There are 10 ways to get from Chicago to Westhampton Beach by plane, train, train (Amtrak), bus (Flixbus), car, car ferry, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Laguardia Airport, train
best- Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane MDW - LGA
- Take the train from Jamaica to Westhamptontrain
7h 9m$260–733Fly Chicago O'Hare International Airport to Westchester County Airport, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane ORD - HPN
- Take the train from White Plains to Grand Central Terminaltrain
- Take the train from Grand Central Terminal to Jamaicatrain
- Take the train from Jamaica to Westhamptontrain
10h 6m$120–432Train
- Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain Lake Shore Limited / ...
- Take the train from New York Penn Station to Westhamptontrain Montauk Branch
23h 28m$574–889Bus
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2640 / ...
- Take the bus from 86th St & Broadway to Westhamptonbus WESTHAMPTON-Westbound
23h 35m$219–344Drive 865.9 mi
- Drive from Chicago to Westhampton Beachcar 865.9 mi
14h 44m$153–221Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane ORD - JFK
- Take the train from Jamaica to Westhamptontrain
7h 9m$406–939Fly Chicago O'Hare International Airport to Laguardia Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane ORD - LGA
- Take the train from Jamaica to Westhamptontrain
7h 28m$170–553Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane ORD - EWR
- Take the train from New York Penn Station to Westhamptontrain
7h 53m$182–764Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, car ferry, drive
- Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane ORD - HVN
- Take the carferry from Bridgeport to Port Jeffersoncarferry
- Drive from Port Jefferson to Westhampton Beachcar
7h 8m$174–549Bus, train
- Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus
- Take the bus from Baltimore to New Yorkbus
- Take the train from Jamaica to Westhamptontrain
25h 51m$232–369
Chicago Midway International Airport (MDW) to Laguardia Airport (LGA) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Westhampton Beach is to drive which costs $150 - $230 and takes 14h 44m.
The fastest way to get from Chicago to Westhampton Beach is to fly and car ferry and drive which takes 7h 8m and costs $170 - $550.
No, there is no direct bus from Chicago station to Westhampton Beach. However, there are services departing from Chicago Bus Station and arriving at Westhampton via 86th St & Broadway. The journey, including transfers, takes approximately 23h 35m.
No, there is no direct train from Chicago station to Westhampton Beach. However, there are services departing from Chicago Union Station and arriving at Westhampton via New York Penn Station. The journey, including transfers, takes approximately 23h 28m.
The distance between Chicago and Westhampton Beach is 814 miles. The road distance is 871 miles.
The best way to get from Chicago to Westhampton Beach without a car is to train which takes 23h 28m and costs $550 - $900.
It takes approximately 7h 9m to get from Chicago to Westhampton Beach, including transfers.
Chicago to Westhampton Beach bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Westhampton Beach train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Westhampton Beach is to train which takes 23h 28m and costs $550 - $900. Alternatively, you can bus, which costs $210 - $350 and takes 23h 35m.
What companies run services between Chicago, IL, USA and Westhampton Beach, NY, USA?
You can take a train from Chicago Union Station to Westhampton Beach via Ny Moynihan Train Hall At Penn Station, New York Penn Station, and Westhampton in around 23h 28m. Alternatively, you can take a bus from Chicago Bus Station to Westhampton Beach via New York Midtown, 34 St-Penn Station, 86 St, 86th St & Broadway, and Westhampton in around 23h 35m.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to John F. Kennedy International Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $45–250
Flights from Chicago O'Hare International Airport to John F. Kennedy International Airport via Cleveland
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $45–250
Flights from Chicago O'Hare International Airport to John F. Kennedy International Airport via Pittsburgh
- Ave. Duration
- 5h 20m
- When
- Tuesday and Wednesday
- Estimated price
- $45–250
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $80–450
Flights from Chicago O'Hare International Airport to Newark Liberty International Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $50–270
Flights from Chicago O'Hare International Airport to Westchester County Airport
- Ave. Duration
- 2h 16m
- When
- Every day
- Estimated price
- $60–330
Flights from Chicago O'Hare International Airport to Westchester County Airport via Reagan Washington
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $65–340
Flights from Chicago O'Hare International Airport to Westchester County Airport via Charlotte
- Ave. Duration
- 5h 27m
- When
- Every day
- Estimated price
- $80–390
- Website
- united.com
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 17m
