There are 7 ways to get from Chicago to Cabo Rojo 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 Aguadilla, drive
best- Fly from Chicago O'Hare International Airport (ORD) to Aguadilla (BQN)plane ORD - BQN
- Drive from Aguadilla (BQN) to Cabo Rojocar
10h$138–564Fly Chicago O'Hare International Airport to Eugenio María De Hostos Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Eugenio María De Hostos Airport (MAZ)plane ORD - MAZ
10h 3m$74–319Fly Chicago Midway International Airport to Aguadilla, drive
- Fly from Chicago Midway International Airport (MDW) to Aguadilla (BQN)plane MDW - BQN
- Drive from Aguadilla (BQN) to Cabo Rojocar
9h 28m$198–864Fly Chicago O'Hare International Airport to Ponce, drive
- Fly from Chicago O'Hare International Airport (ORD) to Ponce (PSE)plane ORD - PSE
- Drive from Ponce (PSE) to Cabo Rojocar
10h 56m$140–617Fly Chicago Midway International Airport to Ponce, drive
- Fly from Chicago Midway International Airport (MDW) to Ponce (PSE)plane MDW - PSE
- Drive from Ponce (PSE) to Cabo Rojocar
10h 16m$200–867Fly Chicago O'Hare International Airport to Luis Munoz Marin International Airport, shuttle, drive
- Fly from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU)plane ORD - SJU
- Take a shuttle bus from San Juan Airport to Hilton Ponce Golf & Casino Resort
- Drive from Hilton Ponce Golf & Casino Resort to Cabo Rojocar
10h 59m$334–622Fly Chicago Midway International Airport to Luis Munoz Marin International Airport, shuttle, drive
- Fly from Chicago Midway International Airport (MDW) to Luis Munoz Marin International Airport (SJU)plane MDW - SJU
- Take a shuttle bus from San Juan Airport to Hilton Ponce Golf & Casino Resort
- Drive from Hilton Ponce Golf & Casino Resort to Cabo Rojocar
10h 46m$394–982
Chicago O'Hare International Airport (ORD) to Aguadilla (BQN) flights
Questions & Answers
The cheapest way to get from Chicago to Cabo Rojo is to fly which costs $70 - $320 and takes 10h 3m.
The fastest way to get from Chicago to Cabo Rojo is to fly and drive which takes 9h 28m and costs $190 - $900.
The distance between Chicago and Cabo Rojo is 3347 km.
It takes approximately 10h to get from Chicago to Cabo Rojo, including transfers.
Cabo Rojo is 2h ahead of Chicago. It is currently 10:58 AM in Chicago and 12:58 PM in Cabo Rojo.
There are 164+ hotels available in Cabo Rojo.
What companies run services between Chicago, IL, USA and Cabo Rojo, Puerto Rico?
American Airlines, Cape Air, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Eugenio María De Hostos Airport (MAZ) twice daily.
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Aguadilla via New York JFK
- Ave. Duration
- 9h 59m
- When
- Every day
- Estimated price
- $140–600
Flights from Chicago O'Hare International Airport to Aguadilla via Orlando
- Ave. Duration
- 6h 33m
- When
- Every day
- Estimated price
- $130–550
Flights from Chicago O'Hare International Airport to Aguadilla via Fort Lauderdale
- Ave. Duration
- 6h 37m
- When
- Every day
- Estimated price
- $210–750
Flights from Chicago Midway International Airport to Aguadilla via Orlando
- Ave. Duration
- 6h 58m
- When
- Saturday
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Aguadilla via Fort Lauderdale
- Ave. Duration
- 8h 32m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Ponce via New York JFK
- Ave. Duration
- 8h 41m
- When
- Every day
- Estimated price
- $140–600
Flights from Chicago O'Hare International Airport to Ponce via Orlando
- Ave. Duration
- 7h 6m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $130–600
Flights from Chicago Midway International Airport to Ponce via Orlando
- Ave. Duration
- 6h 43m
- When
- Friday
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Ponce via Covington, Orlando
- Ave. Duration
- 10h 26m
- When
- Monday
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Ponce via Nashville, Orlando
- Ave. Duration
- 10h 31m
- When
- Thursday and Friday
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Eugenio María De Hostos Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 7h 57m
- When
- Every day
- Estimated price
- $70–310
Flights from Chicago O'Hare International Airport to Eugenio María De Hostos Airport via Christiansted, Luis Munoz Marin International Airport
- Ave. Duration
- 8h 36m
- When
- Saturday
- Estimated price
- $75–330
Flights from Chicago O'Hare International Airport to Eugenio María De Hostos Airport via Atlanta, Luis Munoz Marin International Airport
- Ave. Duration
- 11h 18m
- When
- Every day
- Estimated price
- $75–320
- Website
- southwest.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 50m
- When
- Monday to Friday
- Estimated price
- $110–490
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 6h 36m
- When
- Thursday to Sunday
- Estimated price
- $120–550
Flights from Chicago Midway International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 35m
- When
- Saturday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 6h 35m
- When
- Monday to Friday
- Estimated price
- $180–750
Flights from Chicago Midway International Airport to Luis Munoz Marin International Airport via Fort Lauderdale
- Ave. Duration
- 7h
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $180–800
- Website
- flyfrontier.com
Flights from Chicago O'Hare International Airport to Aguadilla via Orlando
- Ave. Duration
- 9h 7m
- When
- Monday, Friday, and Saturday
- Estimated price
- $130–550
Flights from Chicago Midway International Airport to Aguadilla via Orlando
- Ave. Duration
- 6h 47m
- When
- Monday, Thursday, and Friday
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Ponce via Orlando
- Ave. Duration
- 11h 19m
- When
- Friday
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 6h 53m
- When
- Monday, Friday, and Saturday
- Estimated price
- $120–550
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Punta Cana
- Ave. Duration
- 7h 49m
- When
- Friday
- Estimated price
- $110–500
Flights from Chicago Midway International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 7h 45m
- When
- Friday
- Estimated price
- $180–750
- Website
- united.com
Flights from Chicago O'Hare International Airport to Aguadilla via Newark
- Ave. Duration
- 7h 22m
- When
- Monday, Tuesday, Thursday, Friday, and Saturday
- Estimated price
- $130–600
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $110–490
- Website
- spirit.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $110–390
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Fort Lauderdale
- Ave. Duration
- 8h 16m
- When
- Every day
- Estimated price
- $110–390
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport via Orlando
- Ave. Duration
- 8h 25m
- When
- Every day
- Estimated price
- $110–390
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Luis Munoz Marin International Airport
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $110–490
- Website
- capeair.com
Flights from Chicago O'Hare International Airport to Eugenio María De Hostos Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 7h 57m
- When
- Every day
- Estimated price
- $70–310
Flights from Chicago O'Hare International Airport to Eugenio María De Hostos Airport via Atlanta, Luis Munoz Marin International Airport
- Ave. Duration
- 11h 18m
- When
- Every day
- Estimated price
- $75–320
Shuttle from San Juan Airport to Hilton Ponce Golf & Casino Resort
- Ave. Duration
- 2h 10m
- Frequency
- On demand
- Estimated price
- $215
- Website
- https://www.puertoricoshuttle.com/
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