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Cheap flights from Laredo to Chicago from $309

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 to Chicago departing on 3/3. 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
3:35 pm - 11:04 pm
LRD
-
ORD
7h 29m
1 stop
United Airlines Logo
2:10 pm - 8:07 pm
ORD
-
LRD
5h 57m
1 stop
$309United Airlines
Tue, Mar 3 - Sat, Mar 7
Multiple Airlines Logo
10:25 pm - 10:39 pm
LRD
-
ORD
24h 14m
2 stops
Multiple Airlines Logo
9:18 pm - 8:47 pm
ORD
-
LRD
23h 29m
1 stop
$369Multiple Airlines
Mon, Apr 6 - Sun, Apr 19
United Airlines Logo
3:15 pm - 11:15 pm
LRD
-
ORD
8h 00m
1 stop
United Airlines Logo
4:03 pm - 9:22 pm
ORD
-
LRD
5h 19m
1 stop
$371United Airlines
Tue, Mar 31 - Sat, Apr 11
American Airlines Logo
6:28 pm - 11:36 pm
LRD
-
ORD
5h 08m
1 stop
American Airlines Logo
6:49 pm - 11:59 pm
ORD
-
LRD
5h 10m
1 stop
$373American Airlines
Wed, Mar 18 - Wed, Mar 25
American Airlines Logo
3:33 pm - 11:37 pm
LRD
-
ORD
8h 04m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$375American Airlines
Mon, May 25 - Sat, May 30
United Airlines Logo
3:15 pm - 11:15 pm
LRD
-
ORD
8h 00m
1 stop
United Airlines Logo
5:48 am - 11:28 am
ORD
-
LRD
5h 40m
1 stop
$381United Airlines
Tue, Mar 31 - Thu, Apr 9
American Airlines Logo
2:25 pm - 10:00 pm
LRD
-
ORD
7h 35m
1 stop
American Airlines Logo
2:58 pm - 10:59 pm
ORD
-
LRD
8h 01m
1 stop
$396American Airlines
Sat, Feb 28 - Tue, Mar 3
Multiple Airlines Logo
10:25 pm - 10:39 pm
LRD
-
ORD
24h 14m
2 stops
Multiple Airlines Logo
9:18 pm - 8:47 pm
ORD
-
LRD
23h 29m
1 stop
$400Multiple Airlines
Mon, Apr 6 - Thu, Apr 16
United Airlines Logo
12:13 pm - 7:44 am
LRD
-
ORD
19h 31m
1 stop
United Airlines Logo
7:30 am - 2:30 pm
ORD
-
LRD
7h 00m
1 stop
$414United Airlines
Fri, Apr 3 - Sat, Apr 11
United Airlines Logo
12:13 pm - 7:44 am
LRD
-
ORD
19h 31m
1 stop
United Airlines Logo
5:48 am - 11:28 am
ORD
-
LRD
5h 40m
1 stop
$424United Airlines
Fri, Apr 3 - Mon, Apr 20

United Airlines flights from Laredo to Chicago

Our best United Airlines deals on Laredo to Chicago flight tickets
United Airlines
Mar 3
LRD3:35 pmLaredo
7h 29m
1 stop
ORD11:04 pmChicago O'Hare Intl
Mar 7
ORD2:10 pmChicago O'Hare Intl
5h 57m
1 stop
LRD8:07 pmLaredo
$309
United Airlines
Mar 31
LRD3:15 pmLaredo
8h 00m
1 stop
ORD11:15 pmChicago O'Hare Intl
Apr 11
ORD4:03 pmChicago O'Hare Intl
5h 19m
1 stop
LRD9:22 pmLaredo
$371
United Airlines
Mar 31
LRD3:15 pmLaredo
8h 00m
1 stop
ORD11:15 pmChicago O'Hare Intl
Apr 9
ORD5:48 amChicago O'Hare Intl
5h 40m
1 stop
LRD11:28 amLaredo
$381

American Airlines flights from Laredo to Chicago

Our best American Airlines deals on Laredo to Chicago flight tickets
American Airlines
Feb 26
LRD5:00 amLaredo
6h 03m
1 stop
ORD11:03 amChicago O'Hare Intl
Feb 28
ORD4:49 pmChicago O'Hare Intl
6h 10m
1 stop
LRD10:59 pmLaredo
$361
American Airlines
Mar 18
LRD6:28 pmLaredo
5h 08m
1 stop
ORD11:36 pmChicago O'Hare Intl
Mar 25
ORD6:49 pmChicago O'Hare Intl
5h 10m
1 stop
LRD11:59 pmLaredo
$373
American Airlines
May 25
LRD3:33 pmLaredo
8h 04m
1 stop
ORD11:37 pmChicago O'Hare Intl
May 30
ORD5:00 amChicago O'Hare Intl
5h 09m
1 stop
LRD10:09 amLaredo
$375

momondo Fare Finder

 
Customize your flight search to find flights from Laredo 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 February 17, 2026.
Use the filters below to find and compare flights from Laredo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 3/3

3:35 pm-11:04 pm

1 stop7h 29m

Chicago O'Hare Intl

Sat 3/7

2:10 pm-8:07 pm

1 stop5h 57m

$309

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 4/6

10:25 pm-10:39 pm

2 stops24h 14m

Chicago O'Hare Intl

Sun 4/19

9:18 pm-8:47 pm

1 stop23h 29m

$369

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 3/31

3:15 pm-11:15 pm

1 stop8h 00m

Chicago O'Hare Intl

Sat 4/11

4:03 pm-9:22 pm

1 stop5h 19m

$371

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 3/18

6:28 pm-11:36 pm

1 stop5h 08m

Chicago O'Hare Intl

Wed 3/25

6:49 pm-11:59 pm

1 stop5h 10m

$373

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 5/25

3:33 pm-11:37 pm

1 stop8h 04m

Chicago O'Hare Intl

Sat 5/30

5:00 am-10:09 am

1 stop5h 09m

$375

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 3/31

3:15 pm-11:15 pm

1 stop8h 00m

Chicago O'Hare Intl

Thu 4/9

5:48 am-11:28 am

1 stop5h 40m

$381

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 2/28

2:25 pm-10:00 pm

1 stop7h 35m

Chicago O'Hare Intl

Tue 3/3

2:58 pm-10:59 pm

1 stop8h 01m

$396

LaredoChicago

LRD - ORD

LRDORD

Laredo

Mon 4/6

10:25 pm-10:39 pm

2 stops24h 14m

Chicago O'Hare Intl

Thu 4/16

9:18 pm-8:47 pm

1 stop23h 29m

$400

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 4/3

12:13 pm-7:44 am

1 stop19h 31m

Chicago O'Hare Intl

Sat 4/11

7:30 am-2:30 pm

1 stop7h 00m

$414

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 4/3

12:13 pm-7:44 am

1 stop19h 31m

Chicago O'Hare Intl

Mon 4/20

5:48 am-11:28 am

1 stop5h 40m

$424

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 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, 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 to Chicago during May average around $331.

How have Laredo to Chicago flight prices changed over time?

When to book flights from Laredo to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Laredo to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Laredo to Chicago (LRD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Laredo to Chicago

Fastest flight time

7h 29m

Direct flights

None
The fastest flight from Laredo to Chicago takes 7h 29m
There are no direct flights from Laredo to Chicago. There are no popular flight routes from Laredo 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 7h 29m, 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 to Chicago?

Best airlines flying from Laredo to Chicago

Compare and see reviews for airlines that fly from Laredo to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $204Free CancellationRating
7.2
11,294 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
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