- When
- Every day
- Estimated price
- $80–450
Flights from Chicago O'Hare International Airport to Newark Liberty International Airport
- Ave. Duration
- 2h 16m
- When
- Every day
- Estimated price
- $50–270
Flights from Chicago O'Hare International Airport to Newark Liberty International Airport via Pittsburgh
- Ave. Duration
- 4h 3m
- When
- Every day
- Estimated price
- $50–270
- Website
- delta.com
Flights from Chicago O'Hare International Airport to John F. Kennedy International Airport
- Ave. Duration
- 2h 27m
- When
- Every day
- Estimated price
- $45–250
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $80–450
Flights from Chicago O'Hare International Airport to Newark Liberty International Airport via Detroit
- Ave. Duration
- 4h 3m
- When
- Every day
- Estimated price
- $50–270
- Website
- southwest.com
Flights from Chicago Midway International Airport to Laguardia Airport
- Ave. Duration
- 2h 4m
- When
- Every day
- Estimated price
- $130–750
- Website
- aveloair.com
Flights from Chicago O'Hare International Airport to Tweed-New Haven Airport
- Ave. Duration
- 2h 20m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–450
- Phone
- +1-718-217-5477
- Website
- Long Island Rail Road
Train from Jamaica to Westhampton
- Ave. Duration
- 1h 49m
- Frequency
- Every 4 hours
- Estimated price
- $16–40
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $16–23
- Peak
- $28–40
Train from New York Penn Station to Westhampton
- Ave. Duration
- 2h 13m
- Frequency
- 6 times a week
- Estimated price
- $19–45
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $19–26
- Peak
- $30–45
Train from Jamaica to Westhampton
- Ave. Duration
- 1h 49m
- Frequency
- Every 4 hours
- Estimated price
- $16–40
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $16–23
- Peak
- $28–40
Train from Jamaica to Westhampton
- Ave. Duration
- 1h 49m
- Frequency
- Every 4 hours
- Estimated price
- $16–40
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $16–23
- Peak
- $28–40
Train from New York Penn Station to Westhampton
- Ave. Duration
- 2h 13m
- Frequency
- 6 times a week
- Estimated price
- $19–45
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $19–26
- Peak
- $30–45
Train from Grand Central Terminal to Jamaica
- Ave. Duration
- 21 min
- Frequency
- Every 15 minutes
- Estimated price
- $5–9
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $5–8
- Peak
- $5–9
Train from Jamaica to Westhampton
- Ave. Duration
- 1h 49m
- Frequency
- Every 4 hours
- Estimated price
- $13–35
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $13–19
- Peak
- $27–35
Train from Jamaica to Westhampton
- Ave. Duration
- 1h 49m
- Frequency
- Every 4 hours
- Estimated price
- $16–40
- Website
- Long Island Rail Road
- Schedules at
- Long Island Rail Road Schedules
- Off-Peak
- $16–23
- Peak
- $28–40
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 20h 12m
- Frequency
- Once daily
- Estimated price
- $500–850
- Website
- Amtrak
- Phone
- +1 877.690.5114
- Website
- Metro North Railroad
Train from White Plains to Grand Central Terminal
- Ave. Duration
- 55 min
- Frequency
- Every 20 minutes
- Estimated price
- $9–15
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $9–11
- Peak
- $13–15
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Twice daily
- Estimated price
- $160–240
- Schedules at
- Flixbus USA
- Phone
- +1 631.283.4600
- Website
- Hampton Jitney
Bus from 86th St & Broadway to Westhampton
- Ave. Duration
- 2h 2m
- Frequency
- 5 times a day
- Estimated price
- $29–75
- Website
- Hampton Jitney
- Schedules at
- Hampton Jitney Schedule Information
- Book at
- Hampton Jitney Reservations
- Onboard
- $40–50
- Ambassador
- $60–75
- Prepaid Online Rate
- $29–40
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Baltimore Downtown Bus Station
- Ave. Duration
- 17h 45m
- Frequency
- Twice daily
- Estimated price
- $140–210
- Website
- Greyhound
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from Baltimore to New York
- Ave. Duration
- 3h 44m
- Frequency
- Hourly
- Estimated price
- $45–85
- Website
- Peter Pan
- Phone
- +1 888-443-3779
- [email protected]
- Website
- Bridgeport-Port Jefferson Ferry
Car ferry from Bridgeport to Port Jefferson
- Ave. Duration
- 1h 15m
- Frequency
- Hourly
- Estimated price
- $22–80
- Website
- Bridgeport-Port Jefferson Ferry
- Schedules at
- Ferry Schedule
- Car and passenger
- $78–80
- Adult
- $25
- Senior
- $22
Want to know more about travelling around United States
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Booking & Getting There
Chicago to Westhampton Beach bus services, operated by Flixbus USA, arrive at New York Midtown station.
Westhampton Beach is 1h ahead of Chicago. It is currently 12:50 AM in Chicago and 1:50 AM in Westhampton Beach.
Chicago to Westhampton Beach train services, operated by Amtrak, arrive at Ny Moynihan Train Hall At Penn Station.
Yes, the driving distance between Chicago to Westhampton Beach is 871 miles. It takes approximately 14h 44m to drive from Chicago to Westhampton Beach.
There are 146+ hotels available in Westhampton Beach.



















