Rome2Rio

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

Find Transport to Times Square

See all options

There are 12 ways to get from Chicago to Times Square by plane, subway, 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. Fly Chicago O'Hare International Airport to Laguardia Airport, subway

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)planeORD - LGA
    2. Take the subway from Jackson Hts-Roosevelt Av to 42 St-Bryant Parksubway
    4h 31m
    $60–268

  2. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    20h 10m
    $100–270

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn StationtrainLake Shore Limited / ...
    20h 12m
    $130–480

  4. Drive 790.4 mi

    1. Drive from Chicago to Times Squarecar790.4 mi
    13h 3m
    $145–209

  5. Fly Chicago Midway International Airport to Laguardia Airport

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)planeMDW - LGA
    4h 14m
    $76–378

  6. Fly Chicago O'Hare International Airport to Newark Liberty International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)planeORD - EWR
    4h 42m
    $82–313

  7. 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)planeORD - JFK
    4h 37m
    $816–1,024

  8. Fly Chicago Midway International Airport to Newark Liberty International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Newark Liberty International Airport (EWR)planeMDW - EWR
    4h 18m
    $88–373

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)planeORD - HPN
    2. Take the train from White Plains to Grand Central Terminaltrain
    6h 41m
    $104–493

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

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)planeMDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain
    5h 44m
    $94–1,045

  11. Fly Chicago O'Hare International Airport to Philadelphia International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Philadelphia International Airport (PHL)planeORD - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain
    6h 10m
    $114–935

  12. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus StationbusGreyhound US0164
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus TerminalbusGreyhound US0670 / ...
    21h 34m
    $111–277

Chicago to Times Square by bus (Flixbus)

Calendar7Weekly Buses
Duration20h 10mAverage Duration
Ticket$100Cheapest Price
See schedules

Questions & Answers

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

Flixbus USA operates a bus from Chicago Bus Station to New York Midtown once daily. Tickets cost $100–270 and the journey takes 20h 10m. Alternatively, Amtrak operates a train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station once daily. Tickets cost $130–480 and the journey takes 20h 12m.

Airlines
Train operators
Bus operators

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

More Questions & Answers

Where to next?

Trips from Chicago

Trips to Times Square

Popular routes