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Cheap flights from Laredo, Texas to Chicago from $259

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 12/23. 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.
United Airlines Logo
5:30 pm - 10:37 pmLRD-ORD
5h 07m1 stop
United Airlines Logo
8:54 am - 2:42 pmORD-LRD
5h 48m1 stop
$259United Airlines
Find Deal
Tue, Dec 23 - Wed, Jan 7
American Airlines Logo
6:03 am - 11:55 amLRD-ORD
5h 52m1 stop
American Airlines Logo
3:23 pm - 11:03 pmORD-LRD
7h 40m1 stop
$262American Airlines
Find Deal
Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
6:03 am - 1:55 pmLRD-ORD
7h 52m1 stop
American Airlines Logo
8:10 am - 2:12 pmORD-LRD
6h 02m1 stop
$309American Airlines
Find Deal
Tue, Jan 6 - Tue, Jan 13
American Airlines Logo
6:03 am - 10:54 amLRD-ORD
4h 51m1 stop
American Airlines Logo
1:15 pm - 6:14 pmORD-LRD
4h 59m1 stop
$312American Airlines
Find Deal
Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
12:03 pm - 5:09 pmLRD-ORD
5h 06m1 stop
United Airlines Logo
7:35 am - 1:46 pmORD-LRD
6h 11m1 stop
$339United Airlines
Find Deal
Tue, Apr 21 - Sat, Apr 25
United Airlines Logo
7:15 am - 12:34 pmLRD-ORD
5h 19m1 stop
United Airlines Logo
6:00 am - 11:19 amORD-LRD
5h 19m1 stop
$354United Airlines
Find Deal
Fri, Dec 5 - Wed, Dec 10
United Airlines Logo
5:30 pm - 12:14 amLRD-ORD
6h 44m1 stop
United Airlines Logo
5:49 am - 11:25 amORD-LRD
5h 36m1 stop
$367United Airlines
Find Deal
Tue, Dec 23 - Sun, Jan 4
American Airlines Logo
6:03 am - 10:54 amLRD-ORD
4h 51m1 stop
American Airlines Logo
5:05 am - 10:09 amORD-LRD
5h 04m1 stop
$384American Airlines
Find Deal
Thu, Jan 8 - Thu, Jan 15
United Airlines Logo
5:30 pm - 8:05 amLRD-ORD
14h 35m2 stops
United Airlines Logo
8:54 am - 2:42 pmORD-LRD
5h 48m1 stop
$402United Airlines
Find Deal
Tue, Dec 23 - Wed, Jan 7
American Airlines Logo
6:08 pm - 11:15 pmLRD-ORD
5h 07m1 stop
American Airlines Logo
10:29 am - 5:38 pmORD-LRD
7h 09m1 stop
$414American Airlines
Find Deal
Tue, Dec 23 - Mon, Jan 5

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Dec 23
LRD5:30 pmLaredo
5h 07m
1 stop
ORD10:37 pmChicago O'Hare Intl
Jan 7
ORD8:54 amChicago O'Hare Intl
5h 48m
1 stop
LRD2:42 pmLaredo
$259
Find similar
United Airlines
Apr 21
LRD12:03 pmLaredo
5h 06m
1 stop
ORD5:09 pmChicago O'Hare Intl
Apr 25
ORD7:35 amChicago O'Hare Intl
6h 11m
1 stop
LRD1:46 pmLaredo
$339
Find similar
United Airlines
Dec 5
LRD7:15 amLaredo
5h 19m
1 stop
ORD12:34 pmChicago O'Hare Intl
Dec 10
ORD6:00 amChicago O'Hare Intl
5h 19m
1 stop
LRD11:19 amLaredo
$354
Find similar

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
Jan 7
LRD6:03 amLaredo
5h 52m
1 stop
ORD11:55 amChicago O'Hare Intl
Jan 14
ORD3:23 pmChicago O'Hare Intl
7h 40m
1 stop
LRD11:03 pmLaredo
$262
Find similar
American Airlines
Jan 6
LRD6:03 amLaredo
7h 52m
1 stop
ORD1:55 pmChicago O'Hare Intl
Jan 13
ORD8:10 amChicago O'Hare Intl
6h 02m
1 stop
LRD2:12 pmLaredo
$309
Find similar
American Airlines
Jan 6
LRD6:03 amLaredo
4h 51m
1 stop
ORD10:54 amChicago O'Hare Intl
Jan 13
ORD1:15 pmChicago O'Hare Intl
4h 59m
1 stop
LRD6:14 pmLaredo
$312
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 November 24, 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

Tue 12/23

5:30 pm-10:37 pm

1 stop5h 07m

Chicago O'Hare Intl

Wed 1/7

8:54 am-2:42 pm

1 stop5h 48m

$259

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 1/7

6:03 am-11:55 am

1 stop5h 52m

Chicago O'Hare Intl

Wed 1/14

3:23 pm-11:03 pm

1 stop7h 40m

$262

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 1/6

6:03 am-1:55 pm

1 stop7h 52m

Chicago O'Hare Intl

Tue 1/13

8:10 am-2:12 pm

1 stop6h 02m

$309

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 1/6

6:03 am-10:54 am

1 stop4h 51m

Chicago O'Hare Intl

Tue 1/13

1:15 pm-6:14 pm

1 stop4h 59m

$312

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 4/21

12:03 pm-5:09 pm

1 stop5h 06m

Chicago O'Hare Intl

Sat 4/25

7:35 am-1:46 pm

1 stop6h 11m

$339

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 12/5

7:15 am-12:34 pm

1 stop5h 19m

Chicago O'Hare Intl

Wed 12/10

6:00 am-11:19 am

1 stop5h 19m

$354

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 12/23

5:30 pm-12:14 am

1 stop6h 44m

Chicago O'Hare Intl

Sun 1/4

5:49 am-11:25 am

1 stop5h 36m

$367

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 1/8

6:03 am-10:54 am

1 stop4h 51m

Chicago O'Hare Intl

Thu 1/15

5:05 am-10:09 am

1 stop5h 04m

$384

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 12/23

5:30 pm-8:05 am

2 stops14h 35m

Chicago O'Hare Intl

Wed 1/7

8:54 am-2:42 pm

1 stop5h 48m

$402

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 12/23

6:08 pm-11:15 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 1/5

10:29 am-5:38 pm

1 stop7h 09m

$414

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 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

Direct flights

None
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 4h 51m, 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
11,046 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
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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