There are 9 ways to get from Riverhead to Chicago by train, plane, 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.
Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport
best- Take the train from Ronkonkoma to Jamaicatrain
- Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane JFK - ORD
6h 36m$527–1,251Train to Laguardia Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Ronkonkoma to Woodsidetrain
- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
7h 21m$87–345Train
- Take the train from Ronkonkoma to New York Penn Stationtrain Ronkonkoma Branch
- Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain Lake Shore Limited / ...
22h 46m$278–643Bus
- Take the bus from Riverhead to Airport Connection-Eastboundbus Brooklyn-North Fork
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
22h 47m$141–284Drive 864.4 mi
- Drive from Riverhead to Chicagocar 864.4 mi
14h 37m$158–228Train to Laguardia Airport, fly to Chicago Midway International Airport
- Take the train from Ronkonkoma to Woodsidetrain
- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
7h 7m$102–515Car ferry to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport
- Take the car ferry from Port Jefferson to Bridgeportcarferry
- Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane HVN - ORD
7h 2m$110–497Train, train to Westchester County Airport, fly to Chicago O'Hare International Airport
- Take the train from Riverhead to Ronkonkomatrain
- Take the train from Ronkonkoma 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
10h 5m$472–666Bus, train
- Take the bus from Riverhead LIRR to Brentwood LIRRbus 58
- Take the train from Brentwood to New York Penn Stationtrain
- Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
- Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
26h 44m$179–358
Riverhead to Chicago by train
Questions & Answers
The cheapest way to get from Riverhead to Chicago is to train and fly which costs $85 - $350 and takes 7h 21m.
The fastest way to get from Riverhead to Chicago is to train and fly which takes 6h 36m and costs $500 - $1,300.
No, there is no direct bus from Riverhead to Chicago station. However, there are services departing from Riverhead LIRR and arriving at Chicago Bus Station via Riverhead, 188 St/64 Av and New York Midtown. The journey, including transfers, takes approximately 22h 47m.
No, there is no direct train from Riverhead to Chicago station. However, there are services departing from Riverhead and arriving at Chicago Union Station via Ronkonkoma and Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 22h 46m.
The distance between Riverhead and Chicago is 830 miles. The road distance is 869.4 miles.
The best way to get from Riverhead to Chicago without a car is to train which takes 22h 46m and costs $270 - $650.
It takes approximately 6h 36m to get from Riverhead to Chicago, including transfers.
Riverhead to Chicago bus services, operated by Hampton Jitney Inc., depart from Riverhead station.
Riverhead to Chicago train services, operated by Long Island Rail Road, depart from Ronkonkoma station.
The best way to get from Riverhead to Chicago is to train which takes 22h 46m and costs $270 - $650. Alternatively, you can bus, which costs $140 - $290 and takes 22h 47m.
What companies run services between Riverhead, NY, USA and Chicago, IL, USA?
You can take a train from Riverhead to Chicago Union Station via Ronkonkoma, Penn Station, and Ny Moynihan Train Hall At Penn Station in around 22h 46m. Alternatively, you can take a bus from Riverhead LIRR to Chicago Bus Station via Riverhead, Airport Connection-Eastbound, 188 St/64 Av, 6 Av/W 37 St, and New York Midtown in around 22h 47m.
