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How to get fromChicago to Annandale-on-Hudsonby plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

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There are 7 ways to get from Chicago to Annandale-on-Hudson by plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

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 Albany County Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Rhinecliff Amtrak Stationtrain train
    6h 52m
    $198–973

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

    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 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    4. Take the bus from Poughkeepsie Train Station to Route 199 & Route 9Gbus bus
    10h 23m
    $128–552

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Rhinecliff Amtrak Stationtrain train Lake Shore Limited
    18h 38m
    $321–627

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from New York to Kingstonbus bus
    19h 56m
    $225–407

  5. Drive 825.1 mi

    1. Drive from Chicago to Annandale-on-Hudsoncar car 825.1 mi
    14h 5m
    $151–218

  6. Fly Chicago O'Hare International Airport to Albany County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Rhinecliff Amtrak Stationtrain train
    7h 19m
    $168–823

  7. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    8h 11m
    $226–593

Chicago Midway International Airport (MDW) to Albany County Airport (ALB) flights

Calendar31Weekly Planes
Duration2h 58mAverage Duration
Ticket$142Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Annandale-on-Hudson.ExpandLaunch map view
  • Distance: 796.8 mi
  • Duration: 6h 52m

What companies run services between Chicago, IL, USA and Annandale-on-Hudson, NY, USA?

Amtrak operates a train from Chicago Union Station to Rhinecliff Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h 25m. Alternatively, you can take a bus from Chicago Bus Station to Annandale-on-Hudson via Newark Penn Station, Port Authority Bus Terminal, New York, and Kingston in around 19h 56m.

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