Rome2Rio

Annapolis to Chicago buses

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Trip Overview

The bus between Annapolis and Chicago takes 18h. There is at least one bus per day from Annapolis 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.

18h
Duration
742 mi
Distance
$156
Average price
Once daily
Frequency

Annapolis to Chicago bus times

Buses run once daily between Annapolis and Chicago. The service departs Annapolis at 5:00 PM in the evening, which arrives into Chicago at 10:00:00. All services require a transfer, and take on average 18h. The schedules shown below are for the next available departures.

Departing Tuesday, November 10, 2026

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    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Departing Wednesday, November 11, 2026

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    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Departing Thursday, November 12, 2026

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    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Departing Friday, November 13, 2026

  •  → 

    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Departing Saturday, November 14, 2026

  •  → 

    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Departing Sunday, November 15, 2026

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    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Departing Monday, November 16, 2026

  •  → 

    Arrives next day

    Flixbus USAGreyhound USA18h • 1 change

Frequently asked questions

Want to know about travelling from Annapolis 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 Annapolis to Chicago.ExpandLaunch map view
  • Distance: 742.2 mi
  • Duration: 18h

What companies run services between Annapolis, MD, USA and Chicago, IL, USA?

You can take a bus from Annapolis to Chicago Bus Station via Washington Union Station in around 18h 55m.

Operators