- 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.
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The cheapest and fastest buses from Chicago, IL to Winter Park, FL
Showing times, prices and bookable tickets for Sep 30
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
Cheap tickets
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.
Fast buses
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.
3:50 AM30h00Chicago, IL9:50 AMWinter Park, FL€1921One-way0 transfers
- 3:50 AM30h00Chicago, IL9:50 AMWinter Park, FL€1921One-way0 transfers
Chicago, IL to Winter Park, FL Bus Timetables
| 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 |
Live departures
Chicago, IL to Winter Park, FL bus times
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.
Last updated at
| 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 prices and tickets Chicago, IL to Winter Park, FL by train or bus
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.
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Journey information
Overview: Bus from Chicago, IL to Winter Park, FL
USAUSA
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.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
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 |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Bus providers: Greyhound, FlixBus from Chicago, IL to Winter Park, FLYou can travel by bus between Chicago, IL to Winter Park, FL with Greyhound, FlixBus. When you search for schedules and tickets, Omio will show you the best journey
FlixBus
About
FlixBus is one of Europe’s leading low-cost bus companies, founded in Germany and now offering long-distance services across Europe and the United States. In addition to its extensive daytime network, FlixBus also operates overnight buses on select European routes. Standard amenities include free Wi-Fi, power outlets to charge devices, extra legroom, luggage space, and onboard toilets, with snacks and drinks available for purchase. FlixBus offers a single Standard ticket type for all routes, which includes one carry-on bag and one checked bag per passenger. Additional fees apply for extra luggage and for reserving specific seats, such as Extra Seats, Table Seats, or Panorama Seats. This combination of affordability, comfort, and wide coverage makes FlixBus a popular choice for budget-conscious travelers.
Luggage & cancellation policy
Average FlixBus Duration
25h 1m
Cheapest FlixBus Price
€174
FlixBus frequency
3 a day
Luggage included
One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
Additional luggage
Additional luggage can be purchased for a fee.
Cancellation Policy
You can cancel your ticket up to 15 minutes before departure and receive a voucher for future travel. Refund requests for delays over 120 minutes are possible.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority boarding; Wheelchair-accessible buses.
Bikes
Bikes are allowed for a fee; must be booked.
Pets
Small pets in carriers allowed; guide dogs travel for free.
Greyhound
About
Greyhound Lines, Inc. is a prominent American intercity bus transportation provider, established in 1914. It operates the largest intercity bus network in the United States, also extending services to Canada and Mexico. Greyhound is known for offering affordable and reliable long-distance travel, connecting major cities and rural communities across North America. The company's buses are equipped with amenities such as free Wi-Fi, power outlets, and extra legroom to enhance passenger comfort. Greyhound is a subsidiary of Flix SE, which also owns FlixBus, and together they offer an extensive network of over 1,600 destinations.
Luggage & cancellation policy
Average Greyhound Duration
26h 34m
Cheapest Greyhound Price
€225
Greyhound frequency
1 a day
Luggage included
One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
Additional luggage
$15 per additional bag.
Cancellation Policy
You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority seating; Wheelchair-accessible buses.
Bikes
Bikes are allowed.
Complete guide to Winter Park, FL
Things to do in Winter Park, FL
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.
- Recommended
Rollins Museum of Art
Rollins College art museum presenting rotating exhibitions of historic and contemporary works. A strong stop for campus culture and thoughtful curation.
- Recommended
Crealde School of Art
Contemporary visual arts center with gallery exhibitions, classes, and community programs. A good choice for seeing local and regional artists.
- Must visit
Park Avenue
Elegant downtown shopping and strolling street lined with boutiques, shaded sidewalks, and historic facades. Ideal for a first walk through Winter Park.
- Must visit
Central Park
Central downtown green space with lawns, rose gardens, and frequent events. Great for relaxing beside Park Avenue and the nearby train station.
- Recommended
Kraft Azalea Garden
Scenic public garden on Lake Maitland with paths, cypress views, and boardwalk sections. A peaceful local favorite for nature and photography.
- Gluten-free
Colorado Green Chili
Colorado green chili is a pork stew with roasted green chiles, common on burgers, fries, and breakfast plates across mountain towns.
- Gluten-free
Rocky Mountain Trout
Rocky Mountain trout, usually grilled or pan-fried, reflects Colorado's fishing culture and is a classic mountain-region restaurant dish.
- Gluten-free
Elk Steak
Elk steak is a lean game meat often served in Colorado mountain towns, highlighting the region's ranching and wild game traditions.
Deno's Mountain Bistro
Refined cabin-style restaurant focused on steaks, game, and seafood, with a cozy dining room suited to a special night out.
Hernando's Pizza Pub
Casual burger spot known for beef, bison, and elk burgers plus fries and shakes in a busy downtown setting.
The Perk
Popular breakfast and lunch cafe serving burritos, pancakes, and comfort food favorites in a friendly, casual setting.
United States Dollar ($)
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.
Average meal costs
- Budget
- $12-20 for fast food or a casual meal.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $45+ per person for upscale dining.
- Coffee
- $4-7 for coffee or a latte.
Tipping culture
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.
FAQs: Bus from Chicago, IL to Winter Park, FL
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.
The earliest bus from Chicago, IL to Winter Park, FL leaves at 5:15 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Chicago, IL to Winter Park, FL leaves at 11:10 PM.
