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How to get fromChicago Union Station to Times Squareby subway, plane, bus (Flixbus), train (Amtrak), car, train, or bus (Greyhound)

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There are 11 ways to get from Chicago Union Station to Times Square by subway, plane, bus (Flixbus), train (Amtrak), car, train, 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.

  1. Subway to Chicago Midway International Airport, fly to Laguardia Airport, line 7 subway

    best
    1. Take the subway from Quincy to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the subway from 74 St-Broadway to 42 St-Times Squaresubway subway
    4h 37m
    $186–558

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Grand Central Terminaltrain train
    6h 57m
    $114–523

  3. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    17h 14m
    $140–240

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    20h 12m
    $310–650

  5. Drive 791.3 mi

    1. Drive from Chicago Union Station to Times Squarecar car 791.3 mi
    13h 11m
    $145–209

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, line 7 subway

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the subway from 74 St-Broadway to 42 St-Times Squaresubway subway
    4h 56m
    $216–658

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Airport Railroad Station to New York Penn Stationtrain train
    4h 54m
    $182–883

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    4h 53m
    $326–874

  9. Train to General Mitchell International Airport, fly to Laguardia Airport

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Laguardia Airport (LGA)plane plane MKE - LGA
    6h 5m
    $183–822

  10. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    6h 4m
    $166–1,008

  11. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus Greyhound US0164
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus Greyhound US0670 / ...
    21h 48m
    $170–361

Chicago Union Station to Times Square by foot and bus (Flixbus)

Calendar16Weekly Services
Duration17h 14mAverage Duration
Ticket$140Cheapest Price
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Questions & Answers

Map of how to get from Chicago Union Station to Times Square.ExpandLaunch map view
  • Distance: 744.6 mi
  • Duration: 4h 37m

What companies run services between Chicago Union Station, IL, USA and Times Square, NY, USA?

Flixbus USA operates a bus from Chicago Bus Station to New York Midtown twice daily. Tickets cost $140–240 and the journey takes 17h 5m. Alternatively, Amtrak operates a train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station once daily. Tickets cost $310–650 and the journey takes 20h 12m.

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