4.9
4.6The cheapest and fastest buses from Chicago, IL to Winter Park, FL
Cheapest price
$213
Average price
$254
Fastest journey
1 d 1 h 3 m
Average duration
1 d 3 h 1 m
Buses per day
4
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 $254 if you buy it on the day, but the cheapest tickets can be found for only $213.
It's difficult to get from Chicago, IL to Winter Park, FL without transferring at least 3 times.
6:00 PM28h01Chicago, IL10:01 PMWinter Park, FL$2131One-way3 transfers- 1:00 PM28h26Chicago, IL5:26 PMWinter Park, FL$2491One-way3 transfers
6:10 AM26h34Chicago, IL8:44 AMWinter Park, FL$2751One-way3 transfers- 6:00 PM25h03Chicago, IL7:03 PMWinter Park, FL$2811One-way5 transfers
- 6:00 PM25h03Chicago, IL7:03 PMWinter Park, FL$2811One-way5 transfers
- 6:10 AM26h34Chicago, IL8:44 AMWinter Park, FL$2751One-way3 transfers
- 6:00 PM28h01Chicago, IL10:01 PMWinter Park, FL$2131One-way3 transfers
- 1:00 PM28h26Chicago, IL5:26 PMWinter Park, FL$2491One-way3 transfers
Travel Information
Compare train, bus, and flight for Chicago, IL to Winter Park, FL
Omio recommends booking the bus as it is the most popular option from Chicago, IL to Winter Park, FL among Omio's users. If you are prioritising price take the flight with prices starting from $61. For those with little time consider booking a flight which can get you there in 4h 4m. The ticket price range depends on the travel mode: a flight costs an average of $61, and a train costs an average of $394.
Distance: 981 miles (1580 km)
Compare bus with
Most popular Bus | Train | Flight | Driving |
|---|---|---|---|
$238 Average price | $461 Average price | $144 Average price Cheapest | $224 Average price (fuel + tolls) |
29h 46m Average total duration 29h 16m Onboard + 30m Additional time* | 39h 25m Average total duration 38h 55m Onboard + 30m Additional time* | 7h 4m Average total duration Fastest 4h 4m Onboard + 3h 0m Additional time* | 17h 26m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Winter Park, FL:
A flight is $94 (€77) less than a bus for this route with tickets for a bus from Chicago, IL to Winter Park, FL costing on average $238 (€195).
A flight is $317 (€260) less than a train for this route with tickets for a train from Chicago, IL to Winter Park, FL costing on average $461 (€377).
Other travel options to Winter Park, FL take longer:
Bus takes on average 29h 16m.
Train takes on average 38h 55m.
You'll arrive about {timeSavings} sooner ({durationInMinutes} by bus vs {drivingDurationInMinutes} by car) and save roughly {savingsAmount} compared to fuel and tolls ({cheapestPrice} vs {drivingPriceInCents}). You also skip the drive itself — no traffic stress, no parking, and you can use the time to work, nap, or catch up on a series with the onboard Wi-Fi.
Direct coaches are operated by {directProviders}.
Driving is still worth considering if you're travelling with bulky luggage, need flexibility on departure times, or plan to stop along the way.
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 $231 |
Operator Greyhound | Departure Time 03:50AM | Arrival Time 09:50AM | Duration 30h00 | Departure days Wed | Cheapest price $235 |
Operator Greyhound USA | Departure Time 06:10AM | Arrival Time 09:02AM | Duration 26h52 | Departure days Fri, Sat, Sun | Cheapest price $275 |
Operator Greyhound | Departure Time 11:10AM | Arrival Time 06:55PM | Duration 31h45 | Departure days Thu | Cheapest price $225 |
Operator Flixbus USA | Departure Time 01:00PM | Arrival Time 05:33PM | Duration 28h33 | Departure days Fri, Sat, Sun | Cheapest price $249 |
Operator FlixBus | Departure Time 06:00PM | Arrival Time 08:20PM | Duration 26h20 | Departure days Wed, Fri, Sat, Sun | Cheapest price $213 |
Operator Greyhound USA | Departure Time 10:50PM | Arrival Time 06:03AM | Duration 31h13 | Departure days Fri, Sat | Cheapest price $275 |
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 today, Saturday, June 20. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 10:50 PM Chicago, IL | 31h11 | 6:01 AM Winter Park, FL | 3 transfers | |
| Sunday, June 21 | |||||
| 6:10 AM Chicago, IL | 26h34 | 8:44 AM Winter Park, FL | 3 transfers | |
| 1:00 PM Chicago, IL | 28h26 | 5:26 PM Winter Park, FL | 3 transfers | |
| 6:00 PM Chicago, IL | 25h03 | 7:03 PM Winter Park, FL | 5 transfers | |
| 6:00 PM Chicago, IL | 28h01 | 10:01 PM Winter Park, FL | 3 transfers | |
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Winter Park, FL by train, bus, or flight
Compare train, bus, and flight 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.
Jun 21
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Jun 23
Jun 24
Jun 25
Jun 26
Jun 27
Why should you book Chicago, IL to Winter Park, FL buses with Omio?
Why book with Omio vs Greyhound?
- Compare with other providers: On Omio, you can not only buy tickets for Greyhound, but also compare tickets for the likes of FlixBus to find the best option for your trip from Chicago, IL to Winter Park, FL.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Greyhound with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Chicago, IL to Winter Park, FL.
Why book with Omio over Wanderu or Trainline?
- Compare with other providers: On Omio, you can also compare tickets for the likes of FlixBus to find the best option for your trip from Chicago, IL to Winter Park, FL.
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Chicago, IL to Winter Park, FL.
Journey information
Overview: Bus from Chicago, IL to Winter Park, FL
USAUSA
Buses from Chicago, IL to Winter Park, FL run on average 9 times per day, taking around 29h 16m. Cheap bus tickets for this journey start at $225 (€184) but you can travel from only $61 (€50) by flight.
The earliest bus runs at 05:15, the last at 23:10. The fastest bus covers the 981 miles (1580 km) distance in 26h 20m.
Distance 981 miles (1580 km) |
Average bus duration 29h 16m |
Cheapest ticket price $225 (€184) |
Buses per day 9 |
Fastest bus 26h 20m |
First bus 5:15 AM |
Last bus 11:10 PM |
Cheapest Month Mar |
Cheapest Day Thu |
High Season Apr - Jun |
Low Season Jan - Mar |
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 for as low as $61 (€50). When you search for schedules and tickets, Omio will show you the best journey
FlixBus
Greyhound
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.
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
- FlixBus
- Assistance
- Priority boarding
- Wheelchair-accessible buses.
- 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.
- 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).
- Greyhound
- $15 per additional bag.
- FlixBus
- Additional luggage can be purchased for a fee.
- FlixBus
- Small pets in carriers allowed
- guide dogs travel for free.
popular bus stations
Popular bus stations from Chicago, IL to Winter Park, FL
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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