There are 8 ways to get from Long Island to Chicago by plane, bus (Flixbus), train (Amtrak), 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
2h 56m$206–633Bus (Flixbus)
cheapest- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
18h 21m$123–213Train (Amtrak)
- Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain Lake Shore Limited / ...
20h 54m$253–603Drive 794.3 mi
- Drive from Brooklyn to Chicagocar 794.3 mi
13h 22m$145–210Fly Laguardia Airport to Chicago O'Hare International Airport
- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
3h 9m$137–556Fly 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 29m$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 14m$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 9m$133–268
Long Island to Chicago by bus and train (Flixbus)
Questions & Answers
The cheapest way to get from Long Island to Chicago is to bus which costs $120 - $220 and takes 18h 21m.
The fastest way to get from Long Island to Chicago is to fly which takes 2h 56m 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 18h 21m.
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 738 miles. The road distance is 798.9 miles.
The best way to get from Long Island to Chicago without a car is to bus which takes 18h 21m and costs $120 - $220.
It takes approximately 2h 56m 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 2h 56m and costs $200 - $650. Alternatively, you can bus, which costs $120 - $220 and takes 18h 21m, you could also train, which costs $250 - $650 and takes 20h 54m.
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, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $120–200 and the journey takes 16h 55m.
- Website
- united.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $80–430
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 44m
- When
- Every day
- Estimated price
- $65–350
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Columbus
- Ave. Duration
- 4h 13m
- When
- Saturday
- Estimated price
- $65–350
Flights from Newark Liberty International Airport to Chicago O'Hare International Airport via Buffalo
- Ave. Duration
- 4h 15m
- When
- Every day
- Estimated price
- $65–350
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
- $250–600
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $120–200
- 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.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
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 11:45 PM in Long Island and 10:45 PM 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 1305+ hotels available in Chicago.