- Must visit
The Charles Hosmer Morse Museum of American Art
Celebrated museum in nearby Winter Park famous for the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Cheapest price
$164
Average price
$176
Fastest journey
1 d 20 m
Average duration
1 d 5 h 32 m
Buses per day
8
Distance
1037 km
The best way to find a cheap bus ticket from Chesapeake, VA to Orlando, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chesapeake, VA to Orlando, FL will cost around $176 if you buy it on the day, but the cheapest tickets can be found for only $164.
It's difficult to get from Chesapeake, VA to Orlando, FL without transferring at least once.
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FlixBus · FlixBusOmio recommends booking the flight as it is the most popular option from Chesapeake, VA to Orlando, FL among Omio's users. If you are prioritising price take the flight with prices starting from $54. For those with little time consider booking a flight which can get you there in 2h 6m. The ticket price range depends on the travel mode: a flight costs an average of $54, and a train costs an average of $203.
Distance: 644 miles (1037 km)
| Bus | Most popular Flight | Train |
|---|---|---|
$231 Average price | $126 Average price Cheapest | $247 Average price |
40h 30m Average total duration 40h 0m Onboard + 30m Additional time* | 5h 6m Average total duration Fastest 2h 6m Onboard + 3h 0m Additional time* | 20h 37m Average total duration 20h 7m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chesapeake, VA to Orlando, FL:
A flight is $106 (€85) less than a bus for this route with tickets for a bus from Chesapeake, VA to Orlando, FL costing on average $231 (€187).
A flight is $122 (€98) less than a train for this route with tickets for a train from Chesapeake, VA to Orlando, FL costing on average $247 (€200).
Other travel options to Orlando, FL take longer:
Train takes on average 20h 7m.
Bus takes on average 40h 0m.
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 07:00AM | Arrival Time 11:59PM | Duration 40h59 | Departure days Mon, Fri | Cheapest price $154 |
Operator FlixBus | Departure Time 07:00AM | Arrival Time 02:10PM | Duration 31h10 | Departure days Mon, Fri | Cheapest price $157 |
Operator Greyhound | Departure Time 07:30AM | Arrival Time 02:55PM | Duration 31h25 | Departure days Mon, Fri | Cheapest price $162 |
Operator FlixBus | Departure Time 08:05AM | Arrival Time 11:59PM | Duration 39h54 | Departure days Mon, Fri | Cheapest price $154 |
Operator Greyhound | Departure Time 11:30AM | Arrival Time 06:55PM | Duration 31h25 | Departure days Sat | Cheapest price $195 |
Operator FlixBus | Departure Time 02:45PM | Arrival Time 09:15PM | Duration 30h30 | Departure days Mon, Fri | Cheapest price $147 |
Operator FlixBus | Departure Time 03:00PM | Arrival Time 09:15PM | Duration 30h15 | Departure days Mon, Fri | Cheapest price $150 |
Operator Hampton Roads Transit (HRT) | Departure Time 05:20PM | Arrival Time 02:10PM | Duration 20h50 | Departure days Sun | Cheapest price $158 |
Operator Greyhound | Departure Time 07:45PM | Arrival Time 04:59AM | Duration 57h14 | Departure days Thu | Cheapest price $294 |
Operator FlixBus | Departure Time 10:00PM | Arrival Time 04:35PM | Duration 42h35 | Departure days Mon, Fri | Cheapest price $149 |
The table below shows live departures for Chesapeake, VA to Orlando, FL buses for today, Thursday, June 4. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 7:45 PM Chesapeake, VA | 57h14 | 4:59 AM Orlando, FL | 0 transfersDirect | |
| Friday, June 5 | |||||
FlixBus · FlixBus | 7:00 AM Virginia Beach, Virginia Beach Blvd (Circle D Food Mart), VA | 31h10 | 2:10 PM Orlando, N John Young Pkwy (Greyhound Bus Station) | 1 transfer | |
FlixBus+ + FlixBus | 7:00 AM Virginia Beach, Virginia Beach Blvd (Circle D Food Mart), VA | 40h59 | 11:59 PM Orlando, The Florida Mall, FL | 2 transfers | |
