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How to get fromChicago to Highlandsby plane, ferry, bus (Flixbus, Greyhound), train, car, subway, bus, bus (Greyhound), or train (Amtrak)

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There are 12 ways to get from Chicago to Highlands by plane, ferry, bus (Flixbus, Greyhound), train, car, subway, bus, bus (Greyhound), or train (Amtrak)

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, ferry

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the ferry from East 35th St., NYC to Highlands, NJferry ferry
    6h 49m
    $218–703

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train, line 4 subway, ferry

    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 subway from 125th Street to Wall Stsubway subway
    4. Take the ferry from Pier 11/Wall St., NYC to Highlands, NJferry ferry
    9h 5m
    $102–475

  3. 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 Port Authority Bus Terminal to Highlands, NJbus bus
    22h 48m
    $186–303

  4. Train, ferry

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    3. Take the ferry from Pier 11/Wall St., NYC to Highlands, NJferry ferry
    23h
    $534–844

  5. Drive  796.8 mi

    1. Drive from Chicago to Highlandscar car 796.8 mi
    13h 42m
    $146–211

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the ferry from East 35th St., NYC to Highlands, NJferry ferry
    7h 7m
    $148–543

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Airport Railroad Station to Red Banktrain train
    7h 17m
    $152–899

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the ferry from Pier 11/Wall St., NYC to Highlands, NJferry ferry
    7h 3m
    $334–907

  9. Fly Chicago O'Hare International Airport to Lehigh Valley International Airport, bus, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Lehigh Valley International Airport (ABE)plane plane ORD - ABE
    2. Take the bus from Lehigh Valley Intl Airport to Broadway At Cedarbus bus
    3. Take the ferry from Pier 11/Wall St., NYC to Highlands, NJferry ferry
    8h 44m
    $138–445

  10. Fly Chicago Midway International Airport to Philadelphia International Airport, train, ferry

    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
    3. Take the ferry from East 35th St., NYC to Highlands, NJferry ferry
    8h 30m
    $190–1,032

  11. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the bus from Port Authority Bus Terminal to Highlands, NJbus bus
    25h
    $214–332

  12. Train

    1. Take the train from Chicago Union Station to Newark Penn Stationtrain train Cardinal
    2. Take the train from Newark Penn Station to Red Banktrain train Njcl / ...
    30h 29m
    $629–984

Chicago to Highlands by bus

Calendar15Weekly Buses
Duration22h 48mAverage Duration
Ticket$186Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Highlands.ExpandLaunch map view
  • Distance: 769.9 mi
  • Duration: 6h 49m

What companies run services between Chicago, IL, USA and Highlands, NJ, USA?

You can take a bus from Chicago Bus Station to Highlands, NJ via Newark Penn Station and Port Authority Bus Terminal in around 22h 48m. Alternatively, you can take a train from Chicago Union Station to Bay Ave At Washington Ave# via Newark Penn Station, Red Bank, and Red Bank Rail Station in around 30h 29m.

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