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 O'Hare International Airport
best- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
3h 11m$137–556Train (Amtrak)
- Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain Lake Shore Limited / ...
20h 54m$233–603Bus (Flixbus)
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640 / ...
21h 52m$143–233Drive 794.3 mi
- Drive from Brooklyn to Chicagocar 794.3 mi
13h 22m$145–210Fly Laguardia Airport to Chicago Midway International Airport
- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
3h 1m$206–633Fly 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 27m$319–831Fly 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 23m$146–886Bus 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 34m$148–253
Long Island to Chicago by subway and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Long Island to Chicago is to drive which costs $140 - $210 and takes 13h 22m.
The fastest way to get from Long Island to Chicago is to fly which takes 3h 1m and costs $200 - $650.
No, there is no direct bus from Long Island to Chicago station. However, there are services departing from Broadway/75 St and arriving at Chicago Bus Station via New York Midtown. The journey, including transfers, takes approximately 21h 52m.
No, there is no direct train from Long Island to Chicago station. However, there are services departing from Atlantic Av-Barclays Ctr and arriving at Chicago Union Station via Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 20h 54m.
The distance between Long Island and Chicago is 754 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 54m and costs $230 - $650.
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 Midtown 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 $130 - $600. Alternatively, you can train, which costs $230 - $650 and takes 20h 54m, you could also bus, which costs $140 - $240 and takes 21h 52m.
What companies run services between Long Island, Suffolk County, NY, USA and Chicago, IL, USA?
American Airlines, Delta, and United Airlines fly from Laguardia Airport (LGA) 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 $230–600 and the journey takes 19h 32m.
- Website
- united.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $75–410
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $60–330
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Buffalo
- Ave. Duration
- 4h 15m
- When
- Every day
- Estimated price
- $60–340
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Grand Rapids
- Ave. Duration
- 4h 29m
- When
- Every day
- Estimated price
- $60–340
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 36m
- When
- Every day
- Estimated price
- $60–330
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
- $230–600
- 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
- $140–220
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
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Booking & Getting There
Long Island to Chicago bus services, operated by Flixbus USA, arrive at Chicago Bus Station.
Chicago is 1h behind Long Island. It is currently 3:08 AM in Long Island and 2:08 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 22m to drive from Long Island to Chicago.
There are 1301+ hotels available in Chicago.