- Website
- aa.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 57m
- When
- Every day
- Estimated price
- $55–320
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 52m
- When
- Every day
- Estimated price
- $70–380
Flights from Westchester County Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 44m
- When
- Every day
- Estimated price
- $85–460
Flights from Westchester County Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 29m
- When
- Every day
- Estimated price
- $90–490
Flights from Westchester County Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 5h 21m
- When
- Every day
- Estimated price
- $120–600
- Website
- delta.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $55–320
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 5m
- When
- Every day
- Estimated price
- $55–320
Flights from Laguardia Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $85–460
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 52m
- When
- Every day
- Estimated price
- $70–380
Flights from Westchester County Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 58m
- When
- Every day
- Estimated price
- $85–460
- Website
- united.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 43m
- When
- Every day
- Estimated price
- $70–380
- Website
- southwest.com
Flights from Laguardia Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $80–460
- Website
- jetblue.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 52m
- When
- Every day
- Estimated price
- $55–320
- Website
- aveloair.com
Flights from Tweed-New Haven Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 53m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $80–400
- Phone
- +1-718-217-5477
- Website
- mta.info
Train from Ronkonkoma to Jamaica
- Ave. Duration
- 58 min
- Frequency
- Every 15 minutes
- Estimated price
- $8–21
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $8–12
- Peak
- $16–21
Train from Ronkonkoma to New York Penn Station
- Ave. Duration
- 1h 20m
- Frequency
- Every 20 minutes
- Estimated price
- $10–27
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $10–15
- Peak
- $21–27
Train from Ronkonkoma to Woodside
- Ave. Duration
- 1h 9m
- Frequency
- Every 20 minutes
- Estimated price
- $9–24
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $9–13
- Peak
- $19–24
Train from Riverhead to Ronkonkoma
- Ave. Duration
- 46 min
- Frequency
- Every 3 hours
- Estimated price
- $8–17
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $8–12
- Peak
- $11–17
Train from Ronkonkoma to Grand Central Terminal
- Ave. Duration
- 1h 20m
- Frequency
- Hourly
- Estimated price
- $10–27
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $10–15
- Peak
- $21–27
Train from Brentwood to New York Penn Station
- Ave. Duration
- 1h 8m
- Frequency
- Every 20 minutes
- Estimated price
- $12–26
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $12–17
- Peak
- $19–26
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station
- Ave. Duration
- 19h 32m
- Frequency
- Once daily
- Estimated price
- $260–600
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 877.690.5114
- Website
- mta.info
Train from Grand Central Terminal to White Plains
- Ave. Duration
- 52 min
- Frequency
- Every 20 minutes
- Estimated price
- $9–15
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $9–11
- Peak
- $13–15
- Phone
- +1 631.283.4600
- Website
- hamptonjitney.com
Bus from Riverhead to Airport Connection-Eastbound
- Ave. Duration
- 2h 32m
- Frequency
- On demand
- Estimated price
- $27–75
- Website
- https://www.hamptonjitney.com/hjmobile/
- Schedules at
- https://www.hamptonjitney.com/booking/jitney/schedules.php
- Book at
- https://www.hamptonjitney.com/booking/jitney/tripfinder.php
- Onboard
- $35–50
- Ambassador
- $60–75
- Prepaid Online Rate
- $27–35
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $110–200
- Schedules at
- flixbus.com
- Phone
- 631 852 5200
- buses@suffolkcountyny.gov
- Website
- sctbus.org
Bus from Riverhead LIRR to Brentwood LIRR
- Ave. Duration
- 1h 45m
- Frequency
- Hourly
- Estimated price
- $3
- Schedules at
- sctbus.org
- Adults
- $3
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Port Authority Bus Terminal to Baltimore Downtown Bus Station
- Ave. Duration
- 3h 15m
- Frequency
- Every 3 hours
- Estimated price
- $35–75
- Website
- https://www.greyhound.com/
Bus from Baltimore Downtown Bus Station to Chicago Bus Station
- Ave. Duration
- 18h 40m
- Frequency
- Twice daily
- Estimated price
- $120–230
- Website
- https://www.greyhound.com/
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Port Authority Bus Terminal to Baltimore Downtown Bus Station
- Ave. Duration
- 3h 45m
- Frequency
- Every 2 hours
- Estimated price
- $45–100
- Website
- https://peterpanbus.com
- Phone
- +1 888-443-3779
- info@PJferry.com
- Website
- 88844ferry.com
Car ferry from Port Jefferson to Bridgeport
- Ave. Duration
- 1h 15m
- Frequency
- Hourly
- Estimated price
- $20–80
- Website
- https://www.88844ferry.com
- Schedules at
- https://www.88844ferry.com/schedule
- Car and passenger
- $70–80
- Adult
- $23
- Senior
- $20
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More Questions & Answers
Riverhead to Chicago bus services, operated by Hampton Jitney Inc., arrive at Airport Connection-Eastbound station.
Chicago is 1h behind Riverhead. It is currently 11:30 PM in Riverhead and 10:30 PM in Chicago.
Riverhead to Chicago train services, operated by Long Island Rail Road, arrive at New York Penn Station.
Yes, the driving distance between Riverhead to Chicago is 869 miles. It takes approximately 14h 37m to drive from Riverhead to Chicago.
There are 1326+ hotels available in Chicago.





















