There are 4 ways to get from Chicago to Old San Juan by plane, car, or shuttle
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago O'Hare International Airport to Luis Munoz Marin International Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU)plane ORD - SJU
8h 25m$238–685Fly Chicago O'Hare International Airport to Aguadilla, drive
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Aguadilla (BQN)plane ORD - BQN
- Drive from Aguadilla (BQN) to Old San Juancar
11h 24m$206–627Fly Chicago Midway International Airport to Luis Munoz Marin International Airport
- Fly from Chicago Midway International Airport (MDW) to Luis Munoz Marin International Airport (SJU)plane MDW - SJU
8h 14m$258–885Fly Chicago O'Hare International Airport to Ponce, shuttle
- Fly from Chicago O'Hare International Airport (ORD) to Ponce (PSE)plane ORD - PSE
- Take a shuttle bus from Hilton Ponce Golf & Casino Resort to San Juan Airport
14h 51m$398–957
Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) flights
Questions & Answers
The cheapest way to get from Chicago to Old San Juan is to fly and drive which costs $200 - $650 and takes 11h 24m.
The fastest way to get from Chicago to Old San Juan is to fly which takes 8h 14m and costs $250 - $900.
The distance between Chicago and Old San Juan is 3380 km.
It takes approximately 8h 25m to get from Chicago to Old San Juan, including transfers.
Old San Juan is 1h ahead of Chicago. It is currently 11:59 AM in Chicago and 12:59 PM in Old San Juan.
There are 1240+ hotels available in Old San Juan.
What companies run services between Chicago, IL, USA and Old San Juan, Puerto Rico?
American Airlines, United Airlines, and four other airlines fly from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) every 2 hours.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 50m
- When
- Saturday
- Estimated price
- $200–800
Flights from Chicago Midway International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 7h 22m
- When
- Sunday, Monday, Thursday, Friday, Tuesday, and Wednesday
- Estimated price
- $210–850
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Fort Lauderdale
- Ave. Duration
- 7h 32m
- When
- Every day
- Estimated price
- $170–700
Flights from Chicago O'Hare International Airport to Aguadilla via New York JFK
- Ave. Duration
- 7h 57m
- When
- Every day
- Estimated price
- $180–700
Flights from Chicago O'Hare International Airport to Aguadilla via Fort Lauderdale
- Ave. Duration
- 7h 55m
- When
- Every day
- Estimated price
- $170–700
Flights from Chicago O'Hare International Airport to Ponce via Fort Lauderdale
- Ave. Duration
- 12h 11m
- When
- Every day
- Estimated price
- $170–700
Flights from Chicago O'Hare International Airport to Ponce via Orlando
- Ave. Duration
- 11h 11m
- When
- Every day
- Estimated price
- $170–700
- Website
- flyfrontier.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Fort Lauderdale
- Ave. Duration
- 7h 3m
- When
- Every day
- Estimated price
- $180–600
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 7h 58m
- When
- Every day
- Estimated price
- $180–600
Flights from Chicago O'Hare International Airport to Aguadilla via Orlando
- Ave. Duration
- 7h 26m
- When
- Every day
- Estimated price
- $190–600
Flights from Chicago O'Hare International Airport to Ponce via Orlando
- Ave. Duration
- 15h 28m
- When
- Every day
- Estimated price
- $190–650
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 55m
- When
- Every day
- Estimated price
- $160–650
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Miami
- Ave. Duration
- 7h 45m
- When
- Every day
- Estimated price
- $170–700
- Website
- united.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 49m
- When
- Every day
- Estimated price
- $160–650
Flights from Chicago O'Hare International Airport to Aguadilla via Newark
- Ave. Duration
- 7h 38m
- When
- Every day
- Estimated price
- $180–700
- Website
- arajet.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Punta Cana
- Ave. Duration
- 8h 35m
- When
- Friday
- Estimated price
- $230–1,000
- Website
- worldticket.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Punta Cana
- Ave. Duration
- 8h 35m
- When
- Friday
- Estimated price
- $230–1,000
Shuttle from Hilton Ponce Golf & Casino Resort to San Juan Airport
- Ave. Duration
- 2h 10m
- Frequency
- On demand
- Estimated price
- $150–220
- Website
- https://www.puertoricoshuttle.com/
Want to know more about travelling around Puerto Rico
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