Next departures for New York City to Chicago on November 19
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Cheapest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 20
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
Cheapest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 21
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Cheapest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 22
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
Cheapest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 23
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
Cheapest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 24
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
Cheapest
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 25
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Cheapest
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Next departures for New York City to Chicago on November 26
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Cheapest
NYC Midtown (31st St & 8th Ave)
Chicago 95Th & Dan Ryan
Fastest
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Penn Station, Moynihan Train Hall
Chicago (Union Station), IL
No tags
NYC Midtown (31st St & 8th Ave)
Downtown Greyhound Station
No tags
Last refresh of the prices: Today at 6:35 AM EST.
Compare 2 ways to go from New York Penn Station to Chicago
We recommend taking the bus
Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 36 minutes and with fares starting at just $87, it presents an excellent value for a comfortable ride.
Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
FlixBus New York City Chicago recent customer reviews
I got left at a Pilot gas station in PA not happy! I had to take a Uber to a bus station to purchase another ticket 🙃 to Chicago.
1 out of 5 stars
Elianne L.
Big delays, almost 0 communication, estimates of delays not accurate at all, missed connection because of delay. Stuck in different city, had to pay for a hotel, also lost money on a hotel i booked at my final destination. Extremely tiresd after sleepless 24hours with no water or food.
Based on 5593 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $79
Amtrak New York City Chicago recent customer reviews
The communication from the workers was terrible. A lot of rude and snotty people in NY and in Chicago. The ride was smooth and went well.
Frequently asked questions about traveling from New York City to Chicago by bus
How much does a bus ticket from New York Penn Station to Chicago cost?
The bus ticket price from New York Penn Station to Chicago starts at $79. The best way to find cheap bus tickets from New York Penn Station to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the bus ride from New York Penn Station to Chicago?
The average travel time between New York Penn Station and Chicago is around , although the fastest bus will take about 18h 55m. This is the time it takes to travel the 712 miles that separates the two cities.
How many daily bus connections are there between New York Penn Station and Chicago?
The number of buses from New York Penn Station to Chicago can differ depending on the day of the week. On average, there are 29 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from New York Penn Station to Chicago by comparing and selecting the bus that fits you travel style and budget on Busbud.
Which bus companies travel from New York Penn Station to Chicago?
When taking the bus from New York Penn Station to Chicago, you can travel comfortably and safely with Amtrak, FlixBus.
What are the departure and arrival stations when taking the bus from New York Penn Station to Chicago?
Buses traveling between New York Penn Station and Chicago leave from 31st St & 8th Ave or Penn Station and arrive at Downtown Greyhound Station, Chicago O'Hare International Airport, Turimex California Ave.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
Where are the popular stations and stops in New York Penn Station and Chicago?
Stops in New York City
A - 31st St & 8th Ave
349 W 31st St (between 8th & 9th Avenue), New York, NY 10001
B - Penn Station
254 W 31st St, New York, NY 10001, USA
C - 34th St & 7th Ave
430 7th Avenue between 33rd and 34th Streets, NYC (Penn Station - In front of the Modell's Sports, across from the Pennsylvania Hotel, 1 block from the New Yorker Hotel)
