There are 10 ways to get from Jamaica to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly John F. Kennedy International Airport to Chicago O'Hare International Airport
best- Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane JFK - ORD
4h 36m$321–864Train, train to Westchester County Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Jamaica to Grand Central Terminaltrain
- Take the train from Grand Central Terminal to White Plainstrain
- Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane HPN - ORD
7h 20m$114–582Train (Amtrak)
- Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain Lake Shore Limited / ...
20h 52m$235–559Bus (Flixbus)
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640 / ...
21h 45m$145–239Drive 799.2 mi
- Drive from Jamaica to Chicagocar 799.2 mi
13h 29m$146–211Fly Laguardia Airport to Chicago O'Hare International Airport
- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
5h 10m$138–566Fly Laguardia Airport to Chicago Midway International Airport
- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
5h$208–666Fly Newark Liberty International Airport to Chicago O'Hare International Airport
- Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane EWR - ORD
5h 25m$148–892Train to Philadelphia International Airport, fly to Chicago Midway International Airport
- Take the train from Ny Moynihan Train Hall At Penn Station to 30th Street Stationtrain
- Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane PHL - MDW
6h 17m$169–988Bus via Baltimore (Greyhound)
- Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus Greyhound US0670 / ...
- Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus Greyhound US0164
24h 54m$148–253
Jamaica to Chicago by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Jamaica to Chicago is to drive which costs $140 - $220 and takes 13h 29m.
The fastest way to get from Jamaica to Chicago is to fly which takes 4h 36m and costs $320 - $900.
No, there is no direct bus from Jamaica to Chicago station. However, there are services departing from New York Midtown and arriving at Chicago Bus Station via . The journey, including transfers, takes approximately 21h 45m.
No, there is no direct train from Jamaica to Chicago station. However, there are services departing from Jamaica and arriving at Chicago Union Station via Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 20h 52m.
The distance between Jamaica and Chicago is 765 miles. The road distance is 803.9 miles.
The best way to get from Jamaica to Chicago without a car is to train which takes 20h 52m and costs $230 - $600.
It takes approximately 4h 36m to get from Jamaica to Chicago, including transfers.
Jamaica to Chicago bus services, operated by Flixbus USA, depart from New York Midtown station.
Jamaica to Chicago train services, operated by Amtrak, depart from Ny Moynihan Train Hall At Penn Station.
The best way to get from Jamaica to Chicago is to fly which takes 4h 36m and costs $320 - $900. Alternatively, you can train, which costs $230 - $600 and takes 20h 52m, you could also bus, which costs $140 - $240 and takes 21h 45m.
What companies run services between Jamaica, NY, USA and Chicago, IL, USA?
American Airlines, JetBlue Airways, and Delta fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $230–550 and the journey takes 19h 32m.
- Website
- aa.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 51m
- When
- Every day
- Estimated price
- $55–300
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Pittsburgh
- Ave. Duration
- 4h 40m
- When
- Every day
- Estimated price
- $55–300
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Cleveland
- Ave. Duration
- 5h 13m
- When
- Every day
- Estimated price
- $55–300
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Columbus
- Ave. Duration
- 5h 15m
- When
- Every day
- Estimated price
- $55–310
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $75–410
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 41m
- When
- Every day
- Estimated price
- $60–330
Flights from Westchester County Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $95–550
Flights from Westchester County Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 25m
- When
- Every day
- Estimated price
- $100–550
Flights from Westchester County Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 5h 3m
- When
- Every day
- Estimated price
- $130–650
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station
- Ave. Duration
- 19h 32m
- Frequency
- Once daily
- Estimated price
- $230–550
- Website
- Amtrak
Train from Ny Moynihan Train Hall At Penn Station to 30th Street Station
- Ave. Duration
- 1h 21m
- Frequency
- Every 30 minutes
- Estimated price
- $22–55
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $140–230
- Schedules at
- Flixbus USA
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Booking & Getting There
Jamaica to Chicago bus services, operated by Flixbus USA, arrive at Chicago Bus Station.
Chicago is 1h behind Jamaica. It is currently 8:40 AM in Jamaica and 7:40 AM in Chicago.
Jamaica to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Jamaica to Chicago is 804 miles. It takes approximately 13h 29m to drive from Jamaica to Chicago.
There are 1280+ hotels available in Chicago.