There are 5 ways to get from Puerto Rico to Chicago by plane
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Eugenio María De Hostos Airport to Chicago O'Hare International Airport
best- Fly from Eugenio María De Hostos Airport (MAZ) to Chicago O'Hare International Airport (ORD)plane MAZ - ORD
8h 46m$93–406Fly Ponce to Chicago O'Hare International Airport
- Fly from Ponce (PSE) to Chicago O'Hare International Airport (ORD)plane PSE - ORD
8h 30m$123–556Fly Aguadilla to Chicago Midway International Airport
- Fly from Aguadilla (BQN) to Chicago Midway International Airport (MDW)plane BQN - MDW
8h 11m$176–761Fly Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Fly from Luis Munoz Marin International Airport (SJU) to Chicago O'Hare International Airport (ORD)plane SJU - ORD
8h 12m$184–457Fly Luis Munoz Marin International Airport to Chicago Midway International Airport
- Fly from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW)plane SJU - MDW
8h 21m$194–667
Eugenio María De Hostos Airport (MAZ) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Puerto Rico to Chicago is to fly which costs $90 - $410 and takes 8h 46m.
The fastest way to get from Puerto Rico to Chicago is to fly which takes 8h 11m and costs $170 - $800.
The distance between Puerto Rico and Chicago is 2078 miles.
It takes approximately 8h 46m to get from Puerto Rico to Chicago, including transfers.
Chicago is 2h behind Puerto Rico. It is currently 12:03 PM in Puerto Rico and 10:03 AM in Chicago.
There are 996+ hotels available in Chicago.
What companies run services between Puerto Rico and Chicago, IL, USA?
Cape Air, United Airlines, and three other airlines fly from Eugenio María De Hostos Airport (MAZ) to Chicago O'Hare International Airport (ORD) 5 times a day.
- Website
- delta.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport, Atlanta
- Ave. Duration
- 9h 54m
- When
- Every day
- Estimated price
- $95–400
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 7h 36m
- When
- Every day
- Estimated price
- $95–410
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 8h 58m
- When
- Every day
- Estimated price
- $130–600
- Website
- southwest.com
Flights from Ponce to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 7h 40m
- When
- Every day
- Estimated price
- $120–550
Flights from Aguadilla to Chicago Midway International Airport via Orlando
- Ave. Duration
- 7h 49m
- When
- Every day
- Estimated price
- $170–750
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 5m
- When
- Monday, Thursday, and Friday
- Estimated price
- $90–400
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport
- Ave. Duration
- 5h 20m
- When
- Saturday
- Estimated price
- $130–600
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Tampa
- Ave. Duration
- 7h 40m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $140–600
- Website
- united.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 9h 1m
- When
- Every day
- Estimated price
- $90–400
Flights from Ponce to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 8h 36m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $120–550
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 25m
- When
- Every day
- Estimated price
- $90–400
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 8h 2m
- When
- Every day
- Estimated price
- $95–410
- Website
- flyfrontier.com
Flights from Aguadilla to Chicago Midway International Airport via Orlando
- Ave. Duration
- 7h 21m
- When
- Monday, Thursday, and Friday
- Estimated price
- $170–750
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 9h
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $95–410
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 7h 38m
- When
- Every day
- Estimated price
- $130–600
- Website
- aa.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 7h 51m
- When
- Every day
- Estimated price
- $90–400
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 33m
- When
- Every day
- Estimated price
- $90–400
- Website
- spirit.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 8h 30m
- When
- Every day
- Estimated price
- $150–550
Flights from Ponce to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 7h 38m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $120–550
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 15m
- When
- Every day
- Estimated price
- $120–390
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