Rome2Rio

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

Find Transport to Times Square

See all options

There are 11 ways to get from Chicago to Times Square by plane, train (Amtrak), bus (Greyhound), car, train, or bus (Flixbus)

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 Midway International Airport to Laguardia Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    4h 21m
    $136–708

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    4h 44m
    $76–324

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    20h 12m
    $290–600

  4. 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 39m
    $157–331

  5. Drive 790.4 mi

    1. Drive from Chicago to Times Squarecar car 790.4 mi
    13h 11m
    $145–209

  6. Fly Chicago O'Hare International Airport to Laguardia Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    4h 43m
    $86–348

  7. 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)plane plane ORD - EWR
    4h 42m
    $112–363

  8. 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
    $181–820

  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)plane plane ORD - HPN
    2. Take the train from White Plains to Grand Central Terminaltrain train
    6h 45m
    $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)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    5h 49m
    $176–1,408

  11. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2642 / ...
    22h 40m
    $140–230

Chicago to Times Square by train (Amtrak)

Calendar10Weekly Trains
Duration20h 12mAverage Duration
Ticket$290Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Times Square.ExpandLaunch map view
  • Distance: 742.8 mi
  • Duration: 4h 21m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station once daily. Tickets cost $290–600 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

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers