop6h 56m

$359

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 10/2

6:35 pm-12:14 am

1 stop5h 39m

Chicago O'Hare Intl

Wed 10/7

8:15 am-3:19 pm

1 stop7h 04m

$372

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 11/18

5:42 pm-11:26 pm

1 stop5h 44m

Chicago O'Hare Intl

Sat 11/21

6:00 am-1:31 pm

1 stop7h 31m

$377

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 11/18

5:42 pm-11:26 pm

1 stop5h 44m

Chicago O'Hare Intl

Sat 11/21

4:00 pm-9:31 pm

1 stop5h 31m

$379

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 8/5

2:06 pm-8:05 pm

1 stop5h 59m

Chicago O'Hare Intl

Sun 8/9

5:30 am-1:31 pm

1 stop8h 01m

$387

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 typical price of a round-trip flight between Laredo, Texas and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Laredo, Texas, with most prices found around $319. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Laredo, Texas to Chicago during January average around $344.

Can stopping save me money on Laredo, Texas to Chicago flights?

You could potentially save up to 23% on your flight if you consider stops on a Laredo, Texas to Chicago flight.

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 43m

Direct flights

None
The fastest flight from Laredo, Texas to Chicago takes 5h 43m
There are no direct flights from Laredo, Texas to Chicago. There are no popular flight routes from Laredo, Texas to Chicago.
Search flight deals

Frequently asked questions about flying from Laredo, Texas to Chicago

  • 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 43m, 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
United AirlinesPriceFrom $284Free CancellationRating
7.4
10,006 reviews
Search United 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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