Trip from Wyndham, VA to Chesapeake, VA

Compiled by the Trip.ovh editorial team · Last recalculated Apr 17, 2026 · Methodology

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

Save up to 28 min

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.

Best Time Drive vs Fly

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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 .

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.

Drive Character

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.

Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.

There are about 25 navigation steps in the underlying route data, so the final approach matters more than the middle miles.

I 64 is the longest continuous segment at about 66.8 miles.

How Hard Is This Drive?

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.

Critical Maneuvers

5 of 16 key points

These are the spots where you need to pay the most attention. Preview them before you drive.

0.1 mi into trip | ~0m in | Wyndham Lake Drive

Turn left onto Wyndham Lake Drive

Navigation decision point

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.

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

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.

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

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

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.

Start on this road

411 ft · 34 sec · this road

Turn left onto Old Greenway Drive

130 ft · 11 sec · Old Greenway Drive

Turn left onto Wyndham Lake Drive

0.3 mi · 36 sec · Wyndham Lake Drive

Turn left onto Wyndham Park Drive

0.4 mi · 57 sec · Wyndham Park Drive

Turn left onto Nuckols Road

2.3 mi · 4 min · Nuckols Road

Take the ramp

0.4 mi · 48 sec

Toward I 295 South: Washington, Norfolk

Merge onto I 295

22 mi · 23 min · Korean War Veterans Memorial Highway

Use the straight / slight right lanes.

Take the exit

1.3 mi · 2 min

Exit 28A Toward I 64 East: Norfolk, Virginia Beach Use the straight / slight right lanes.

Merge onto I 64

67 mi · 1 hr 15 min · I 64

Use the straight / slight right lanes.

Keep slight left at fork onto I 64; US 60

342 ft · 5 sec · Hampton Roads Beltway

Continue on I 64; US 60

3.5 mi · 4 min · Hampton Roads Bridge-Tunnel

Continue on I 64; US 60

6.7 mi · 8 min · Hampton Roads Beltway

Use the straight / slight right lanes.

Take the exit

0.2 mi · 32 sec

Exit 278 Toward VA 194 South: Chesapeake Boulevard Use the slight right lane.

Turn straight onto VA 194

2.1 mi · 3 min · Chesapeake Boulevard

Use the left lane.

Turn straight

135 ft · 7 sec

Turn left onto VA 247

1.1 mi · 1 min · Ballentine Boulevard

Turn right onto VA 166

0.9 mi · 1 min · East Princess Anne Road

Turn left onto VA 166

0.6 mi · 1 min · Park Avenue

Turn left onto US 460; VA 166; VA 168

0.3 mi · 57 sec · East Brambleton Avenue

Use the left / straight / right lanes.

Continue on US 460; VA 166; VA 168

0.7 mi · 1 min · Campostella Road

Turn right onto US 460; VA 166

0.7 mi · 1 min · Wilson Road

Use the right lane.

Continue on US 460; VA 166

0.3 mi · 27 sec · 22nd Street

Continue on US 460; VA 166

0.3 mi · 29 sec · Poindexter Street

Use the straight lane.

Turn right onto D Street

412 ft · 18 sec · D Street

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.

Halfway Point

Midpoint

About 55.6 mi from Wyndham, VA · 1h 6m into the drive

Mid-route town

Meal stop

Williamsburg, VA

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

Highland Springs, VA

Fuel and coffee

A short stop after about 24 miles helps settle the day before fatigue starts building.

Williamsburg, VA

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 check

Top up before I 64 if your tank is already low. That segment runs about 66.8 miles.

Arriving in Chesapeake, VA

The final approach into Chesapeake, VA usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.

Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Chesapeake, VA.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

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	DC Fast	Home Charge
Average EV	33.4	$11.68	$5.34
Efficient EV	27.8	$9.73	$4.45
EV Truck/SUV	44.5	$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.

Forecast as of Apr 15, 2026

Origin

Wyndham, VA

Late night in Wyndham on Friday

Local time

2:50 AM

EDT

Current temp

50°F

Unavailable

Live forecast

Destination

Chesapeake, VA

Late night in Chesapeake on Friday

Local time

2:50 AM

EDT

Current temp

52°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

2 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.

Frequently Asked Questions

The drive from Wyndham, VA to Chesapeake, VA covers 111.2 miles and takes about 2h 17m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are I 64, Korean War Veterans Memorial Highway, Hampton Roads Beltway. Expect a mix of highway and local road driving.

This is a comfortable same-day trip.

The midpoint is about 55.6 miles from Wyndham, VA. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $17.39 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.

On the drive from Wyndham, VA to Chesapeake, VA, road signs begin pointing toward Virginia Beach along the way.

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Explore more options from Wyndham, VA or browse trips ending in Chesapeake, VA.

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Trip from Wyndham, VA to Chesapeake, VA

Best Time to Leave

Trip Overview

Who Is This Route For?

Drive Character

How Hard Is This Drive?

Critical Maneuvers

Towns Mentioned on Route Signs

Main Roads

Turn-by-Turn Driving Directions

Trip Plan

Before You Leave

Where to Stop

Pacing Suggestions

Arriving in Chesapeake, VA

Fuel & Cost

Travel Intel

Wyndham, VA

Chesapeake, VA

Same local time

2 degrees warmer at arrival

2h 17m on the road

Frequently Asked Questions

Explore More

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