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How to get fromChicago to Winslowby plane, train, train (Amtrak), bus, taxi, car, or shuttle

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There are 9 ways to get from Chicago to Winslow by plane, train, train (Amtrak), bus, taxi, car, or shuttle

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 Flagstaff, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Flagstaff (FLG)plane plane ORD - FLG
    2. Take the train from Flagstaff to Winslow Stationtrain train
    9h 49m
    $164–612

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to Winslow Stationtrain train Southwest Chief
    30h 36m
    $500–1,100

  3. Bus, taxi

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus
    2. Take the bus from St Louis Bus Station to Holbrookbus bus
    3. Take the taxi from Holbrook to Winslowtaxi taxi
    33h 22m
    $306–533

  4. Drive 1,548.8 mi

    1. Drive from Chicago to Winslowcar car 1,548.8 mi
    26h 45m
    $283–409

  5. Fly Chicago O'Hare International Airport to Phoenix, shuttle, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Phoenix (PHX)plane plane ORD - PHX
    2. Take a shuttle bus from Sky Harbor International Airport to Flagstaff Amtrakshuttle bus
    3. Take the train from Flagstaff to Winslow Stationtrain train
    10h 19m
    $404–599

  6. Fly Chicago Midway International Airport to Phoenix, shuttle, train

    1. Fly from Chicago Midway International Airport (MDW) to Phoenix (PHX)plane plane MDW - PHX
    2. Take a shuttle bus from Sky Harbor International Airport to Flagstaff Amtrakshuttle bus
    3. Take the train from Flagstaff to Winslow Stationtrain train
    10h 9m
    $324–459

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

    1. Fly from Chicago Midway International Airport (MDW) to Albuquerque International Airport (ABQ)plane plane MDW - ABQ
    2. Take the train from Albuquerque Alvarado Transportation Center to Winslow Stationtrain train
    10h 56m
    $262–996

  8. Fly Chicago O'Hare International Airport to Albuquerque International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Albuquerque International Airport (ABQ)plane plane ORD - ABQ
    2. Take the train from Albuquerque Alvarado Transportation Center to Winslow Stationtrain train
    11h 19m
    $222–846

  9. Fly Chicago Midway International Airport to Flagstaff, train

    1. Fly from Chicago Midway International Airport (MDW) to Flagstaff (FLG)plane plane MDW - FLG
    2. Take the train from Flagstaff to Winslow Stationtrain train
    9h 37m
    $194–762

Chicago to Winslow by train (Amtrak)

Calendar7Weekly Trains
Duration30h 36mAverage Duration
Ticket$500Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winslow.ExpandLaunch map view
  • Distance: 1,444.5 mi
  • Duration: 9h 49m

What companies run services between Chicago, IL, USA and Winslow, AZ, USA?

Amtrak operates a train from Chicago Union Station to Winslow Station once daily. Tickets cost $500–1,100 and the journey takes 30h 36m.

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