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Cheap flights from Laredo, Texas to Chicago from $204

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 11/1. 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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Find the cheapest flights from Laredo, Texas to Chicago

Cheap round-trip flights

American Airlines Logo
6:39 pm - 11:42 pmLRD-ORD
5h 03m1 stop
American Airlines Logo
11:46 am - 6:12 pmORD-LRD
6h 26m1 stop
$204American Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
6:39 pm - 11:42 pmLRD-ORD
5h 03m1 stop
American Airlines Logo
11:46 am - 6:12 pmORD-LRD
6h 26m1 stop
$205American Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
2:18 pm - 9:45 pmLRD-ORD
7h 27m1 stop
American Airlines Logo
4:18 pm - 10:51 pmORD-LRD
6h 33m1 stop
$245American Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
United Airlines Logo
5:15 pm - 10:41 pmLRD-ORD
5h 26m1 stop
United Airlines Logo
6:00 am - 11:02 amORD-LRD
5h 02m1 stop
$316United Airlines
Find Deal
Wed, Aug 27 - Sun, Aug 31
American Airlines Logo
5:58 am - 12:05 pmLRD-ORD
6h 07m1 stop
American Airlines Logo
8:05 am - 4:08 pmORD-LRD
8h 03m1 stop
$336American Airlines
Find Deal
Tue, Dec 9 - Mon, Dec 15
Logo
10:41 pm - 11:51 amLRD-ORD
13h 10m1 stop
Logo
6:15 am - 10:00 pmORD-LRD
15h 45m1 stop
$337
Find Deal
Fri, Sep 26 - Fri, Oct 3
Logo
10:41 pm - 7:50 pmLRD-ORD
21h 09m2 stops
Logo
9:00 am - 10:00 pmORD-LRD
13h 00m1 stop
$354
Find Deal
Fri, Sep 26 - Fri, Oct 3
United Airlines Logo
7:15 am - 12:23 pmLRD-ORD
5h 08m1 stop
United Airlines Logo
9:00 am - 4:09 pmORD-LRD
7h 09m1 stop
$363United Airlines
Find Deal
Tue, Aug 26 - Sat, Aug 30
United Airlines Logo
7:10 am - 12:17 pmLRD-ORD
5h 07m1 stop
United Airlines Logo
2:23 pm - 4:08 pmORD-LRD
25h 45m2 stops
$364United Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
United Airlines Logo
7:00 am - 6:50 pmLRD-ORD
11h 50m2 stops
United Airlines Logo
12:45 pm - 7:56 pmORD-LRD
7h 11m1 stop
$365United Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
Nov 1
LRD6:39 pmLaredo
5h 03m
1 stop
ORD11:42 pmChicago O'Hare Intl
Nov 5
ORD11:46 amChicago O'Hare Intl
6h 26m
1 stop
LRD6:12 pmLaredo
$204
Find similar
American Airlines
Nov 1
LRD6:39 pmLaredo
5h 03m
1 stop
ORD11:42 pmChicago O'Hare Intl
Nov 5
ORD11:46 amChicago O'Hare Intl
6h 26m
1 stop
LRD6:12 pmLaredo
$205
Find similar
American Airlines
Sep 27
LRD2:18 pmLaredo
7h 27m
1 stop
ORD9:45 pmChicago O'Hare Intl
Oct 4
ORD4:18 pmChicago O'Hare Intl
6h 33m
1 stop
LRD10:51 pmLaredo
$245
Find similar

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Aug 27
LRD5:15 pmLaredo
5h 26m
1 stop
ORD10:41 pmChicago O'Hare Intl
Aug 31
ORD6:00 amChicago O'Hare Intl
5h 02m
1 stop
LRD11:02 amLaredo
$316
Find similar
United Airlines
Aug 26
LRD7:15 amLaredo
5h 08m
1 stop
ORD12:23 pmChicago O'Hare Intl
Aug 30
ORD9:00 amChicago O'Hare Intl
7h 09m
1 stop
LRD4:09 pmLaredo
$363
Find similar
United Airlines
Nov 1
LRD7:10 amLaredo
5h 07m
1 stop
ORD12:17 pmChicago O'Hare Intl
Nov 5
ORD2:23 pmChicago O'Hare Intl
25h 45m
2 stops
LRD4:08 pmLaredo
$364
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 August 14, 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

Sat 11/1

6:39 pm-11:42 pm

1 stop5h 03m

Chicago O'Hare Intl

Wed 11/5

11:46 am-6:12 pm

1 stop6h 26m

$204

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 11/1

6:39 pm-11:42 pm

1 stop5h 03m

Chicago O'Hare Intl

Wed 11/5

11:46 am-6:12 pm

1 stop6h 26m

$205

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 9/27

2:18 pm-9:45 pm

1 stop7h 27m

Chicago O'Hare Intl

Sat 10/4

4:18 pm-10:51 pm

1 stop6h 33m

$245

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 8/27

5:15 pm-10:41 pm

1 stop5h 26m

Chicago O'Hare Intl

Sun 8/31

6:00 am-11:02 am

1 stop5h 02m

$316

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 12/9

5:58 am-12:05 pm

1 stop6h 07m

Chicago O'Hare Intl

Mon 12/15

8:05 am-4:08 pm

1 stop8h 03m

$336

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 9/26

10:41 pm-11:51 am

1 stop13h 10m

Chicago O'Hare Intl

Fri 10/3

6:15 am-10:00 pm

1 stop15h 45m

$337

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 9/26

10:41 pm-7:50 pm

2 stops21h 09m

Chicago O'Hare Intl

Fri 10/3

9:00 am-10:00 pm

1 stop13h 00m

$354

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 8/26

7:15 am-12:23 pm

1 stop5h 08m

Chicago O'Hare Intl

Sat 8/30

9:00 am-4:09 pm

1 stop7h 09m

$363

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 11/1

7:10 am-12:17 pm

1 stop5h 07m

Chicago O'Hare Intl

Wed 11/5

2:23 pm-4:08 pm

2 stops25h 45m

$364

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 9/27

7:00 am-6:50 pm

2 stops11h 50m

Chicago O'Hare Intl

Sat 10/4

12:45 pm-7:56 pm

1 stop7h 11m

$365

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 November is, on average, the cheapest month to fly to Chicago from Laredo, Texas, with most prices found around $283. If you’re not able to fly to Chicago in November, then April is your next best option. Flight prices from Laredo, Texas to Chicago during April 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?

As of August 2025, prices for Laredo, Texas to Chicago flights are approximately 4% more expensive when compared to flights at the same time last year.

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

Best Price Found

$204

Fastest flight time

4h 57m

Direct flights

None

Airports in Chicago

1 airport
The best flight deal from Laredo, Texas to Chicago found on momondo in the last 72 hours is $204
The fastest flight from Laredo, Texas to Chicago takes 4h 57m
There are no direct flights from Laredo, Texas to Chicago. Popular non-direct route for this connection is Laredo Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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 57m, 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 $243Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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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