When taking a bus from Chicago, IL to Winter Park, FL, you can count on Greyhound, FlixBus for the best way to get you to Winter Park, FL. You can also check all possible bus companies who offer a service between Chicago, IL and Winter Park, FL and compare the amenities they offer before buying a bus ticket.
When departing from Chicago, IL , you have various bus station options to start your journey from including Chicago, Greyhound Bus Station, Chicago, Union Station (Amtrak), IL . When arriving in Winter Park, FL , you can end your journey in bus stations like Orlando, N John Young Pkwy (Greyhound Bus Station), Orlando, The Florida Mall, FL .Passengers board the bus most frequently from Chicago, Greyhound Bus Station, which is located around 1 miles (2 km) away from the city centre, and they get off the bus at Orlando, N John Young Pkwy (Greyhound Bus Station), located 3 away from the city centre.
It's helpful to compare your options as there are 2 ways to travel between Chicago, IL and Winter Park, FL including taking a train and bus.
Yes, there are bathrooms on board the bus from Chicago, IL to Winter Park, FL for bus company Greyhound, FlixBus.
Yes, the following accessibility options are available when taking the bus from Chicago, IL to Winter Park, FL:
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
- FlixBus
- Assistance
- Priority boarding
- Wheelchair-accessible buses.
Whether you can cancel your bus ticket from Chicago, IL to Winter Park, FL depends on the bus companies:
- Greyhound
- You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
- FlixBus
- You can cancel your ticket up to 15 minutes before departure and receive a voucher for future travel. Refund requests for delays over 120 minutes are possible.
Yes, bikes are allowed on board the bus with bus company Greyhound, FlixBus.
Tickets are often cheaper when booked early. Traveling during off-peak hours or on weekdays can help you save money. Sort results by price to quickly identify the most affordable options. Check for promotions or discounts available on our website and app.
Yes, there is food available to purchase on board the bus from Chicago, IL to Winter Park, FL.
Yes, the following luggage options are included when booking a bus ticket from Chicago, IL to Winter Park, FL:
- Greyhound
- One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
- FlixBus
- One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
Yes, the following additional luggage options are available when booking a bus ticket from Chicago, IL to Winter Park, FL:
- Greyhound
- $15 per additional bag.
- FlixBus
- Additional luggage can be purchased for a fee.
Yes, you can bring your pet on the bus from Chicago, IL to Winter Park, FL. The following conditions apply:
- FlixBus
- Small pets in carriers allowed
- guide dogs travel for free.
You can reserve your seat on the bus from Chicago, IL to Winter Park, FL with the following bus company: Greyhound, FlixBus
Yes, there are USB plugs on board the bus from Chicago, IL to Winter Park, FL with the following bus company: Greyhound, FlixBus.
Yes, there is Wifi on board the bus from Chicago, IL to Winter Park, FL with the following bus company: Greyhound, FlixBus.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Winter Park, FL, travelers should be cautious of petty theft, especially in crowded areas and parking lots. Common scams include overpriced parking and unauthorized tour operators offering boat rides or carriage tours. It's advisable to use official services, keep valuables secure, and stay aware of surroundings to ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular bus stations
Popular bus stations from Chicago, IL to Winter Park, FL
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.
Departure bus stations in Chicago
Arrival bus stations in Winter Park
Which Chicago, IL station do buses to Winter Park, FL leave from?
Buses from Chicago, IL to Winter Park, FL leave from Chicago, Greyhound Bus Station. The station is 1 miles (3 km) from Chicago, IL city centre at 630 W Harrison St, Chicago, IL 60607, USA.
Chicago, Greyhound Bus Station630 W Harrison St, Chicago, IL 60607, USA
City-centre transport
Getting to Chicago, Greyhound Bus Station from Chicago city centre
Chicago, Greyhound Bus Station is 2 km from Chicago city centre. Public transport options include:
Bus7 · 8m · €3 · every ~6 min
Chicago, Greyhound Bus Station bus station facilities and services
Chicago, Greyhound Bus Station has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food and drink
Food options include: Snack shop and vending machines available
Wi-Fi and ATMs
Free Wi-Fi in waiting area. ATMs are located near entrance.
Tickets and information
Ticket office support is available at Chicago, Greyhound Bus Station.
Parking, taxis and toilets
Available at Chicago, Greyhound Bus Station: Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Chicago, Greyhound Bus Station: Wheelchair accessible entrances and seating.
Chicago, Union Station (Amtrak)Chicago Union Station, 225 S Canal St, Chicago, IL 60606, USA
City-centre transport
Getting to Chicago, Union Station (Amtrak) from Chicago city centre
Chicago, Union Station (Amtrak) is 3 km from Chicago city centre. Public transport options include:
Bus28, 151 · 7m · €3 · every ~13 min
Chicago, Union Station (Amtrak) bus station facilities and services
Chicago, Union Station (Amtrak) has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food and drink
Food options include: Multiple dining options are available inside the station.
Wi-Fi and ATMs
Free Wi-Fi is available in waiting areas. ATMs are aTMs are located near the main entrance.
Tickets and information
Ticket office support is available at Chicago, Union Station (Amtrak).
Parking, taxis and toilets
Available at Chicago, Union Station (Amtrak): Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Chicago, Union Station (Amtrak): Station is accessible with elevators and ramps.
Most popular bus connections from Chicago, IL
More options for your journey from Chicago, IL to Winter Park, FL
Here are some other resources that might have the information you need
Most popular buses to and from Winter Park, FL and Chicago, IL
Most popular bus connections to Winter Park, FL
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