Origin
Wyndham, VA
Morning in Wyndham on Sunday
Local time
10:17 AM
EDT
Current temp
50°F
Unavailable
Live forecast
Trip from Wyndham, VA to Chesapeake, VA
Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 19, 2026 · Editorial standards
Drive Time
2h 17m
Distance
111.2 mi
179 km
Drive Score
9/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$17
one way
EV Charging
Unknown
Best Time to Leave
4 AM
2h 8m
★
6 AM
2h 17m
8 AM
2h 36m
10 AM
2h 24m
12 PM
2h 22m
3 PM
2h 25m
5 PM
2h 35m
8 PM
2h 12m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Wyndham, VA
Eric Joseph
Chesapeake, VA
Wikimedia Commons
Trip Overview
Planning a trip from Wyndham to Chesapeake, Virginia? This 111.2-mile drive will take you about 2 hours and 17 minutes, making it a perfect candidate for a single-day road trip. You'll primarily be on I-64 and the Hampton Roads Beltway, with about 60% of the journey on highways. The estimated fuel cost for this route is around $17, offering a budget-friendly option for exploring within the Southeast region. This straightforward route keeps you moving efficiently through Virginia.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
55.6 miles from Wyndham, VA
A natural place for your longest stop of the day , about 1h 6m into the drive .
Main Roads
| Road | Distance | Duration |
|---|---|---|
| I 64 | 66.8 mi | 1h 15m |
| Korean War Veterans Memorial Highway | 21.9 mi | 23m |
| Hampton Roads Beltway | 6.8 mi | 8m |
| Hampton Roads Bridge-Tunnel | 3.5 mi | 4m |
| Nuckols Road | 2.3 mi | 4m |
| Chesapeake Boulevard | 2.1 mi | 3m |
| Ballentine Boulevard | 1.1 mi | 1m |
| East Princess Anne Road | 0.9 mi | 1m |
Longest stretch:
I 64
— 66.8 mi, about 1h 15m
Turn-by-Turn Driving Directions
Step-by-step road directions between Wyndham, VA and Chesapeake, VA.
1
Start on this road
411 ft
·
34 sec
·
this road
2
Turn left onto Old Greenway Drive
130 ft
·
11 sec
·
Old Greenway Drive
3
Turn left onto Wyndham Lake Drive
0.3 mi
·
36 sec
·
Wyndham Lake Drive
4
Turn left onto Wyndham Park Drive
0.4 mi
·
57 sec
·
Wyndham Park Drive
5
Turn left onto Nuckols Road
2.3 mi
·
4 min
·
Nuckols Road
6
Take the ramp
0.4 mi
·
48 sec
Toward I 295 South: Washington, Norfolk
7
Merge onto I 295
22 mi
·
23 min
·
Korean War Veterans Memorial Highway
Use the straight / slight right lanes.
8
Take the exit
1.3 mi
·
2 min
Exit 28A
Toward I 64 East: Norfolk, Virginia Beach
Use the straight / slight right lanes.
9
Merge onto I 64
67 mi
·
1 hr 15 min
·
I 64
Use the straight / slight right lanes.
10
Keep slight left at fork onto I 64; US 60
342 ft
·
5 sec
·
Hampton Roads Beltway
11
Continue on I 64; US 60
3.5 mi
·
4 min
·
Hampton Roads Bridge-Tunnel
12
Continue on I 64; US 60
6.7 mi
·
8 min
·
Hampton Roads Beltway
Use the straight / slight right lanes.
13
Take the exit
0.2 mi
·
32 sec
Exit 278
Toward VA 194 South: Chesapeake Boulevard
Use the slight right lane.
14
Turn straight onto VA 194
2.1 mi
·
3 min
·
Chesapeake Boulevard
Use the left lane.
15
Turn straight
135 ft
·
7 sec
16
Turn left onto VA 247
1.1 mi
·
1 min
·
Ballentine Boulevard
17
Turn right onto VA 166
0.9 mi
·
1 min
·
East Princess Anne Road
18
Turn left onto VA 166
0.6 mi
·
1 min
·
Park Avenue
19
Turn left onto US 460; VA 166; VA 168
0.3 mi
·
57 sec
·
East Brambleton Avenue
Use the left / straight / right lanes.
20
Continue on US 460; VA 166; VA 168
0.7 mi
·
1 min
·
Campostella Road
21
Turn right onto US 460; VA 166
0.7 mi
·
1 min
·
Wilson Road
Use the right lane.
22
Continue on US 460; VA 166
0.3 mi
·
27 sec
·
22nd Street
23
Continue on US 460; VA 166
0.3 mi
·
29 sec
·
Poindexter Street
Use the straight lane.
