- Must visit
The Charles Hosmer Morse Museum of American Art
Museum housing the world's most comprehensive collection of Louis Comfort Tiffany works, including lamps, windows, and chapel interiors.
Cheapest price on Sep 30
€192
Average ticket price on Sep 30
€192
Fastest journey on Sep 30
1 d 6 h
Average journey duration on Sep 30
1 d 6 h
Buses on Sep 30
1
Distance
1580 km
The best way to find a cheap bus ticket from Chicago, IL to Winter Park, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Winter Park, FL will cost around €192 if you buy it on the day, but the cheapest tickets can be found for only €192.
On Wed, Sep 30, we found 1 buses from Chicago, IL to Winter Park, FL, including 1 direct services.
On Wed, Sep 30 the direct buses cover the 1580 km distance in an average of 1 d 6 h but if you time it right, some buses will get you there in just 1 d 6 h .
On Wed, Sep 30 the slowest buses will take 1 d 6 h and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.


| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator FlixBus | Departure Time 12:00AM | Arrival Time 04:59AM | Duration 28h59 | Departure days Fri | Cheapest price €189 |
Operator Greyhound | Departure Time 03:50AM | Arrival Time 09:50AM | Duration 30h00 | Departure days Wed | Cheapest price €192 |
Operator Greyhound USA | Departure Time 06:10AM | Arrival Time 09:02AM | Duration 26h52 | Departure days Fri, Sat, Sun | Cheapest price €225 |
Operator Greyhound | Departure Time 11:10AM | Arrival Time 06:55PM | Duration 31h45 | Departure days Thu | Cheapest price €184 |
Operator Flixbus USA | Departure Time 01:00PM | Arrival Time 05:33PM | Duration 28h33 | Departure days Fri, Sat, Sun | Cheapest price €204 |
Operator FlixBus | Departure Time 06:00PM | Arrival Time 08:20PM | Duration 26h20 | Departure days Wed, Fri, Sat, Sun | Cheapest price €174 |
Operator Greyhound USA | Departure Time 10:50PM | Arrival Time 06:03AM | Duration 31h13 | Departure days Fri, Sat | Cheapest price €225 |
The table below shows live departures for Chicago, IL to Winter Park, FL buses for tomorrow, Tuesday, September 29. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 3:50 AM Chicago, IL | 30h00 | 9:50 AM Winter Park, FL | 0 transfersDirect | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare train and bus prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Take a bus from Chicago, IL to Winter Park, FL and enjoy the approximately 981 miles (1580 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
The earliest bus runs at 05:15, the last at 23:10.
Distance 981 miles (1580 km) |
First bus 5:15 AM |
Last bus 11:10 PM |
Cheapest Month Mar |
Cheapest Day Thu |
High Season Apr - Jun |
Low Season Jan - Mar |
Discover the best of Winter Park, FL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Winter Park, FL trip today.
Museum housing the world's most comprehensive collection of Louis Comfort Tiffany works, including lamps, windows, and chapel interiors.
Rollins College art museum presenting rotating exhibitions of historic and contemporary works. A strong stop for campus culture and thoughtful curation.
Contemporary visual arts center with gallery exhibitions, classes, and community programs. A good choice for seeing local and regional artists.
Elegant downtown shopping and strolling street lined with boutiques, shaded sidewalks, and historic facades. Ideal for a first walk through Winter Park.
Central downtown green space with lawns, rose gardens, and frequent events. Great for relaxing beside Park Avenue and the nearby train station.
Scenic public garden on Lake Maitland with paths, cypress views, and boardwalk sections. A peaceful local favorite for nature and photography.
Colorado green chili is a pork stew with roasted green chiles, common on burgers, fries, and breakfast plates across mountain towns.
Rocky Mountain trout, usually grilled or pan-fried, reflects Colorado's fishing culture and is a classic mountain-region restaurant dish.
Elk steak is a lean game meat often served in Colorado mountain towns, highlighting the region's ranching and wild game traditions.
Refined cabin-style restaurant focused on steaks, game, and seafood, with a cozy dining room suited to a special night out.
Casual burger spot known for beef, bison, and elk burgers plus fries and shakes in a busy downtown setting.
Popular breakfast and lunch cafe serving burritos, pancakes, and comfort food favorites in a friendly, casual setting.
Winter Park is pricier than many U.S. mountain towns, with higher lodging and dining costs in ski season. Free town transit helps offset transport spending.
Tip 18-20% in restaurants, $1-2 per drink in bars, and round up or tip about 10% for taxis. Cafes often have tip screens; small tips are appreciated.
Find answers to the most common questions about traveling from Chicago, IL to Winter Park, FL by bus. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest bus, the cheapest option, or tips for making the most of your visit at Winter Park, FL, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Winter Park, FL buses use the Chicago, Greyhound Bus Station to Orlando, N John Young Pkwy (Greyhound Bus Station) station pair. Use this guide to compare Chicago, IL and Winter Park, FL bus stations on this route, check city-centre transport, alongside checking practicalities like bus station facilities and services.
Chicago, Greyhound Bus Station is 2 km from Chicago city centre. Public transport options include:
Chicago, Greyhound Bus Station has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food options include: Snack shop and vending machines available
Free Wi-Fi in waiting area. ATMs are located near entrance.
Ticket office support is available at Chicago, Greyhound Bus Station.
Available at Chicago, Greyhound Bus Station: Parking, Taxis, WC.
Accessibility facilities are available at Chicago, Greyhound Bus Station: Wheelchair accessible entrances and seating.
Chicago, Union Station (Amtrak) is 3 km from Chicago city centre. Public transport options include:
Chicago, Union Station (Amtrak) has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food options include: Multiple dining options are available inside the station.
Free Wi-Fi is available in waiting areas. ATMs are aTMs are located near the main entrance.
Ticket office support is available at Chicago, Union Station (Amtrak).
Available at Chicago, Union Station (Amtrak): Parking, Taxis, WC.
Accessibility facilities are available at Chicago, Union Station (Amtrak): Station is accessible with elevators and ramps.
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