There are 6 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 Ponce to Chicago O'Hare International Airport
best- Fly from Ponce (PSE) to Chicago O'Hare International Airport (ORD)plane PSE - ORD
8h 40m$123–556Fly Eugenio María De Hostos Airport to Chicago O'Hare International Airport
cheapest- Fly from Eugenio María De Hostos Airport (MAZ) to Chicago O'Hare International Airport (ORD)plane MAZ - ORD
8h 40m$93–376Fly Ponce to Chicago Midway International Airport
- Fly from Ponce (PSE) to Chicago Midway International Airport (MDW)plane PSE - MDW
7h 45m$163–706Fly Aguadilla to Chicago Midway International Airport
- Fly from Aguadilla (BQN) to Chicago Midway International Airport (MDW)plane BQN - MDW
8h 34m$156–661Fly 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
7h 56m$177–630Fly 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$152–480
Ponce (PSE) to Chicago O'Hare International Airport (ORD) flights
Comparing Your Travel Options
The cheapest way to get from Puerto Rico to Chicago is to fly which costs $90 - $380 and takes 8h 40m.
The fastest way to get from Puerto Rico to Chicago is to fly which takes 7h 45m and costs $160 - $750.
The distance between Puerto Rico and Chicago is 2113 miles.
It takes approximately 8h 40m to get from Puerto Rico to Chicago, including transfers.
Chicago is 1h behind Puerto Rico. It is currently 8:35 PM in Puerto Rico and 7:35 PM in Chicago.
There are 1173+ hotels available in Chicago.
What companies run services between Puerto Rico and Chicago, IL, USA?
Frontier Airlines, JetBlue Airways, and United Airlines fly from Ponce (PSE) to Chicago O'Hare International Airport (ORD) twice daily.
- Website
- southwest.com
Flights from Ponce to Chicago Midway International Airport via Orlando
- Ave. Duration
- 7h 13m
- When
- Tuesday to Friday
- Estimated price
- $160–700
Flights from Ponce to Chicago Midway International Airport via Fort Lauderdale
- Ave. Duration
- 7h
- When
- Saturday
- Estimated price
- $160–700
Flights from Aguadilla to Chicago Midway International Airport via Orlando
- Ave. Duration
- 9h 55m
- When
- Every day
- Estimated price
- $150–650
Flights from Aguadilla to Chicago Midway International Airport via Fort Lauderdale
- Ave. Duration
- 9h 4m
- When
- Sunday
- Estimated price
- $160–650
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport
- Ave. Duration
- 4h 55m
- When
- Saturday
- Estimated price
- $120–550
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Tampa
- Ave. Duration
- 7h 45m
- When
- Monday, Thursday, and Friday
- Estimated price
- $130–550
- Website
- flyfrontier.com
Flights from Ponce to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 8h 20m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $190–480
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 7h 45m
- When
- Every day
- Estimated price
- $130–340
Flights from Ponce to Chicago Midway International Airport via Orlando
- Ave. Duration
- 11h 4m
- When
- Monday, Friday, and Sunday
- Estimated price
- $240–650
Flights from Aguadilla to Chicago Midway International Airport via Orlando
- Ave. Duration
- 9h 55m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $240–600
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 8h 44m
- When
- Every day
- Estimated price
- $190–480
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 9m
- When
- Every day
- Estimated price
- $140–370
- Website
- united.com
Flights from Ponce to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 7h 45m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $190–480
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 8h 7m
- When
- Every day
- Estimated price
- $90–370
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 26m
- When
- Every day
- Estimated price
- $95–400
- Website
- delta.com
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 9h 26m
- When
- Every day
- Estimated price
- $120–550
- Website
- aa.com
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 10h 22m
- When
- Every day
- Estimated price
- $90–370
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 36m
- When
- Every day
- Estimated price
- $95–400
- Website
- jetblue.com
Flights from Ponce to Chicago O'Hare International Airport via Fort Lauderdale
- Ave. Duration
- 11h 24m
- When
- Every day
- Estimated price
- $120–550
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