Cheap Flights from Laredo to Chicago from $569

Compare Laredo to Chicago flight deals

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Flight deals from Laredo to Chicago

Looking for a cheap last-minute deal or the best return flight from Laredo Airport to Chicago? If you want to travel next month, return fares start from $618. Find the lowest prices on one-way and return tickets right here.

Chicago.$569 per passenger.Departing Tue, 15 Sep, returning Tue, 22 Sep.Return flight with United.Outbound indirect flight with United, departs from Laredo on Tue, 15 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Tue, 22 Sep, arriving in Laredo.Price includes taxes and charges.From $569, select.

Chicago.$616 per passenger.Departing Tue, 27 Oct, returning Sun, 1 Nov.Return flight with United.Outbound indirect flight with United, departs from Laredo on Tue, 27 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sun, 1 Nov, arriving in Laredo.Price includes taxes and charges.From $616, select.

Chicago.$618 per passenger.Departing Sat, 11 Jul, returning Wed, 15 Jul.Return flight with United.Outbound indirect flight with United, departs from Laredo on Sat, 11 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 15 Jul, arriving in Laredo.Price includes taxes and charges.From $618, select.

Chicago.$622 per passenger.Departing Sat, 13 Jun, returning Tue, 16 Jun.Return flight with United.Outbound indirect flight with United, departs from Laredo on Sat, 13 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Tue, 16 Jun, arriving in Laredo.Price includes taxes and charges.From $622, select.

Chicago.$666 per passenger.Departing Fri, 16 Oct, returning Tue, 20 Oct.Return flight with United.Outbound indirect flight with United, departs from Laredo on Fri, 16 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Tue, 20 Oct, arriving in Laredo.Price includes taxes and charges.From $666, select.

Chicago.$737 per passenger.Departing Tue, 30 Jun, returning Wed, 8 Jul.Return flight with United.Outbound indirect flight with United, departs from Laredo on Tue, 30 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 8 Jul, arriving in Laredo.Price includes taxes and charges.From $737, select.

Chicago.$827 per passenger.Departing Fri, 13 Nov, returning Mon, 16 Nov.Return flight with United.Outbound indirect flight with United, departs from Laredo on Fri, 13 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Mon, 16 Nov, arriving in Laredo.Price includes taxes and charges.From $827, select.

Chicago.$874 per passenger.Departing Fri, 7 Aug, returning Tue, 11 Aug.Return flight with United.Outbound indirect flight with United, departs from Laredo on Fri, 7 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Tue, 11 Aug, arriving in Laredo.Price includes taxes and charges.From $874, select.

Chicago.$886 per passenger.Departing Fri, 9 Apr, returning Sun, 11 Apr.Return flight with United.Outbound indirect flight with United, departs from Laredo on Fri, 9 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sun, 11 Apr, arriving in Laredo.Price includes taxes and charges.From $886, select.

Chicago.$1,051 per passenger.Departing Fri, 19 Feb, returning Mon, 22 Feb.Return flight with United.Outbound indirect flight with United, departs from Laredo on Fri, 19 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Mon, 22 Feb, arriving in Laredo.Price includes taxes and charges.From $1,051, select.

Find the cheapest month to fly from Laredo to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Laredo to Chicago flights are currently cheapest in September.

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Alternative Laredo to Chicago routes

Looking for the cheapest, fastest or easiest route from Laredo to Chicago? You could fly into the following airports instead.

Laredo to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$569
Cheapest month to fly	September

Finding cheap flights from Laredo to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Laredo to Chicago?

The best price we found for a return flight from Laredo to Chicago is $569. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Laredo to Chicago?

Currently, there are no airlines that fly direct from Laredo to Chicago. But we found flights with one or more stops from $569.

How many flights are there a week from Laredo to Chicago?

As of June 2026, there are no flights flying from Laredo to Chicago.

When is the cheapest time to fly from Laredo to Chicago?

The cheapest month to fly from Laredo to Chicago is usually September.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Laredo Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $569.

Which upcoming date is cheapest to fly from Laredo Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Laredo Airport to Chicago on Tuesday, 15 September 2026.

