There are 10 ways to get from Islip to Chicago by train, plane, train (Amtrak), bus, or car
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 Islip to Jamaicatrain
- Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane JFK - ORD
5h 41m$820–1,035Train to Laguardia Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Islip to Jamaicatrain
- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
5h 55m$64–279Train
- Take the train from Babylon to New York Penn Stationtrain Babylon Branch / ...
- Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain Lake Shore Limited / ...
22h 18m$132–506Train, bus
- Take the train from Amityville to New York Penn Stationtrain Babylon Branch
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640
23h 27m$101–243Drive 836.1 mi
- Drive from Islip to Chicagocar 836.1 mi
14h 5m$153–221Train to Laguardia Airport, fly to Chicago Midway International Airport
- Take the train from Islip to Jamaicatrain
- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
5h 39m$99–489Train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport
- Take the train from Islip to Jamaicatrain
- Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane EWR - ORD
6h 17m$83–360Train, train to Westchester County Airport, fly to Chicago O'Hare International Airport
- Take the train from Islip to Jamaicatrain
- 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
8h 23m$85–390Train to Laguardia Airport, fly to General Mitchell International Airport, train
- Take the train from Islip to Jamaicatrain
- Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane LGA - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
8h 10m$226–694Train, bus via Baltimore
- Take the train from Babylon 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
25h 28m$117–291
Islip to Chicago by bus and train
Questions & Answers
The cheapest way to get from Islip to Chicago is to train and fly which costs $60 - $280 and takes 5h 55m.
The fastest way to get from Islip to Chicago is to train and fly which takes 5h 39m and costs $95 - $490.
The distance between Islip and Chicago is 799 miles. The road distance is 840.9 miles.
The best way to get from Islip to Chicago without a car is to train which takes 22h 18m and costs $130 - $550.
It takes approximately 5h 41m to get from Islip to Chicago, including transfers.
Chicago is 1h behind Islip. It is currently 12:38 PM in Islip and 11:38 AM in Chicago.
Yes, the driving distance between Islip to Chicago is 841 miles. It takes approximately 14h 5m to drive from Islip to Chicago.
There are 1068+ hotels available in Chicago.
What companies run services between Islip, NY, USA and Chicago, IL, USA?
You can take a bus from Islip Town Hall to Chicago Union Station via Babylon LIRR, Babylon, Penn Station, and Ny Moynihan Train Hall At Penn Station in around 22h 18m.
- 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
- $50–290
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Columbus
- Ave. Duration
- 5h 28m
- When
- Tuesday, Wednesday, and Saturday
- Estimated price
- $55–300
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Pittsburgh
- Ave. Duration
- 6h 2m
- When
- Tuesday
- Estimated price
- $50–290
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 54m
- When
- Every day
- Estimated price
- $60–330
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $50–280
Flights from Westchester County Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 49m
- When
- Every day
- Estimated price
- $60–340
Flights from Westchester County Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 48m
- When
- Every day
- Estimated price
- $65–360
Flights from Westchester County Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 5h 39m
- When
- Every day
- Estimated price
- $80–410
Flights from Laguardia Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 59m
- When
- Every day
- Estimated price
- $160–850
- Website
- united.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $60–330
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 47m
- When
- Every day
- Estimated price
- $50–280
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Cleveland
- Ave. Duration
- 4h 33m
- When
- Saturday
- Estimated price
- $50–280
Flights from Laguardia Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 47m
- When
- Every day
- Estimated price
- $160–850
- Website
- delta.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $50–290
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 4m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $50–290
Flights from Laguardia Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 8m
- When
- Every day
- Estimated price
- $85–470
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $60–330
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $50–280
Flights from Westchester County Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 57m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $60–340
Flights from Laguardia Airport to General Mitchell International Airport
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $150–850
Flights from Laguardia Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 20m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $150–850
- Website
- southwest.com
Flights from Laguardia Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $85–460
Flights from Laguardia Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 45m
- When
- Monday, Thursday, and Friday
- Estimated price
- $160–850
- Website
- spirit.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $50–250
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 37m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $50–290
- Website
- jetblue.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 11m
- When
- Every day
- Estimated price
- $50–290
- Website
- flyfrontier.com
Flights from John F. Kennedy International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h
- When
- Monday, Wednesday, Friday, and Saturday
- Estimated price
- $50–290
- Phone
- +1-718-217-5477
- Website
- mta.info
Train from Islip to Jamaica
- Ave. Duration
- 51 min
- Frequency
- Hourly
- Estimated price
- $9–21
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $9–13
- Peak
- $13–21
Train from Babylon to New York Penn Station
- Ave. Duration
- 1h 12m
- Frequency
- Every 15 minutes
- Estimated price
- $10–24
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $10–15
- Peak
- $15–24
Train from Amityville to New York Penn Station
- Ave. Duration
- 1h 1m
- Frequency
- Every 15 minutes
- Estimated price
- $9–21
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $9–13
- Peak
- $13–21
Train from Jamaica to Grand Central Terminal
- Ave. Duration
- 20 min
- Frequency
- Every 10 minutes
- Estimated price
- $2–6
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $2–4
- Peak
- $3–6
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
- $120–480
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–40
- 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
- 50 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 (855) 626-8585
- Website
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Once daily
- Estimated price
- $90–220
- Schedules at
- flixbus.com
- 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
- $30–75
- Website
- https://www.greyhound.com/
Bus from Baltimore Downtown Bus Station to Chicago Bus Station
- Ave. Duration
- 18h 40m
- Frequency
- Twice daily
- Estimated price
- $75–190
- 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
- $30–65
- Website
- https://peterpanbus.com
- Adult
- $30–65
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