How far is Islip, NY from Chappaqua, NY?
The driving distance from Islip, NY to Chappaqua, NY is about 69 miles (111 km), with a travel time of about 01h 40m by car.
- The straight-line flight distance is about 41.4 miles (66.7 km).
- For a round trip, plan for roughly 03h 21m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 01h 40m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Census-designated place in Ulster County, New York
Route Weather Snapshot
Check the forecast at both ends before you head out.
Rain Showers Likely
Showers And Thunderstorms Likely
Driving Route Map
The map below follows the saved road route between Islip and Chappaqua.
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip and Chappaqua.
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1
Start on Main Street
1.2 km · 1 min · Main Street
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2
Continue on Montauk Highway
1014 ft · 19 sec · Montauk Highway
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3
Continue on Main Street
1.1 mi · 2 min · Main Street
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4
Turn right onto 3rd Avenue
2920 ft · 1 min · 3rd Avenue
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5
Continue on Rossevelt Street
1821 ft · 37 sec · Rossevelt Street
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6
Continue on Howells Road
1.1 km · 2 min · Howells Road
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7
Turn straight onto Sunrise Highway
50 m · 3 sec · Sunrise Highway
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8
Keep slight right to continue on Howells Road
1588 ft · 36 sec · Howells Road
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9
Continue on Bay Shore Road
3165 ft · 1 min · Bay Shore Road
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10
Take the ramp slight right toward SO West: New York
736 ft · 19 sec
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11
Continue straight
111 m · 9 sec
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12
Merge slight left onto Southern State Parkway
24.7 mi · 32 min · Southern State Parkway
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13
Take the exit slight right toward Cross Island Parkway North, Whitestone Bridge
1780 ft · 43 sec
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14
Merge slight left onto Cross Island Parkway
1.3 mi · 2 min · Cross Island Parkway
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15
Take the exit slight right toward NY 24: UBS Arena-Belmont Park
97 m · 9 sec
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16
Keep slight left to continue on NY 24 West: Hempstead Avenue
133 m · 12 sec
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17
Keep slight right to continue on Cross Island Parkway North, Hempstead Avenue West
532 ft · 15 sec
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18
Keep slight right to continue on Hempstead Avenue West
81 m · 8 sec
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19
Continue on Grandstand, Hempstead Avenue West
549 ft · 14 sec
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20
Keep slight left to continue on Hempstead Avenue
31 m · 5 sec
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21
Turn right onto Hempstead Avenue
1.6 km · 2 min · Hempstead Avenue
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22
Turn left onto Jamaica Avenue
553 ft · 17 sec · Jamaica Avenue
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23
Turn right onto 212th Street
1.2 km · 1 min · 212th Street
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24
Continue on Clearview Expressway
5 mi · 5 min · Clearview Expressway
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25
Continue on Throgs Neck Bridge
2 mi · 3 min · Throgs Neck Bridge
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26
Continue on Throgs Neck Expressway
1.1 km · 1 min · Throgs Neck Expressway
-
27
Keep slight right to continue on Throgs Neck Expressway
1.8 mi · 3 min · Throgs Neck Expressway
-
28
Merge slight right onto Bruckner Expressway
1 mi · 2 min · Bruckner Expressway
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29
Continue on New England Thruway
1074 ft · 18 sec · New England Thruway
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30
Take the exit slight right toward Hutchinson Parkway North
131 m · 15 sec
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31
Keep slight left to continue on Hutchinson River Parkway North
912 ft · 31 sec
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32
Merge slight left onto Hutchinson River Parkway
13.5 mi · 19 min · Hutchinson River Parkway
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33
Keep slight left to continue on I 684 North: Brewster
1.6 mi · 2 min
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34
Merge slight right
3 mi · 4 min
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35
Take the exit slight right toward NY 120: Westchester County Airport
1110 ft · 28 sec
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36
Turn slight right onto Airport Road
37 m · 7 sec · Airport Road
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37
Turn left onto Lake Street
2569 ft · 53 sec · Lake Street
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38
Continue on King Street
1.5 mi · 3 min · King Street
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39
Turn right onto Mount Kisco Road
644 ft · 15 sec · Mount Kisco Road
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40
Continue on King Street
1110 ft · 23 sec · King Street
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41
Turn left onto King Street
4.1 mi · 7 min · King Street
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42
At the end of the road, turn right onto State Highway 117
138 m · 16 sec · State Highway 117
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43
Turn sharp left
49 m · 7 sec
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44
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Islip and Chappaqua.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Southern State Parkway
Merge slight left onto Southern State Parkway
24.7 mi · 00h 32m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Rain Showers Likely leaving Islip and Showers And Thunderstorms Likely near Chappaqua.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Islip to Chappaqua?
The road trip is about 69 miles (111 km) and usually takes 01h 40m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Hillside is a useful midpoint, sitting about 34.5 miles from Islip and 34.5 miles from Chappaqua.
How much longer is the road route than the straight-line distance?
The direct path is about 41.4 miles (66.7 km), while the road route adds roughly 27.6 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 3:08 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $9.78 one way or $19.56 round trip. Estimated CO2 is about 21.7 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers Likely around Islip and Showers And Thunderstorms Likely near Chappaqua.
Stop Ideas Near Hillside
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Radio City Music Hall
The Yard: City Hall Park NYC
CITY HALL LOBBY
Town Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Hillside.
Pennsylvania Station
New Rochelle station
Yonkers station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Islip and Chappaqua. Straight-line distance: 41.46 mi (66.72 km).
#1 Islip
This Long Island community is situated on the south shore of Suffolk County, New York, at an elevation of 13 feet.
| Population | 322,328 |
| Coordinates | 40.7298200, -73.2103900 |
| Altitude | 4 |
| Country | United States |
#2 Chappaqua
Census-designated place in New York
| Population | 1,436 |
| Coordinates | 41.1595400, -73.7648500 |
| Altitude | 150 |
| Country | United States |
End: Chappaqua (-73.76485, 41.15954)
Estimated Travel Time
Distance: 111 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 17m |
| 40 mph (64.37 km/h) | 01h 43m |
| 50 mph (80.47 km/h) | 01h 22m |
| 60 mph (96.56 km/h) | 01h 08m |
| 70 mph (112.65 km/h) | 00h 59m |
| 80 mph (129 km/h) | 00h 51m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.01 | $9.78 | $19.56 |
| Mid-grade | $4.48 | $10.93 | $21.87 |
| Premium | $4.86 | $11.86 | $23.72 |
| Diesel | $4.69 | $11.45 | $22.91 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in New York · Apr 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.