Can I get a direct flight from Laredo Airport to Chicago?

No airlines currently offer direct flights between Laredo Airport and Chicago. Most routes have one or more stops.

How can I get the best flight deal from Laredo Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Laredo Airport to Chicago with?

Currently, United offers the cheapest flight tickets to Chicago.

Travelling from Laredo International Airport (LRD) to Chicago: what you need to know

Chicago's timezone is UTC-6, which is the same as Laredo (the location of Laredo International Airport).
Leave plenty of time to get on your LRD to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.
Travelling during a peak time such as May? Major public holidays and other high seasons can mean longer queues and delays at check-in and security. Be extra cautious and arrive up to four hours before an international flight and two hours before a domestic departure.
Travelling from central Laredo to LRD takes around 45 minutes on public transport. If you drive, ride-share or get a taxi, you'll cover the 6 kilometres in 15 minutes or so, depending on traffic conditions.
Planning to catch an early flight from Laredo International Airport to Chicago? Avoid the hassle of rushing to the terminal (and sneak in some extra precious sleep) by choosing one of these stays close to LRD:
80% of flights leaving Laredo International Airport reach their destination according to schedule. With its reliable on-time performance, you're unlikely to be delayed when setting off from LRD.
You'll find LRD at 5210 Bob Bullock Loop.

How to find the cheapest flights from Laredo International Airport (LRD) to Chicago

$596 is the cheapest price we've seen for a one-way Laredo International Airport to Chicago flight. A round-trip plane ticket right now is $569. Depending on how early you book and the availability, these fares may change.
To find cheap flights from LRD to Chicago, book in advance. Airlines generally offer their most competitively priced fares when tickets first go on sale.
If you're willing to be flexible with your trip dates, use the 'Whole month' search tool. It'll find the cheapest price across every month when looking for a Laredo International Airport to Chicago ticket.
Stay on top of deals for cheap flights from LRD to Chicago by setting up a Price Alert. We'll send you an email or push notification on the app when fares go down.
Pick your ideal departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from Laredo International Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It'll take you around 30 minutes to get to the centre driving.
Travelling on public transport will take you around 45 minutes.
Consider staying in a hotel near ORD if you have a late flight from Laredo International Airport to Chicago. Choose one of these accommodation options and make your first night all about catching up on rest:
Booking your ride from Chicago O'Hare International Airport about four weeks before your flight from LRD to Chicago can help you lock in the lowest rate.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

The centre of Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Laredo International Airport to Chicago has touched down and you've navigated your way to arrivals, expect a drive of around 25 minutes.
If you choose to travel on public transport, the ride to the centre takes 30 minutes or so.
You'll find some comfortable places to rest your head close to MDW. Unwind and get cosy after your LRD to Chicago flight at one of these well-located options:
Score the best price by booking your ride from MDW four weeks ahead of time. You'll also have access to a greater range of vehicles.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Hop off your flight from Laredo International Airport to Chicago and head for your hotel or start exploring right away. The centre of Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to reach driving.
The journey takes roughly 2 hours using public transport.
Enjoy an unhurried start to your break by staying at a hotel near RFD after your LRD to Chicago flight. Recover from your travel day or simply give yourself time to find your footing in a new city at:
Booking a couple of weeks ahead of your flight from Laredo International Airport to Chicago is always smart. In addition to better deals, you'll get a better selection of vehicle makes and models at RFD.
Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Laredo International Airport to Chicago, while July is the most popular. Find the ideal time to go to Chicago based on whether you like a laid-back vibe or a more bustling atmosphere.
When booking your Laredo International Airport to Chicago plane ticket, think about the kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
January sees average temperatures of between -12ºC and 3ºC. Look for a cheap ticket from LRD to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

Once you've booked your flight from Laredo International Airport to Chicago, find a hotel that offers both comfort and a great location. Make one of these options your base for exploring Chicago:
All great holidays should include some sightseeing. Art Institute of Chicago, Millennium Park and Willis Tower are must-do's during your Chicago adventure.

Explore more of the United States

You've seen Chicago, now it's time to explore more of the United States. Journey about 451 kilometres southeast to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, your itinerary will be busy.
Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.