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

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There are 11 ways to get from Chicago to Bristol by plane, bus, train, bus (Greyhound, Amtrak), car, or bus (Flixbus, 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 Portland, Amtrak Thruway

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the bus from Portland, ME to Damariscotta, MEbus bus
    7h 53m
    $158–684

  2. Fly Chicago O'Hare International Airport to Portland, Amtrak Thruway

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the bus from Portland, ME to Damariscotta, MEbus bus
    8h 19m
    $134–554

  3. Train, Amtrak Thruway

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from South Station to Damariscotta, MEbus bus Boston
    26h 41m
    $379–740

  4. Bus, Amtrak Thruway via Brook Park

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Bostonbus bus
    3. Take the bus from South Station to Damariscotta, MEbus bus
    26h 44m
    $203–370

  5. Drive 1,092.1 mi

    1. Drive from Chicago to Bristolcar car 1,092.1 mi
    20h 30m
    $200–288

  6. Fly Chicago O'Hare International Airport to Bangor, Amtrak Thruway

    1. Fly from Chicago O'Hare International Airport (ORD) to Bangor (BGR)plane plane ORD - BGR
    2. Take the bus from Bangor, ME to Damariscotta, MEbus bus
    9h 2m
    $164–678

  7. 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 Boston Logan Airport Terminal C to Damariscotta, MEbus bus
    9h 8m
    $158–581

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

    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 South Station to Damariscotta, MEbus bus
    10h 48m
    $160–641

  9. Fly Chicago O'Hare International Airport to Manchester Airport, bus, Amtrak Thruway

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the bus from South Station to Damariscotta, MEbus bus
    11h 22m
    $146–511

  10. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, Amtrak Thruway

    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 South Station to Damariscotta, MEbus bus
    11h 4m
    $138–462

  11. Bus, Amtrak Thruway

    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 South Station to Damariscotta, MEbus bus
    26h 57m
    $225–369

Chicago Midway International Airport (MDW) to Portland (PWM) flights

Calendar19Weekly Planes
Duration3h 56mAverage Duration
Ticket$123Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Bristol.ExpandLaunch map view
  • Distance: 970.4 mi
  • Duration: 7h 53m

What companies run services between Chicago, IL, USA and Bristol, ME, USA?

You can take a bus from Chicago Bus Station to Bristol via Cleveland Bus Station, Boston, South Station, and Damariscotta, ME in around 26h 44m.

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