Rome2Rio

How to get fromEastham to Chicagoby bus, plane, train, bus (Flixbus) or car

Find Transport to Chicago

See all options

There are 9 ways to get from Eastham to Chicago by bus, plane, train, bus (Flixbus), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    7h 56m
    $124–544

  2. Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus
    2. Take the train from Boston to Providencetrain
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    9h 56m
    $78–976

  3. Bus, train

    1. Take the bus from Hyannis Transportation Center to Boston South BusesbusHyannis - South Shore to Logan Airport
    2. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    26h 37m
    $181–764

  4. Bus

    1. Take the bus from Hyannis Transportation Center to Boston South Busesbus
    2. Take the bus from Boston to New York Midtownbus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus
    30h
    $156–329

  5. Drive 1,048.5 mi

    1. Drive from Eastham to Chicagocar1,048.5 mi
    18h 10m
    $192–277

  6. Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)planeBOS - ORD
    8h 13m
    $129–384

  7. Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus
    2. Take the train from Boston to Providencetrain
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    9h 25m
    $103–1,096

  8. Bus to Boston Logan Airport, fly to General Mitchell International Airport, train

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    10h 3m
    $297–789

  9. Bus, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus
    2. Take the bus from Boston to Boston Manchester Airportbus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    9h 35m
    $139–696

Eastham to Chicago by bus and train

Calendar7Weekly Services
Duration26h 37mAverage Duration
Ticket$181Cheapest Price
See schedules

Questions & Answers

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

You can take a bus from Eastham to Chicago Bus Station via Hyannis Transportation Center, Boston, Bus Terminal South Station, Boston, and New York Midtown in around 30h.

Transport is disrupted due to the Russia-Ukraine war. Read more

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Where to next?

Trips from Eastham

Trips to Chicago

Popular routes