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 Aguadilla to Chicago O'Hare International Airport
best- Fly from Aguadilla (BQN) to Chicago O'Hare International Airport (ORD)plane BQN - ORD
8h 30m$126–511Fly 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$88–376Fly Ponce to Chicago Midway International Airport
- Fly from Ponce (PSE) to Chicago Midway International Airport (MDW)plane PSE - MDW
8h 31m$173–756Fly Aguadilla to Chicago Midway International Airport
- Fly from Aguadilla (BQN) to Chicago Midway International Airport (MDW)plane BQN - MDW
8h 19m$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 16m$152–490Fly 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$187–680
Aguadilla (BQN) 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 $85 - $380 and takes 8h 40m.
The fastest way to get from Puerto Rico to Chicago is to fly which takes 7h 56m and costs $180 - $700.
The distance between Puerto Rico and Chicago is 2083 miles.
It takes approximately 8h 30m to get from Puerto Rico to Chicago, including transfers.
Chicago is 2h behind Puerto Rico. It is currently 3:14 AM in Puerto Rico and 1:14 AM in Chicago.
There are 1309+ hotels available in Chicago.
What companies run services between Puerto Rico and Chicago, IL, USA?
Frontier Airlines, United Airlines, and two other airlines fly from Aguadilla (BQN) to Chicago O'Hare International Airport (ORD) every 4 hours.
- Website
- southwest.com
Flights from Ponce to Chicago Midway International Airport via Orlando
- Ave. Duration
- 7h 41m
- When
- Monday
- Estimated price
- $270–700
Flights from Ponce to Chicago Midway International Airport via Fort Lauderdale
- Ave. Duration
- 8h 49m
- When
- Saturday
- Estimated price
- $170–750
Flights from Aguadilla to Chicago Midway International Airport via Orlando
- Ave. Duration
- 7h 5m
- When
- Saturday
- Estimated price
- $170–750
Flights from Aguadilla to Chicago Midway International Airport via Fort Lauderdale
- Ave. Duration
- 8h 49m
- When
- Saturday
- Estimated price
- $170–750
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport
- Ave. Duration
- 4h 55m
- When
- Saturday
- Estimated price
- $130–600
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 7h 5m
- When
- Saturday
- Estimated price
- $140–600
Flights from Luis Munoz Marin International Airport to Chicago Midway International Airport via Tampa
- Ave. Duration
- 8h 32m
- When
- Monday, Thursday, Friday, Sunday, Tuesday, and Wednesday
- Estimated price
- $140–600
- Website
- flyfrontier.com
Flights from Aguadilla to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 7h 10m
- When
- Tuesday and Wednesday
- 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
- $140–350
Flights from Ponce to Chicago Midway International Airport via Orlando
- Ave. Duration
- 10h 53m
- When
- Monday and Friday
- Estimated price
- $270–700
Flights from Aguadilla to Chicago Midway International Airport via Orlando
- Ave. Duration
- 9h 50m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $270–700
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 9m
- When
- Every day
- Estimated price
- $150–390
- Website
- united.com
Flights from Aguadilla to Chicago O'Hare International Airport via Newark
- Ave. Duration
- 8h 39m
- When
- Every day
- Estimated price
- $120–550
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 9h 7m
- When
- Every day
- Estimated price
- $85–370
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 26m
- When
- Every day
- Estimated price
- $95–410
- Website
- jetblue.com
Flights from Aguadilla to Chicago O'Hare International Airport via Fort Lauderdale
- Ave. Duration
- 10h 26m
- When
- Every day
- Estimated price
- $120–550
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Fort Lauderdale
- Ave. Duration
- 8h 41m
- When
- Every day
- Estimated price
- $100–420
- Website
- aa.com
Flights from Aguadilla to Chicago O'Hare International Airport via Orlando
- Ave. Duration
- 7h 19m
- When
- Every day
- Estimated price
- $120–500
Flights from Eugenio María De Hostos Airport to Chicago O'Hare International Airport via Luis Munoz Marin International Airport
- Ave. Duration
- 8h 8m
- When
- Every day
- Estimated price
- $85–370
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 5h 38m
- When
- Every day
- Estimated price
- $95–410
- Website
- arajet.com
Flights from Luis Munoz Marin International Airport to Chicago O'Hare International Airport via Punta Cana
- Ave. Duration
- 8h 40m
- When
- Thursday
- Estimated price
- $160–650
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