Rome2Rio

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

Find Transport to Westerly

See all options

There are 13 ways to get from Chicago to Westerly by plane, train, train (Amtrak), bus, car, or bus (Flixbus)

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 Theodore Francis Green State Airport, train

    best
    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 Providence to Westerly Amtrak Stationtrain train
    6h 33m
    $66–517

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the train from Boston to Westerly Amtrak Stationtrain train Northeast Regional
    24h 3m
    $103–796

  3. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to New Haven Union Stationbus bus
    4. Take the train from New Haven to Westerly Amtrak Stationtrain train
    26h 39m
    $127–501

  4. Drive 918.9 mi

    1. Drive from Chicago to Westerlycar car 918.9 mi
    15h 39m
    $168–243

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

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to Westerly Amtrak Stationtrain train
    6h 13m
    $86–627

  6. Fly Chicago O'Hare International Airport to Boston Logan Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the train from Boston to Westerly Amtrak Stationtrain train
    6h 49m
    $134–644

  7. Fly Chicago Midway International Airport to Boston Logan Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Boston to Westerly Amtrak Stationtrain train
    6h 25m
    $134–844

  8. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Westerly Amtrak Stationtrain train
    8h 9m
    $100–701

  9. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Westerly Amtrak Stationtrain train
    8h 31m
    $76–521

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

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to Westerly Amtrak Stationtrain train
    8h 4m
    $128–1,038

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to Westerly Amtrak Stationtrain train
    8h 42m
    $408–1,138

  12. Train via New York (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Westerly Amtrak Stationtrain train Northeast Regional
    24h 5m
    $137–655

  13. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Providencebus bus
    3. Take the bus from Turks Head to Westerly Railroad Stationbus bus 95x
    27h 11m
    $129–320

Chicago to Westerly by train (Amtrak)

Calendar7Weekly Trains
Duration24h 3mAverage Duration
Ticket$103Cheapest Price
See schedules

Questions & Answers

What companies run services between Chicago, IL, USA and Westerly, RI, USA?

You can take a train from Chicago Union Station to Westerly Amtrak Station via Boston in around 24h 3m. Alternatively, you can take a bus from Chicago Bus Station to Westerly Railroad Station via New York Midtown, Providence, and Turks Head in around 27h 11m.

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

Trips from Chicago

Trips to Westerly

Popular routes