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Chicago to Pawling buses

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Trip Overview

The average bus between Chicago and Pawling takes 47h 51m and the fastest bus takes 46h 9m. The bus runs, on average, 4 times per week from Chicago to Pawling. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

47h 51m
Duration
1,095 mi
Distance
$205
Average price
4 times a week
Frequency

Chicago to Pawling bus times

Buses run 4 times a week between Chicago and Pawling. The earliest departure is at 12:25 PM in the afternoon, and the last departure from Chicago is at 7:15 PM which arrives into Pawling at 6:24 PM. All services require a transfer at New York Midtown and take an average of 47h 51m. The schedules shown below are for the next available departures.

Departing Tuesday, November 10, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USALeprechaun LinesDutchess County Public Transit2d 4h • 3 changes

Departing Wednesday, November 11, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USALeprechaun LinesDutchess County Public Transit46h 9m • 3 changes

Departing Saturday, November 14, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USALeprechaun LinesDutchess County Public Transit46h 9m • 3 changes

Frequently asked questions

Want to know about travelling from Chicago to Pawling? 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 Pawling.ExpandLaunch map view
  • Distance: 1,094.8 mi
  • Duration: 47h 51m

What companies run services between Chicago, IL, USA and Pawling, NY, USA?

You can take a bus from Chicago Bus Station to Chamber of Commerce via New York Midtown, White Plains Bus Station, TransCenter, and Poughkeepsie Train Station in around 27h 1m.

Operators