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Cheap flights from Laredo, Texas to Chicago from $245

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 10/14. 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
3:53 pm - 11:12 pm
LRD
-
ORD
7h 19m
1 stop
American Airlines Logo
12:04 pm - 7:37 pm
ORD
-
LRD
7h 33m
1 stop
$245American Airlines
Wed, Oct 14 - Sat, Oct 17
American Airlines Logo
6:32 pm - 11:32 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$282American Airlines
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
6:44 pm - 12:39 am
LRD
-
ORD
5h 55m
1 stop
American Airlines Logo
5:00 am - 10:09 am
ORD
-
LRD
5h 09m
1 stop
$297American Airlines
Sat, Jun 6 - Sat, Jun 13
American Airlines Logo
6:32 pm - 11:32 pm
LRD
-
ORD
5h 00m
1 stop
American Airlines Logo
8:19 am - 3:04 pm
ORD
-
LRD
6h 45m
1 stop
$344American Airlines
Fri, Jun 12 - Thu, Jun 18
American Airlines Logo
3:34 pm - 11:39 pm
LRD
-
ORD
8h 05m
1 stop
American Airlines Logo
5:00 am - 10:01 am
ORD
-
LRD
5h 01m
1 stop
$350American Airlines
Tue, Jul 7 - Tue, Jul 28
American Airlines Logo
6:44 pm - 12:42 am
LRD
-
ORD
5h 58m
1 stop
American Airlines Logo
11:50 am - 6:02 pm
ORD
-
LRD
6h 12m
1 stop
$363American Airlines
Sat, May 30 - Tue, Jun 2
American Airlines Logo
6:44 pm - 12:42 am
LRD
-
ORD
5h 58m
1 stop
American Airlines Logo
1:29 pm - 7:37 pm
ORD
-
LRD
6h 08m
1 stop
$366American Airlines
Fri, May 29 - Tue, Jun 2
American Airlines Logo
6:53 pm - 12:50 am
LRD
-
ORD
5h 57m
1 stop
American Airlines Logo
11:59 am - 7:45 pm
ORD
-
LRD
7h 46m
1 stop
$369American Airlines
Fri, Jul 24 - Fri, Jul 31
American Airlines Logo
3:53 pm - 11:58 pm
LRD
-
ORD
8h 05m
1 stop
American Airlines Logo
5:00 am - 10:13 am
ORD
-
LRD
5h 13m
1 stop
$372American Airlines
Wed, Aug 5 - Sun, Aug 9
American Airlines Logo
6:19 pm - 12:06 am
LRD
-
ORD
5h 47m
1 stop
American Airlines Logo
1:39 pm - 7:37 pm
ORD
-
LRD
5h 58m
1 stop
$374American Airlines
Fri, Sep 18 - Tue, Sep 22

United Airlines flights from Laredo, Texas to Chicago

Our best United Airlines deals on Laredo, Texas to Chicago flight tickets
United Airlines
Jun 30
LRD2:06 pmLaredo
5h 59m
1 stop
ORD8:05 pmChicago O'Hare Intl
Jul 6
ORD5:45 pmChicago O'Hare Intl
5h 14m
1 stop
LRD10:59 pmLaredo
$409
United Airlines
Jun 5
LRD2:06 pmLaredo
7h 45m
1 stop
ORD9:51 pmChicago O'Hare Intl
Jun 8
ORD5:45 pmChicago O'Hare Intl
5h 14m
1 stop
LRD10:59 pmLaredo
$486
United Airlines
Oct 22
LRD2:05 pmLaredo
16h 33m
2 stops
ORD6:38 amChicago O'Hare Intl
Oct 25
ORD6:00 amChicago O'Hare Intl
5h 12m
1 stop
LRD11:12 amLaredo
$508

American Airlines flights from Laredo, Texas to Chicago

Our best American Airlines deals on Laredo, Texas to Chicago flight tickets
American Airlines
Oct 14
LRD3:53 pmLaredo
7h 19m
1 stop
ORD11:12 pmChicago O'Hare Intl
Oct 17
ORD12:04 pmChicago O'Hare Intl
7h 33m
1 stop
LRD7:37 pmLaredo
$245
American Airlines
Jun 10
LRD6:32 pmLaredo
5h 00m
1 stop
ORD11:32 pmChicago O'Hare Intl
Jun 17
ORD5:00 amChicago O'Hare Intl
5h 09m
1 stop
LRD10:09 amLaredo
$282
American Airlines
Jun 6
LRD6:44 pmLaredo
5h 55m
1 stop
ORD12:39 amChicago O'Hare Intl
Jun 13
ORD5:00 amChicago O'Hare Intl
5h 09m
1 stop
LRD10:09 amLaredo
$297

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 May 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

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 10/14

3:53 pm-11:12 pm

1 stop7h 19m

Chicago O'Hare Intl

Sat 10/17

12:04 pm-7:37 pm

1 stop7h 33m

$245
Quickest round-trip

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 6/10

6:32 pm-11:32 pm

1 stop5h 00m

Chicago O'Hare Intl

Wed 6/17

5:00 am-10:09 am

1 stop5h 09m

$282

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 6/6

6:44 pm-12:39 am

1 stop5h 55m

Chicago O'Hare Intl

Sat 6/13

5:00 am-10:09 am

1 stop5h 09m

$297

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 6/12

6:32 pm-11:32 pm

1 stop5h 00m

Chicago O'Hare Intl

Thu 6/18

8:19 am-3:04 pm

1 stop6h 45m

$344

LaredoChicago

LRD - ORD

LRDORD

Laredo

Tue 7/7

3:34 pm-11:39 pm

1 stop8h 05m

Chicago O'Hare Intl

Tue 7/28

5:00 am-10:01 am

1 stop5h 01m

$350

LaredoChicago

LRD - ORD

LRDORD

Laredo

Sat 5/30

6:44 pm-12:42 am

1 stop5h 58m

Chicago O'Hare Intl

Tue 6/2

11:50 am-6:02 pm

1 stop6h 12m

$363

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 5/29

6:44 pm-12:42 am

1 stop5h 58m

Chicago O'Hare Intl

Tue 6/2

1:29 pm-7:37 pm

1 stop6h 08m

$366

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 7/24

6:53 pm-12:50 am

1 stop5h 57m

Chicago O'Hare Intl

Fri 7/31

11:59 am-7:45 pm

1 stop7h 46m

$369

LaredoChicago

LRD - ORD

LRDORD

Laredo

Wed 8/5

3:53 pm-11:58 pm

1 stop8h 05m

Chicago O'Hare Intl

Sun 8/9

5:00 am-10:13 am

1 stop5h 13m

$372

LaredoChicago

LRD - ORD

LRDORD

Laredo

Fri 9/18

6:19 pm-12:06 am

1 stop5h 47m

Chicago O'Hare Intl

Tue 9/22

1:39 pm-7:37 pm

1 stop5h 58m

$374

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 $204. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Laredo, Texas to Chicago during January average around $204.

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 52m

Direct flights

None
The fastest flight from Laredo, Texas to Chicago takes 5h 52m
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 52m, 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
9,737 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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