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Chicago to Waterbury buses

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Trip Overview

The bus between Chicago and Waterbury takes 36h 29m. The bus runs, on average, 4 times per week from Chicago to Waterbury. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

36h 29m
Duration
1,044 mi
Distance
$223
Average price
4 times a week
Frequency

Chicago to Waterbury bus times

Buses run 4 times a week between Chicago and Waterbury. The service departs Chicago at 6:00 PM in the evening, which arrives into Waterbury at 07:29:21. All services require a transfer at Cleveland Bus Station and take an average of 36h 29m. The schedules shown below are for the next available departures.

Departing Wednesday, November 11, 2026

  •  → 

    Arrives +2 days

    Greyhound USAGreyhound USAVermont TranslinesGreen Mountain Transit36h 29m • 3 changes

Departing Saturday, November 14, 2026

  •  → 

    Arrives +2 days

    Greyhound USAGreyhound USAVermont TranslinesGreen Mountain Transit36h 29m • 3 changes

Departing Sunday, November 15, 2026

  •  → 

    Arrives +2 days

    Greyhound USAGreyhound USAVermont TranslinesGreen Mountain Transit36h 29m • 3 changes

Frequently asked questions

Want to know about travelling from Chicago to Waterbury? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Chicago to Waterbury.ExpandLaunch map view
  • Distance: 1,044 mi
  • Duration: 36h 29m

What companies run services between Chicago, IL, USA and Waterbury, VT, USA?

You can take a bus from Chicago Bus Station to Waterbury Main Street Opposite Park Row via Cleveland Bus Station, Greyhound \ Trailways Terminal, and Downtown Transit Center - Spot O in around 25h 56m.

Operators