· + FlixBus | 7:30 AM Norfolk, Poplar Hall Dr (CVS/pharmacy), VA | 24h20 | 7:50 AM Orlando, N John Young Pkwy (Greyhound Bus Station) | 2 transfers | |
· + FlixBus · FlixBus | 7:30 AM Norfolk, Poplar Hall Dr (CVS/pharmacy), VA | 31h25 | 2:55 PM Orlando, The Florida Mall, FL | 3 transfers | |
FlixBus+ · · | 8:05 AM Norfolk, Poplar Hall Dr (CVS/pharmacy), VA | 39h54 | 11:59 PM Orlando, The Florida Mall, FL | 3 transfers | |
FlixBus · FlixBus · FlixBus+![]() | 2:45 PM Virginia Beach, Virginia Beach Blvd (Circle D Food Mart), VA | 30h30 | 9:15 PM Orlando, N John Young Pkwy (Greyhound Bus Station) | 3 transfers | |
FlixBus · FlixBus · FlixBus+![]() | 3:00 PM Norfolk, Poplar Hall Dr (CVS/pharmacy), VA | 30h15 | 9:15 PM Orlando, N John Young Pkwy (Greyhound Bus Station) | 3 transfers | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
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.
Buses from Chesapeake, VA to Orlando, FL run on average 7 times per day, taking around 40h 0m. Cheap bus tickets for this journey start at $187 (€151) but you can travel from only $54 (€43) by flight.
The earliest bus runs at 11:30, the last at 19:45. The fastest bus covers the 644 miles (1037 km) distance in 31h 25m.
Distance 644 miles (1037 km) |
Average bus duration 40h 0m |
Cheapest ticket price $187 (€151) |
Buses per day 7 |
Fastest bus 31h 25m |
First bus 11:30 AM |
Last bus 7:45 PM |
Cheapest Month Jan |
Cheapest Day Sat |
High Season Jan - Mar |
Low Season Oct - Dec |
Discover the best of Orlando — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Orlando trip today.
Celebrated museum in nearby Winter Park famous for the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Established art museum in Loch Haven Park with American art, African art, and rotating exhibitions; a leading cultural stop in the city.
Well-regarded history museum in a restored courthouse covering Central Florida history, tourism, citrus, aviation, and local communities.
Downtown Orlando’s most famous urban park, popular for skyline views, the lake loop, swan boats, events, and easy walking.
Orlando’s best-known tourist corridor, lined with attractions, entertainment complexes, and highly photographed nightlife spots.
Charming, walkable main street area just north of Orlando, loved for its brick streets, boutique atmosphere, and polished local feel.
A pressed sandwich with roast pork, ham, Swiss cheese, pickles, and mustard on Cuban bread. It is a Central Florida staple shaped by the region’s Cuban influences.
Fried alligator tail pieces, usually served with a dipping sauce. This is a classic Florida novelty dish tied to the state’s wetlands and Southern cooking traditions.
A sandwich made with local grouper, often grilled, blackened, or fried. It is one of the most recognizable seafood dishes in Central Florida.
Orlando’s flagship fine-dining destination at Walt Disney World, known for tasting menus, polished service, and special-occasion dining.
Beloved neighborhood bakery and diner famous for Southern comfort food, biscuits, and outstanding pies and cakes.
A well-known Winter Park gastropub near Orlando, celebrated for refined American cooking, strong charcuterie, and a lively upscale-casual atmosphere.
Moderate overall. Theme parks and resort areas are pricey, but casual dining and chain hotels can be reasonable outside peak seasons.
Tip 18-20% at restaurants if service is not included. Tip bartenders USD 1-2 per drink, taxis and rideshares 10-15%, hotel staff USD 1-5, and round up for cafes if desired.
Find answers to the most common questions about traveling from Chesapeake, VA to Orlando, 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 Orlando, FL, this guide helps you travel smarter and with confidence.

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