There are 8 ways to get from Long Island to Chicago by plane, train (Amtrak), bus (Flixbus), car, 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 Laguardia Airport to Chicago Midway International Airport
best- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
3h 11m$88–465Fly Laguardia Airport to Chicago O'Hare International Airport
cheapest- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
3h 27m$52–249Train (Amtrak)
- Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain Lake Shore Limited / ...
20h 56m$123–483Bus (Flixbus)
- Take the bus from New York City Chinatown to Chicago Bus Stationbus FlixBus N2640
22h 21m$93–227Drive 794.3 mi
- Drive from Brooklyn to Chicagocar 794.3 mi
13h 21m$145–210Fly John F. Kennedy International Airport to Chicago O'Hare International Airport
- Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane JFK - ORD
3h 38m$849–996Fly 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 24m$75–336Bus via Baltimore
- 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
23h 42m$108–268
Long Island to Chicago by subway, foot, and train (Amtrak)
Questions & Answers
The cheapest way to get from Long Island to Chicago is to fly which costs $50 - $250 and takes 3h 27m.
The fastest way to get from Long Island to Chicago is to fly which takes 3h 11m and costs $85 - $470.
No, there is no direct bus from Long Island to Chicago station. However, there are services departing from Cherry St/Jackson St and arriving at Chicago Bus Station via New York City Chinatown. The journey, including transfers, takes approximately 22h 21m.
No, there is no direct train from Long Island to Chicago station. However, there are services departing from Queens Plaza and arriving at Chicago Union Station via Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 20h 56m.
The distance between Long Island and Chicago is 738 miles. The road distance is 798.9 miles.
The best way to get from Long Island to Chicago without a car is to train which takes 20h 56m and costs $120 - $490.
It takes approximately 3h 11m to get from Long Island to Chicago, including transfers.
Long Island to Chicago bus services, operated by Flixbus USA, depart from New York City Chinatown station.
Long Island to Chicago train services, operated by Amtrak, depart from Ny Moynihan Train Hall At Penn Station.
The best way to get from Long Island to Chicago is to fly which takes 3h 11m and costs $85 - $470. Alternatively, you can train, which costs $120 - $490 and takes 20h 56m, you could also bus, which costs $90 - $230 and takes 22h 21m.
What companies run services between Long Island, Suffolk County, NY, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $120–480 and the journey takes 19h 32m.
- 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
- Website
- aa.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 54m
- When
- Every day
- Estimated price
- $60–330
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 Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $50–280
- Website
- delta.com
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 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 Newark Liberty International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $50–280
- Website
- southwest.com
Flights from Laguardia Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $85–460
- 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, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $50–290
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
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from New York City Chinatown to Chicago Bus Station
- Ave. Duration
- 21h 10m
- Frequency
- Once daily
- Estimated price
- $90–220
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- 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
Want to know more about travelling around United States
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More Questions & Answers
Long Island to Chicago bus services, operated by Flixbus USA, arrive at Chicago Bus Station.
Chicago is 1h behind Long Island. It is currently 11:37 AM in Long Island and 10:37 AM in Chicago.
Long Island to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Long Island to Chicago is 799 miles. It takes approximately 13h 21m to drive from Long Island to Chicago.
There are 1068+ hotels available in Chicago.