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

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There are 11 ways to get from Chicago to Times Square by 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. 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 14m
    $80–438

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    4h 36m
    $56–258

  3. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    20h 10m
    $95–250

  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
    $110–400

  5. Drive 790.4 mi

    1. Drive from Chicago to Times Squarecar car 790.4 mi
    13h 10m
    $145–209

  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)plane plane ORD - EWR
    4h 41m
    $72–333

  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)plane plane ORD - JFK
    4h 37m
    $816–1,024

  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 2m
    $217–671

  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 40m
    $94–463

  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 44m
    $104–1,105

  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 34m
    $108–241

Chicago to Times Square by bus (Flixbus)

Calendar7Weekly Buses
Duration20h 10mAverage Duration
Ticket$95Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA) every 3 hours. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown once daily. Tickets cost $95–250 and the journey takes 20h 10m.

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