24
Turn right onto D Street
412 ft
·
18 sec
·
D Street
25
Arrive at destination
D Street
Trip Plan
With a total duration of just over two hours, this drive from Wyndham to Chesapeake offers great flexibility. You can easily complete it in one day, so consider leaving mid-morning to avoid early rush hour and arrive in Chesapeake with plenty of daylight. Given the longest stretch is 66.8 miles on I-64, plan for a single fuel or rest stop midway if needed, though it's not strictly necessary for such a short trip. Keep an eye on traffic around the Hampton Roads metropolitan area as you approach Chesapeake, as this can sometimes impact travel times.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 55.6 miles from Wyndham, VA, or about 1h 6m into the drive.
The longest continuous stretch on this route runs about 66.8 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 24 miles or 29m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 55.6 miles or 1h 6m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 46m
Traffic, exits, and arrival timing usually matter more near Chesapeake, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Wyndham, VA so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Wyndham, VA
This is one driving day of about 111.2 miles and 2h 17m.
Your first comfortable stop window is around 24 miles from Wyndham, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on I 64 for about 66.8 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
56 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 24 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 55.6 miles from Wyndham, VA, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel checkTop up before I 64 if your tank is already low. That segment runs about 66.8 miles.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 165 decision points cluster between mile 0.1 and 103.8 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0.1 mi into trip
|
~0m in
|
Wyndham Lake Drive
Turn left onto Wyndham Lake Drive
Navigation decision point
5
3.5 mi into trip
|
~7m in
|
I 295 / Korean War Veterans Memorial Highway
Merge onto I 295 / Korean War Veterans Memorial Highway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
8
25.3 mi into trip
|
~31m in
Take the exit toward I 64 East: Norfolk, Virginia Beach
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 28A
Toward I 64 East: Norfolk, Virginia Beach
5
26.6 mi into trip
|
~34m in
|
I 64
Merge onto I 64
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
7
103.8 mi into trip
|
~2h 2m in
Take the exit toward VA 194 South: Chesapeake Boulevard
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 278
Toward VA 194 South: Chesapeake Boulevard
Fuel & Cost
Regular Gas
$17.39 one way
$34.78 round trip
$3.97/gal
25.4 MPG avg
39 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.34 | $19.01 | $38.03 |
| premium | $4.70 | $20.58 | $41.16 |
| diesel | $5.61 | $24.55 | $49.10 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$17
Meals
$25–$50
Total
$42–$67
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 38.9 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $12 in charging · 0 stops · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 33.4 | 0 | $11.68 | $5.34 |
| Efficient EV | 27.8 | 0 | $9.73 | $4.45 |
| EV Truck/SUV | 44.5 | 0 | $15.57 | $7.12 |
Gas CO2
39 kg
EV CO2
13 kg (67% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Destination
Chesapeake, VA
Morning in Chesapeake on Sunday
Local time
10:17 AM
EDT
Current temp
85°F
Unavailable
Live forecast
71°F
Williamsburg, VA
56 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
35 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
2h 17m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
What kind of drive is this?
This route presents a mixed drive experience, with 60% of the miles on highways. You'll encounter a significant uninterrupted stretch of 66.8 miles on I-64, allowing for steady progress. The majority of your journey will be on main roads like I-64 and the Korean War Veterans Memorial Highway, suggesting a predominantly highway-based experience. Expect a consistent pace for much of the drive, punctuated by transitions between these key routes.
60% highway — fuel and pacing are the main things to plan.
25 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 66.8 mi on I 64.
How Hard Is This Drive?
7/10
This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.1 miles in near Wyndham Lake Drive.
Driving Effort
7/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 16 significant decision points across 111.2 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 0.1 miles (Wyndham Lake Drive): Navigation decision point; at 3.5 miles (I 295 / Korean War Veterans Memorial Highway): Merge point - match speed before joining. Lane positioning matters here; at 25.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
On the drive from Wyndham, VA to Chesapeake, VA, road signs begin pointing toward Virginia Beach along the way.
Virginia Beach
25.3 mi in
|
~31m
About the Cities
Arriving in Chesapeake, VA
Full guide →Chesapeake is a town of 245,000 people (2019) in the Hampton Roads region of Eastern Virginia. Chesapeake is a diverse city in which a few urban areas are located; it also has many square miles of protected farmland, forests, and wetlands, including a substantial portion of the Great Dismal Swamp National Wildlife Refuge.
City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 17m. Total distance: 111.2 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 17m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (60%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 66.8 miles on I 64. The full list of main roads is in the Roads section above.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Chesapeake, VA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 0.1 miles (Wyndham Lake Drive): Navigation decision point; at 3.5 miles (I 295 / Korean War Veterans Memorial Highway): Merge point - match speed before joining. Lane positioning matters here; at 25.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes. A round trip is manageable in a single day if you plan a break at Chesapeake, VA before heading back.
How this page is built
Compiled by the US Trip Planner planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, and EIA for fuel prices. See our methodology for refresh cadence and limitations.
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