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Cheap flights from Laredo, Texas to Chicago from $165

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 12/8. 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

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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
6:45 pm - 11:44 pmLRD-ORD
4h 59m1 stop
American Airlines Logo
6:54 am - 2:12 pmORD-LRD
7h 18m1 stop
$232American Airlines
Find Deal
Mon, Jan 12 - Sat, Jan 17
United Airlines Logo
12:05 pm - 7:49 pmLRD-ORD
7h 44m1 stop
United Airlines Logo
5:37 am - 11:28 amORD-LRD
5h 51m1 stop
$259United Airlines
Find Deal
Wed, Jan 7 - Sat, Jan 10
American Airlines Logo
10:39 am - 5:09 pmLRD-ORD
6h 30m1 stop
American Airlines Logo
11:56 am - 6:14 pmORD-LRD
6h 18m1 stop
$355American Airlines
Find Deal
Thu, Jan 8 - Tue, Jan 13
United Airlines Logo
7:15 am - 2:40 pmLRD-ORD
7h 25m1 stop
United Airlines Logo
7:50 pm - 11:28 amORD-LRD
15h 38m2 stops
$412United Airlines
Find Deal
Mon, Jan 12 - Sat, Jan 17
American Airlines Logo
5:38 am - 10:54 amLRD-ORD
5h 16m1 stop
American Airlines Logo
7:36 am - 1:52 pmORD-LRD
6h 16m1 stop
$414American Airlines
Find Deal
Mon, Dec 29 - Sat, Jan 3
United Airlines Logo
7:15 am - 6:25 pmLRD-ORD
11h 10m2 stops
United Airlines Logo
5:37 am - 11:28 amORD-LRD
5h 51m1 stop
$423United Airlines
Find Deal
Wed, Jan 7 - Sat, Jan 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
$430United Airlines
Find Deal
Fri, Dec 19 - Sun, Dec 21
United Airlines Logo
7:15 am - 6:26 pmLRD-ORD
11h 11m2 stops
United Airlines Logo
5:40 am - 11:28 amORD-LRD
5h 48m1 stop
$432United Airlines
Find Deal
Thu, Jan 8 - Tue, Jan 13
United Airlines Logo
5:30 pm - 12:14 amLRD-ORD
6h 44m1 stop
United Airlines Logo
4:00 pm - 9:41 pmORD-LRD
5h 41m1 stop
$438United Airlines
Find Deal
Fri, Dec 19 - Mon, Dec 22
Multiple Airlines Logo
11:45 am - 5:32 amLRD-ORD
17h 47m1 stop
Multiple Airlines Logo
9:14 pm - 5:07 pmORD-LRD
19h 53m2 stops
$465Multiple Airlines
Find Deal
Sun, Nov 30 - Thu, Dec 4

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Jan 7
LRD12:05 pmLaredo
7h 44m
1 stop
ORD7:49 pmChicago O'Hare Intl
Jan 10
ORD5:37 amChicago O'Hare Intl
5h 51m
1 stop
LRD11:28 amLaredo
$259
Find similar
United Airlines
Nov 21
LRD5:22 pmLaredo
5h 48m
1 stop
ORD11:10 pmChicago O'Hare Intl
Nov 28
ORD6:00 amChicago O'Hare Intl
5h 18m
1 stop
LRD11:18 amLaredo
$409
Find similar
United Airlines
Jan 12
LRD7:15 amLaredo
7h 25m
1 stop
ORD2:40 pmChicago O'Hare Intl
Jan 17
ORD7:50 pmChicago O'Hare Intl
15h 38m
2 stops
LRD11:28 amLaredo
$412
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 12
LRD6:45 pmLaredo
4h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jan 17
ORD6:54 amChicago O'Hare Intl
7h 18m
1 stop
LRD2:12 pmLaredo
$232
Find similar
American Airlines
Jan 8
LRD10:39 amLaredo
6h 30m
1 stop
ORD5:09 pmChicago O'Hare Intl
Jan 13
ORD11:56 amChicago O'Hare Intl
6h 18m
1 stop
LRD6:14 pmLaredo
$355
Find similar
American Airlines
Dec 29
LRD5:38 amLaredo
5h 16m
1 stop
ORD10:54 amChicago O'Hare Intl
Jan 3
ORD7:36 amChicago O'Hare Intl
6h 16m
1 stop
LRD1:52 pmLaredo
$414
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 17, 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

Mon 1/12

6:45 pm-11:44 pm

1 stop4h 59m

Chicago O'Hare Intl

Sat 1/17

6:54 am-2:12 pm

1 stop7h 18m

$232

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 1/7

12:05 pm-7:49 pm

1 stop7h 44m

Chicago O'Hare Intl

Sat 1/10

5:37 am-11:28 am

1 stop5h 51m

$259

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 1/8

10:39 am-5:09 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 1/13

11:56 am-6:14 pm

1 stop6h 18m

$355

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 1/12

7:15 am-2:40 pm

1 stop7h 25m

Chicago O'Hare Intl

Sat 1/17

7:50 pm-11:28 am

2 stops15h 38m

$412

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 12/29

5:38 am-10:54 am

1 stop5h 16m

Chicago O'Hare Intl

Sat 1/3

7:36 am-1:52 pm

1 stop6h 16m

$414

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 1/7

7:15 am-6:25 pm

2 stops11h 10m

Chicago O'Hare Intl

Sat 1/10

5:37 am-11:28 am

1 stop5h 51m

$423

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 12/19

5:30 pm-12:14 am

1 stop6h 44m

Chicago O'Hare Intl

Sun 12/21

5:49 am-11:25 am

1 stop5h 36m

$430

LaredoChicago

LRD - ORD

LRDORD

Laredo

Thu 1/8

7:15 am-6:26 pm

2 stops11h 11m

Chicago O'Hare Intl

Tue 1/13

5:40 am-11:28 am

1 stop5h 48m

$432

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 12/19

5:30 pm-12:14 am

1 stop6h 44m

Chicago O'Hare Intl

Mon 12/22

4:00 pm-9:41 pm

1 stop5h 41m

$438

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sun 11/30

11:45 am-5:32 am

1 stop17h 47m

Chicago O'Hare Intl

Thu 12/4

9:14 pm-5:07 pm

2 stops19h 53m

$465

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 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 59m, 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
11,048 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.

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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