Rome2Rio

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

Find Transport to Winsted

See all options

There are 6 ways to get from Chicago to Winsted by plane, bus, train, bus (Flixbus, Greyhound), car, or bus (Greyhound)

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 from Chicago Midway International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)planeMDW - BDL
    2. Take the bus from Central Row @ Main St to Park Pl @ NW CT Comm Collegebus
    6h 24m
    $104–564

  2. Train, bus

    1. Take the train from Chicago Union Station to Springfieldtrain
    2. Take the train from Springfield to Hartford Amtrak Stationtrain
    3. Take the bus from Asylum St @ Union Pl to Park Pl @ NW CT Comm Collegebus926
    22h 50m
    $141–682

  3. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus
    2. Take the bus from Newark Penn Station to Hartford Union Stationbus
    3. Take the bus from Asylum St @ Union Pl to Park Pl @ NW CT Comm Collegebus926
    25h 29m
    $139–332

  4. Drive 865.4 mi

    1. Drive from Chicago to Winstedcar865.4 mi
    14h 46m
    $158–229

  5. Fly from Chicago O'Hare International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)planeORD - BDL
    2. Take the bus from Central Row @ Main St to Park Pl @ NW CT Comm Collegebus
    6h 56m
    $354–664

  6. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus
    3. Take the bus from Port Authority Bus Terminal to Hartford Union Stationbus
    4. Take the bus from Asylum St @ Union Pl to Park Pl @ NW CT Comm Collegebus926
    27h 38m
    $135–361

Chicago to Winsted by train and bus

Calendar7Weekly Services
Duration22h 50mAverage Duration
Ticket$141Cheapest Price
See schedules

Questions & Answers

What companies run services between Chicago, IL, USA and Winsted, CT, USA?

You can take a bus from Chicago Bus Station to Park Pl @ NW CT Comm College via Newark Penn Station, Hartford, Union Station, and Asylum St @ Union Pl in around 25h 29m.

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

More Questions & Answers

Trips from Chicago

Trips to Winsted

Popular routes