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Winter Park to Chicago buses

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Trip Overview

The average bus between Winter Park and Chicago takes 28h 48m and the fastest bus takes 25h 27m. The bus service runs several times per day from Winter Park 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.

28h 48m
Duration
1,163 mi
Distance
$242
Average price
4 times a day
Frequency

Bus

best
  1. Take the bus from Orlando Bus Station to Atlanta Bus Stationbus bus FlixBus N2401 / ...
  2. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus Greyhound US0100
26h 8m
$177–322

Winter Park to Chicago bus times

Buses run 4 times a day between Winter Park and Chicago. The earliest departure is at 7:36 AM in the morning, and the last departure from Winter Park is at 11:16 PM which arrives into Chicago at 8:25 AM. All services require a transfer at N Garland Ave & W Amelia St and take an average of 28h 48m. The schedules shown below are for the next available departures.

Departing Thursday, October 29, 2026

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    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA34h 8m • 3 changes

Departing Friday, October 30, 2026

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 54m • 3 changes

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA26h 42m • 3 changes

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA25h 51m • 3 changes

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    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA27h 53m • 3 changes
  • Show more

Departing Saturday, October 31, 2026

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 25m • 3 changes

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA26h 45m • 3 changes

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA25h 49m • 3 changes

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    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 53m • 3 changes

Departing Sunday, November 1, 2026

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 42m • 3 changes

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA26h 28m • 3 changes

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA25h 27m • 3 changes

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    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 29m • 3 changes
  • Show more

Departing Monday, November 2, 2026

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    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 54m • 3 changes

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA26h 42m • 3 changes

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA25h 51m • 3 changes

  •  → 

    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA27h 53m • 3 changes
  • Show more

Departing Tuesday, November 3, 2026

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 54m • 3 changes

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA26h 42m • 3 changes

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA25h 51m • 3 changes

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    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA34h 8m • 3 changes

Departing Wednesday, November 4, 2026

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAFlixbus USA28h 54m • 3 changes

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA26h 42m • 3 changes

  •  → 

    Arrives next day

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA25h 51m • 3 changes

  •  → 

    Arrives +2 days

    Lynx Central Florida TransportLynx Central Florida TransportFlixbus USAGreyhound USA34h 8m • 3 changes

Frequently asked questions

Want to know about travelling from Winter Park 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 Winter Park to Chicago.ExpandLaunch map view
  • Distance: 1,162.8 mi
  • Duration: 28h 48m

What companies run services between Winter Park, FL, USA and Chicago, IL, USA?

You can take a bus from W Morse Blvd & S New York Ave to Chicago Bus Station via N Garland Ave & W Amelia St, N John Young Pkwy & Business Center Blvd, Orlando Bus Station, and Atlanta Bus Station in around 26h 8m.

Operators