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How to get fromTimes Square to Chicagoby bus, plane, train (Amtrak), bus (Flixbus), car, subway, train or bus (Greyhound)

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There are 10 ways to get from Times Square to Chicago by bus, plane, train (Amtrak), bus (Flixbus), car, subway, 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. Bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Port Authority Bus Terminal to Terminal Bbus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    5h 3m

  2. Subway, bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the subway from 42 St-Port Authority Bus Terminal to 125 Stsubway
    2. Take the bus from W 125 St/Saint Nicholas Av to Laguardia Rd/94 Stbus
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    5h 20m
    $62–275

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union StationtrainLake Shore Limited / ...
    19h 32m
    $120–550

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    20h 25m
    $95–230

  5. Drive 790 mi

    1. Drive from Times Square to Chicagocar790 mi
    13h 1m
    $145–209

  6. Fly Laguardia Airport to Chicago Midway International Airport

    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    5h 9m
    $87–435

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

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    5h 8m
    $816–1,023

  8. Bus to Newark Liberty International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Port Authority Bus Terminal to Terminal Bbus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW)planeEWR - MDW
    4h 52m

  9. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Grand Central Terminal to White Plainstrain
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    6h 59m
    $80–383

  10. Bus via Baltimore

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus StationbusGreyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus StationbusGreyhound US0164
    22h 55m
    $113–321

Times Square to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration19h 32mAverage Duration
Ticket$120Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $120–550 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $95–230 and the journey takes 20h 25m.

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