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 5m$98–436Fly Aguadilla to Chicago O'Hare International Airport
- Fly from Aguadilla (BQN) to Chicago O'Hare International Airport (ORD)plane BQN - ORD
8h 30m$116–561Fly Ponce to Chicago Midway International Airport
- Fly from Ponce (PSE) to Chicago Midway International Airport (MDW)plane PSE - MDW
8h 28m$193–856Fly 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 16m$177–460Fly 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 11m$207–780
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 $95 - $440 and takes 8h 5m.
The fastest way to get from Puerto Rico to Chicago is to fly which takes 8h 5m and costs $95 - $440.
The distance between Puerto Rico and Chicago is 2078 miles.
It takes approximately 8h 5m to get from Puerto Rico to Chicago, including transfers.
Chicago is 1h behind Puerto Rico. It is currently 4:58 PM in Puerto Rico and 3:58 PM in Chicago.
There are 900+ 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) 3 times a day.
- Website
- southwest.com
Flights from Ponce to Chicago Midway International Airport via Orlando
- Ave. Duration
- 8h 55m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $190–850
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport
- Ave. Duration
- 5h 10m
- When
- Saturday
- Estimated price
- $150–700
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Tampa
- Ave. Duration
- 7h 56m
- When
- Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $160–750
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 9h 30m
- When
- Saturday
- Estimated price
- $160–750
- Website
- flyfrontier.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 7h 10m
- When
- Wednesday, Thursday, and Sunday
- Estimated price
- $95–430
Flights from Aguadilla to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 11h 37m
- When
- Monday, Friday, and Sunday
- Estimated price
- $110–550
Flights from Ponce to Chicago Midway International Airport via Orlando
- Ave. Duration
- 8h 56m
- When
- Friday and Sunday
- Estimated price
- $190–850
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 22m
- When
- Wednesday, Thursday, and Sunday
- Estimated price
- $95–420
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 8h 36m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $100–440
- Website
- united.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 7h 56m
- When
- Every day
- Estimated price
- $95–430
Flights from Aguadilla to Chicago O'Hare International Airport via Newark
- Ave. Duration
- 8h 28m
- When
- Every day
- Estimated price
- $120–550
Flights from Aguadilla to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 7h 10m
- When
- Every day
- Estimated price
- $110–550
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $95–420
- Website
- delta.com
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 7h 37m
- When
- Every day
- Estimated price
- $100–440
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 8h
- When
- Every day
- Estimated price
- $100–440
- 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 30m
- When
- Every day
- Estimated price
- $95–430
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 39m
- When
- Every day
- Estimated price
- $95–420
- 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 33m
- When
- Every day
- Estimated price
- $160–550
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 9m
- When
- Every day
- Estimated price
- $120–380
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