How far is Chester, NY from Islip, NY?
The driving distance from Chester, NY to Islip, NY is about 101.4 miles (163.2 km), with a travel time of about 02h 03m by car.
- The straight-line flight distance is about 70.5 miles (113.4 km).
- For a round trip, plan for roughly 04h 06m 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 02h 03m.
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.
City in New York County, New York, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Partly Sunny
Driving Route Map
The map below follows the saved road route between Chester and Islip.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester and Islip.
-
1
Start on Railroad Avenue
104 m · 17 sec · Railroad Avenue
-
2
Turn right onto Bank Street
115 m · 23 sec · Bank Street
-
3
Turn left onto High Street
1482 ft · 29 sec · High Street
-
4
Continue on Main Street
1475 ft · 31 sec · Main Street
-
5
Turn right onto Academy Avenue
1281 ft · 28 sec · Academy Avenue
-
6
Continue on State Highway 94
953 ft · 30 sec · State Highway 94
-
7
Take the ramp left toward US 6 East, NY 17 East: Monroe
1480 ft · 36 sec
-
8
Merge slight left
8.4 mi · 10 min
-
9
Keep slight left to continue on I 87, NYST: Albany, New York City
1.1 km · 60 sec
-
10
Keep slight right to continue on I 87 Toll South: New York City
1.5 km · 2 min
-
11
Merge slight left onto New York State Thruway
13.7 mi · 16 min · New York State Thruway
-
12
Keep slight right to continue on I 287 South, NJ 17 South: New Jersey
1.5 km · 60 sec
-
13
Continue straight
2496 ft · 39 sec
-
14
Keep slight left to continue on NJ 17 South: Mahwah
14.1 mi · 19 min
-
15
Take the exit slight right toward NJ 4, GSP South: Paterson, Fort Lee, New York
566 ft · 19 sec
-
16
Keep slight left to continue on NJ 4 East: Fort Lee, New York
2455 ft · 1 min
-
17
Merge slight left
1417 ft · 24 sec
-
18
Continue straight
6.4 mi · 9 min
-
19
Take the exit slight left toward I 95 North: George Washington Bridge
1124 ft · 18 sec
-
20
Merge slight left
1.2 km · 55 sec
-
21
Keep slight left
1.3 km · 1 min
-
22
Continue on George Washington Bridge (upper level)
3174 ft · 1 min · George Washington Bridge (upper level)
-
23
Continue on Trans-Manhattan Expressway
1.2 km · 1 min · Trans-Manhattan Expressway
-
24
Continue on Cross Bronx Expressway
4.7 mi · 6 min · Cross Bronx Expressway
-
25
Keep slight right to continue on Cross Bronx Expressway
2 mi · 3 min · Cross Bronx Expressway
-
26
Merge slight left onto Throgs Neck Expressway
3271 ft · 58 sec · Throgs Neck Expressway
-
27
Continue on Throgs Neck Bridge
2 mi · 3 min · Throgs Neck Bridge
-
28
Continue on Clearview Expressway
5 mi · 5 min · Clearview Expressway
-
29
Continue on Hollis Court Boulevard
1.2 km · 1 min · Hollis Court Boulevard
-
30
At the end of the road, turn left onto Jamaica Avenue
1117 ft · 35 sec · Jamaica Avenue
-
31
Turn right onto Hempstead Avenue
1.4 km · 2 min · Hempstead Avenue
-
32
Turn right onto 225th Street
69 m · 10 sec · 225th Street
-
33
Take the ramp straight toward Cross Island Parkway South, Verrazano Bridge
1171 ft · 29 sec
-
34
Merge slight left onto Cross Island Parkway
1.3 mi · 2 min · Cross Island Parkway
-
35
Take the exit slight left toward Southern State Parkway East, Eastern Long Island
2383 ft · 1 min
-
36
Merge slight left onto Southern State Parkway
24.5 mi · 31 min · Southern State Parkway
-
37
Keep slight left to continue on Southern State Parkway
1072 ft · 16 sec · Southern State Parkway
-
38
Take the exit slight right toward Bay Shore Road South, Bay Shore
1044 ft · 32 sec
-
39
Turn straight onto Bay Shore Road
2667 ft · 1 min · Bay Shore Road
-
40
Continue on Howells Road
1845 ft · 44 sec · Howells Road
-
41
Turn straight onto Sunrise Highway
104 m · 7 sec · Sunrise Highway
-
42
Keep slight right to continue on Howells Road
3115 ft · 2 min · Howells Road
-
43
Continue on Roosevelt Street
1248 ft · 25 sec · Roosevelt Street
-
44
Continue on 3rd Avenue
1 km · 1 min · 3rd Avenue
-
45
At the end of the road, turn left onto East Main Street
1.1 mi · 2 min · East Main Street
-
46
Continue on Montauk Highway
1014 ft · 17 sec · Montauk Highway
-
47
Continue on Main Street
1.2 km · 1 min · Main Street
-
48
Arrive at your destination
0 m · 1 sec · Main Street
Car Route Details
A richer read on the saved driving route between Chester and Islip.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Southern State Parkway
Merge slight left onto Southern State Parkway
24.5 mi · 00h 31m
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.
Mostly Sunny leaving Chester and Partly Sunny near Islip.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chester to Islip?
The road trip is about 101.4 miles (163.2 km) and usually takes 02h 03m 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?
Inwood is a useful midpoint, sitting about 49.1 miles from Chester and 52.3 miles from Islip.
How much longer is the road route than the straight-line distance?
The direct path is about 70.5 miles (113.4 km), while the road route adds roughly 30.9 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 2:24 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $14.35 one way or $28.70 round trip. Estimated CO2 is about 31.8 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Chester and Partly Sunny near Islip.
Stop Ideas Near Inwood
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
City Hall Parking Lot
#Artlook New York City Hall Wedding Photographer
City Hall Personnel Office
Diamond City Hall Photography
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Inwood.
Yonkers station
New Rochelle station
Pennsylvania Station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Chester and Islip. Straight-line distance: 70.48 mi (113.42 km).
#1 Chester
Village in Orange County, New York
| Population | 3,247 |
| Coordinates | 41.3625900, -74.2712600 |
| Altitude | 146 |
| Country | United States |
#2 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 |
End: Main Street (-73.210382, 40.729789)
Estimated Travel Time
Distance: 163 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 22m |
| 40 mph (64.37 km/h) | 02h 32m |
| 50 mph (80.47 km/h) | 02h 01m |
| 60 mph (96.56 km/h) | 01h 41m |
| 70 mph (112.65 km/h) | 01h 26m |
| 80 mph (129 km/h) | 01h 15m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.01 | $14.35 | $28.70 |
| Mid-grade | $4.48 | $16.04 | $32.08 |
| Premium | $4.86 | $17.40 | $34.80 |
| Diesel | $4.69 | $16.80 | $33.61 |
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.