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Middletown to Chicago buses

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Trip Overview

The average bus between Middletown and Chicago takes 33h 51m and the fastest bus takes 26h 2m. There is at least one bus per day from Middletown to Chicago. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

33h 51m
Duration
1,125 mi
Distance
$216
Average price
Once daily
Frequency

Middletown to Chicago bus times

Buses run once daily between Middletown and Chicago. The earliest departure is at 12:22 PM in the afternoon, and the last departure from Middletown is at 7:28 PM which arrives into Chicago at 6:10 AM. All services require a transfer at Central Row @ Main St and take an average of 33h 51m. The schedules shown below are for the next available departures.

Departing Monday, November 9, 2026

  •  → 

    Arrives next day

    CT TransitCT TransitFlixbus USAFlixbus USA26h 2m • 3 changes
  •  → 

    Arrives +3 days

    CT TransitCT TransitFlixbus USAFlixbus USA2d 11h • 3 changes

Departing Wednesday, November 11, 2026

  •  → 

    Arrives next day

    CT TransitCT TransitFlixbus USAFlixbus USA26h 2m • 3 changes
  •  → 

    Arrives +2 days

    CT TransitCT TransitFlixbus USAFlixbus USA35h 41m • 3 changes

Departing Thursday, November 12, 2026

  •  → 

    Arrives next day

    CT TransitCT TransitFlixbus USAFlixbus USA26h 2m • 3 changes
  •  → 

    Arrives +2 days

    CT TransitCT TransitFlixbus USAFlixbus USA35h 41m • 3 changes

Departing Friday, November 13, 2026

  •  → 

    Arrives next day

    CT TransitCT TransitFlixbus USAFlixbus USA26h 2m • 3 changes
  •  → 

    Arrives +2 days

    CT TransitCT TransitFlixbus USAFlixbus USA35h 41m • 3 changes

Frequently asked questions

Want to know about travelling from Middletown to Chicago? 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 Middletown to Chicago.ExpandLaunch map view
  • Distance: 1,124.8 mi
  • Duration: 33h 51m

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

You can take a bus from Main St @ Ferry St to Chicago Bus Station via Central Row @ Main St, Hartford Union Station, and New York Midtown in around 25h 56m.

Operators