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How to get fromChicago to Winter Parkby plane, bus, train (Amtrak), bus (Greyhound), car, taxi, or shuttle

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There are 9 ways to get from Chicago to Winter Park by plane, bus, train (Amtrak), bus (Greyhound), car, taxi, 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 Midway International Airport to Denver, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Denver (DEN)plane plane MDW - DEN
    2. Take the bus from Denver International Airport to Winter Park, CObus bus
    7h 13m
    $212–274

  2. Fly Chicago O'Hare International Airport to Yampa Valley Airport, shuttle, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Yampa Valley Airport (HDN)plane plane ORD - HDN
    2. Take a shuttle bus from Steamboat Springs, CO to Silverthorne, COshuttle bus
    3. Drive from Silverthorne, CO to Winter Parkcar car
    9h 52m
    $170–530

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Winter Park/Frasertrain train California Zephyr
    22h 53m
    $344–718

  4. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus Greyhound US0123S
    2. Take the bus from Denver International Airport to Winter Park, CObus bus From Airport
    25h 20m
    $242–377

  5. Drive 1,063.1 mi

    1. Drive from Chicago to Winter Parkcar car 1,063.1 mi
    17h 8m
    $194–281

  6. Fly Chicago O'Hare International Airport to Denver, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Denver (DEN)plane plane ORD - DEN
    2. Take the bus from Denver International Airport to Winter Park, CObus bus
    7h 34m
    $262–534

  7. Fly Chicago Midway International Airport to Colorado Springs Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Colorado Springs Airport (COS)plane plane MDW - COS
    2. Take the bus from Colorado Springs Airport to Denver International Airportbus bus
    3. Take the bus from Denver International Airport to Winter Park, CObus bus
    10h 3m
    $222–694

  8. Fly Chicago O'Hare International Airport to Colorado Springs Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Colorado Springs Airport (COS)plane plane ORD - COS
    2. Take the bus from Colorado Springs Airport to Denver International Airportbus bus
    3. Take the bus from Denver International Airport to Winter Park, CObus bus
    10h 37m
    $202–554

  9. Fly Chicago O'Hare International Airport to Aspen–Pitkin County Airport, bus, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Aspen–Pitkin County Airport (ASE)plane plane ORD - ASE
    2. Take the bus from AABC Airport DV to West Glenwood Park & Ridebus bus
    3. Take the bus from West Glenwood Park & Ride to Idaho Springsbus bus
    4. Take the taxi from Idaho Springs to Winter Parktaxi taxi
    10h 53m
    $266–648

Chicago to Winter Park by train and bus (Amtrak)

Calendar7Weekly Services
Duration22h 53mAverage Duration
Ticket$344Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winter Park.ExpandLaunch map view
  • Distance: 994.3 mi
  • Duration: 7h 13m

What companies run services between Chicago, IL, USA and Winter Park, CO, USA?

Amtrak operates a train from Chicago Union Station to Winter Park/Fraser once daily. Tickets cost $340–750 and the journey takes 21h 48m. Alternatively, you can take a bus from Chicago Bus Station to Winter Park, CO via Denver Union Station, Union Station, Denver Airport Station, and Denver International Airport in around 25h 20m.

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