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How to get fromChicago to Brewsterby plane, bus, train (Amtrak), bus (Flixbus), car, or train

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There are 11 ways to get from Chicago to Brewster by plane, bus, train (Amtrak), bus (Flixbus), car, or train

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 Boston Logan Airport, bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the bus from Logan International Airport to Hyannis Transportation Centerbus bus
    10h 17m
    $636–1,051

  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    3. Take the bus from Boston South Station to Hyannis Transportation Centerbus bus
    12h 49m
    $92–367

  3. Train

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the train from South Station to Hyannistrain train CapeFLYER
    25h 53m
    $379–754

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Bostonbus bus
    3. Take the bus from Boston to Hyannisbus bus
    27h 50m
    $193–339

  5. Drive 1,038.3 mi

    1. Drive from Chicago to Brewstercar car 1,038.3 mi
    18h 9m
    $190–274

  6. Fly Chicago Midway International Airport to Boston Logan Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the bus from Logan International Airport to Hyannis Transportation Centerbus bus
    9h 59m
    $136–551

  7. Fly Chicago Midway International Airport to Provincetown Municipal Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC)plane plane MDW - PVC
    2. Take the bus from MacMillan Pier, Provincetown to Brewster Senior Housing/COAbus bus
    9h 9m
    $128–611

  8. Fly Chicago Midway International Airport to Manchester Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the bus from Boston to Hyannisbus bus
    12h 8m
    $130–616

  9. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, bus

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    3. Take the bus from Boston South Station to Hyannis Transportation Centerbus bus
    12h 19m
    $108–437

  10. Fly Chicago Midway International Airport to Bradley International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Hartford Union Station to Bostonbus bus
    3. Take the bus from Boston to Hyannisbus bus
    12h 42m
    $140–584

  11. Fly Chicago O'Hare International Airport to Bradley International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Hartford Union Station to Bostonbus bus
    3. Take the bus from Boston to Hyannisbus bus
    13h 13m
    $114–484

Chicago to Brewster by bus

Calendar32Weekly Buses
Duration27h 50mAverage Duration
Ticket$193Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Brewster.ExpandLaunch map view
  • Distance: 989.6 mi
  • Duration: 10h 17m

What companies run services between Chicago, IL, USA and Brewster, MA, USA?

You can take a train from Chicago Union Station to Brewster via Boston, South Station, and Hyannis in around 25h 53m. Alternatively, you can take a bus from Chicago Bus Station to Brewster Senior Housing/COA via New York Midtown, Boston, Hyannis, Hyannis Transportation Center, and Star Market, Harwich Port in around 27h 50m.

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