There are 12 ways to get from Chicago Union Station to Times Square by subway, plane, train (Amtrak), bus (Flixbus), car, train, bus, 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.
Subway to Chicago Midway International Airport, fly to Laguardia Airport, subway
best- Take the subway from Quincy to Midwaysubway
- Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane MDW - LGA
- Take the subway from Jackson Hts-Roosevelt Av to 42 St-Bryant Parksubway
4h 32m$206–658Fly Chicago O'Hare International Airport to Westchester County Airport, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane ORD - HPN
- Take the train from White Plains to Grand Central Terminaltrain
6h 55m$100–473Train (Amtrak)
- Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain Lake Shore Limited / ...
20h 12m$240–550Bus (Flixbus)
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2640 / ...
20h 19m$140–220Drive 791.3 mi
- Drive from Chicago Union Station to Times Squarecar 791.3 mi
13h 12m$145–209Fly Chicago O'Hare International Airport to Laguardia Airport, subway
- Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane ORD - LGA
- Take the subway from Jackson Hts-Roosevelt Av to 42 St-Bryant Parksubway
4h 45m$136–558Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane ORD - EWR
- Take the train from Newark Airport Railroad Station to New York Penn Stationtrain
4h 53m$144–883Fly Chicago O'Hare International Airport to John F. Kennedy International Airport
- Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane ORD - JFK
4h 56m$326–874Train to General Mitchell International Airport, fly to Laguardia Airport
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Laguardia Airport (LGA)plane MKE - LGA
5h 57m$167–865Fly Chicago Midway International Airport to Philadelphia International Airport, train
- Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane MDW - PHL
- Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain
5h 59m$164–979Fly Chicago O'Hare International Airport to Lehigh Valley International Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Lehigh Valley International Airport (ABE)plane ORD - ABE
- Take the bus from Lehigh Valley Intl Airport to New York, NYbus
7h 10m$128–420Bus via Baltimore
- Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus Greyhound US0164
- Take the bus from Baltimore to New Yorkbus Ppb 8724 / ...
22h 31m$164–272
Chicago Union Station to Times Square by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chicago Union Station to Times Square is to bus which costs $140 - $220 and takes 20h 19m.
The fastest way to get from Chicago Union Station to Times Square is to subway and fly which takes 4h 32m and costs $200 - $700.
Yes, there is a direct bus departing from Chicago Bus Station station and arriving at New York Midtown. Services depart twice daily, and operate every day. The journey takes approximately 20h 10m.
Yes, there is a direct train departing from Chicago Union Station station and arriving at Ny Moynihan Train Hall At Penn Station station. Services depart once daily, and operate every day. The journey takes approximately 20h 12m.
The distance between Chicago Union Station and Times Square is 749 miles. The road distance is 795.9 miles.
The best way to get from Chicago Union Station to Times Square without a car is to train which takes 20h 12m and costs $240 - $550.
It takes approximately 4h 32m to get from Chicago Union Station to Times Square, including transfers.
Chicago Union Station to Times Square bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago Union Station to Times Square train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago Union Station to Times Square is to train which takes 20h 12m and costs $240 - $550. Alternatively, you can bus, which costs $140 - $220 and takes 20h 19m, you could also fly, which costs $320 - $900 and takes 4h 56m.
What companies run services between Chicago Union Station, IL, USA and Times Square, NY, USA?
Amtrak operates a train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station once daily. Tickets cost $240–550 and the journey takes 20h 12m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown twice daily. Tickets cost $140–220 and the journey takes 20h 10m.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 14m
- When
- Every day
- Estimated price
- $95–500
Flights from Chicago O'Hare International Airport to Newark Liberty International Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $55–300
Flights from Chicago O'Hare International Airport to John F. Kennedy International Airport
- Ave. Duration
- 2h 27m
- When
- Every day
- Estimated price
- $55–300
Flights from General Mitchell International Airport to Laguardia Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 25m
- When
- Every day
- Estimated price
- $150–850
Flights from Chicago O'Hare International Airport to Westchester County Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $85–450
Flights from Chicago O'Hare International Airport to Westchester County Airport via Reagan Washington
- Ave. Duration
- 4h 35m
- When
- Every day
- Estimated price
- $90–470
Flights from Chicago O'Hare International Airport to Lehigh Valley International Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $60–340
- Phone
- +1 888-968-7282
- Website
- Chicago Transit Authority
Subway from Quincy to Midway
- Ave. Duration
- 31 min
- Frequency
- Every 15 minutes
- Estimated price
- $2–5
- Website
- Chicago Transit Authority
- Schedules at
- Chicago Transit Authority Schedules & Routes
- Adult
- $2–5
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Twice daily
- Estimated price
- $140–220
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
Chicago Union Station to Times Square bus services, operated by Flixbus USA, arrive at New York Midtown station.
Times Square is 1h ahead of Chicago Union Station. It is currently 3:10 PM in Chicago Union Station and 4:10 PM in Times Square.
Chicago Union Station to Times Square train services, operated by Amtrak, arrive at Ny Moynihan Train Hall At Penn Station.
Yes, the driving distance between Chicago Union Station to Times Square is 796 miles. It takes approximately 13h 12m to drive from Chicago Union Station to Times Square.
Book your Chicago Union Station to Times Square train tickets online with Omio.
Book your Chicago Union Station to Times Square bus tickets online with Omio and FlixBus.
There are 3695+ hotels available in Times Square.