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Wakefield to Chicago trains

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Trip Overview

The average train between Wakefield and Chicago takes 25h 25m and the fastest train takes 23h 4m. The train runs, on average, 6 times per week from Wakefield 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.

25h 25m
Duration
1,025 mi
Distance
$658
Average price
6 times a week
Frequency

Wakefield to Chicago train times

Trains run 6 times a week between Wakefield and Chicago. The earliest departure is at 12:08 PM in the afternoon, and the last departure from Wakefield is at 9:58 PM which arrives into Chicago at 10:12 AM. All services require a transfer at Oak Grove and take an average of 25h 25m. The schedules shown below are for the next available departures.

Departing Monday, November 9, 2026

  •  → 

    Arrives next day

    MBTAMBTAAmtrak23h 4m • 2 changes

Departing Tuesday, November 10, 2026

  •  → 

    Arrives next day

    MBTAMBTAAmtrak23h 4m • 2 changes

Departing Wednesday, November 11, 2026

  •  → 

    Arrives next day

    MBTAMBTAAmtrak23h 4m • 2 changes

Departing Thursday, November 12, 2026

  •  → 

    Arrives next day

    MBTAMBTAAmtrak23h 4m • 2 changes

Departing Friday, November 13, 2026

  •  → 

    Arrives next day

    MBTAMBTAAmtrak23h 4m • 2 changes
  •  → 

    Arrives +2 days

    MBTAMBTAAmtrak37h 14m • 2 changes

Frequently asked questions

Want to know about travelling from Wakefield 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 Wakefield to Chicago.ExpandLaunch map view
  • Distance: 1,025.3 mi
  • Duration: 25h 25m

What companies run services between Wakefield, MA, USA and Chicago, IL, USA?

Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $550–900 and the journey takes 22h 15m.

Operators