$536 Cheap Flights from Chicago (MDW) to Laredo (LRD)

View $536 flight on Sat, Sep 6, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Laredo, TX (LRD-Laredo Intl.)

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Cheap Flights from Chicago to Laredo (MDW-LRD)

Prices were available within the past 7 days and start at $536 for one-way flights and $1,072 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
LRD
Laredo
$1,072 Roundtrip, found 2 days ago
$1,072
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Laredo, returning Sat, Sep 27, priced at $1,072 found 2 days ago
Delta
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
LRD
Laredo
$1,084 Roundtrip, found 2 days ago
$1,084
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Laredo, returning Sat, Sep 27, priced at $1,084 found 2 days ago
Delta
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
LRD
Laredo
$1,096 Roundtrip, found 2 days ago
$1,096
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Laredo, returning Sat, Sep 27, priced at $1,096 found 2 days ago
Delta
Tue, Aug 26 - Tue, Sep 2
MDW
Chicago
LRD
Laredo
$1,121 Roundtrip, found 1 hour ago
$1,121
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Laredo, returning Tue, Sep 2, priced at $1,121 found 1 hour ago
Delta
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
LRD
Laredo
$1,134 Roundtrip, found 2 days ago
$1,134
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Laredo, returning Sat, Sep 27, priced at $1,134 found 2 days ago
Delta
Tue, Aug 26 - Tue, Sep 2
MDW
Chicago
LRD
Laredo
$1,140 Roundtrip, found 1 hour ago
$1,140
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Laredo, returning Tue, Sep 2, priced at $1,140 found 1 hour ago
Delta
Tue, Aug 26 - Tue, Sep 2
MDW
Chicago
LRD
Laredo
$1,141 Roundtrip, found 1 hour ago
$1,141
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Laredo, returning Tue, Sep 2, priced at $1,141 found 1 hour ago
Delta
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
LRD
Laredo
$1,146 Roundtrip, found 2 days ago
$1,146
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Laredo, returning Sat, Sep 27, priced at $1,146 found 2 days ago
Delta
Tue, Aug 26 - Tue, Sep 2
MDW
Chicago
LRD
Laredo
$1,160 Roundtrip, found 1 hour ago
$1,160
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Laredo, returning Tue, Sep 2, priced at $1,160 found 1 hour ago
Delta
Tue, Aug 26 - Tue, Sep 2
MDW
Chicago
LRD
Laredo
$1,162 Roundtrip, found 1 hour ago
$1,162
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Laredo, returning Tue, Sep 2, priced at $1,162 found 1 hour ago

Alternative airports near Laredo

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Laredo Intl. LRD. Cheapest and Closest option available. Average driving time to city center is 6 minutes. Flights from $1,362
LRD
Laredo Intl.
CheapestClosest
Average driving time to city center6 min
Flights from $1,362
Flights from Chicago (MDW) to Laredo (LRD)
Origin airport
Midway Intl.
Destination airport
Laredo Intl.
Roundtrip price
$1,071
Distance
1185 mi

Chicago to Laredo Flights

The cheapest times to fly from Chicago to Laredo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Laredo are during the month of September. You can find some of the cheapest flights from Chicago to Laredo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Laredo

Sunday is one of the best days to book for cheap flights from Chicago to Laredo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Laredo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Laredo in 2025. You can also book with separate airlines for your outbound and return journeys, from $536 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Laredo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Laredo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD) cost?
Lock in a cheap one-way flight from $536 or cheap return flight from $1,072 from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD)?
September is the most affordable month to fly from MDW to LRD. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from MDW to LRD. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD)?
You'll have to take a flight with a layover when traveling from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to LRD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary depending on various factors, such as the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD) route, travel before 3 PM. Flights after this time have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD) last-minute?
Last-minute fares from MDW to LRD are usually more expensive. To secure the best rates, start looking for flights well in advance. That said, if you can play around with your travel dates, you may score a cheap ticket right before your trip.
Is it cheaper to book a MDW to LRD flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to LRD flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one place will take the stress out of travel planning. Just pick your flights and choose from our wide range of hotels, then personalize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Laredo Intl. Airport (LRD)?
In most instances, you can modify or cancel your MDW to LRD flight. However, additional charges may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you need more details, go to our Customer Service portal.

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*Available to One Key members.