Cheap Flights from Laredo to Chicago
Cheap Flights from Laredo to Chicago
Looking for cheap flights from Laredo to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Laredo to Chicago vary by season, cabin, and date, but available award flights can start around 8,500–18,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Laredo to Chicago for specific travel dates.
2026-11-29
LRD - ORD
Economy | 2 Stops
From 8,500 Pts + $11.2
2026-11-30
LRD - ORD
Economy | 2 Stops
From 8,500 Pts + $11.2
2026-11-30
LRD - ORD
Economy | 1 Stop | 9+ left
From 12,500 Pts + $31.2
2026-11-30
LRD - ORD
Economy | 1 Stop
From 13,800 Pts + $11.2
2026-11-29
LRD - ORD
First | 2 Stops
From 18,500 Pts + $11.2
2026-11-30
LRD - ORD
First | 2 Stops
From 18,500 Pts + $11.2
Laredo to Chicago flight facts
Distance
1,184 mi
1,906 km in a straight line
Estimated flight time
about 2h 45m
In the air, for the straight-line distance
Time difference
Same time zone
Chicago is in the same time zone as Laredo.
Airports in Laredo
LRD · Laredo Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Monterrey - Chicago · Monterrey is 128 mi from Laredo
Flights Harlingen - Chicago · Harlingen is 144 mi from Laredo
Flights San Antonio - Chicago · San Antonio is 150 mi from Laredo
Premium cabin flights from Laredo to Chicago
Premium cabin
2026-11-29
LRD - ORD
First | 1 Stop | 7 left
From 25,000 Pts + $31.2
Premium cabin
2026-11-29
LRD - ORD
Business | 1 Stop
From 29,000 Pts + $11.2
Premium cabin
2026-11-29
LRD - ORD
First | 2 Stops
From 18,500 Pts + $11.2
Premium cabin
2026-11-30
LRD - ORD
First | 2 Stops
From 18,500 Pts + $11.2
Premium cabin
2026-11-30
LRD - ORD
First | 1 Stop | 9+ left
From 25,000 Pts + $31.2
Premium cabin
2026-11-30
LRD - ORD
Business | 1 Stop
From 29,000 Pts + $11.2
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Laredo to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Laredo to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Laredo to Chicago.
Laredo and Chicago are about 1,184 miles (1,906 km) apart in a straight line.
Flying the 1,184-mile straight-line distance takes about 2h 45m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is in the same time zone as Laredo.
Departures from Laredo: Laredo Intl (LRD). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
Our mission is to provide
the simplest and best
points travel planning
experience. Yeah!
Our mission is to provide the simplest and best
points travel planning experience. Yeah!
