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Trip from Naperville, IL to Winnetka, IL

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Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Sep 4, 2026 · Editorial standards

Drive Time

59m

Distance

39.9 mi

64 km

Drive Score

6/10

Good drive

Same Day?

Yes, doable

Fuel Cost

$6

one way

EV Charging

Unknown

Best Time to Leave

Save up to 14 min
4 AM
0h 55m ★
6 AM
0h 59m
8 AM
1h 9m
10 AM
1h 3m
12 PM
1h 2m
3 PM
1h 3m
5 PM
1h 9m
8 PM
0h 57m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

Best Time
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Downtown Naperville, IL, IL

Naperville, IL

Wikimedia Commons

village in Cook County, Illinois, United States

Winnetka, IL

Wikimedia Commons

Trip Overview

The drive from Naperville, IL to Winnetka, IL covers 39.9 miles and takes about 59m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on Tri-State Tollway, Ronald Reagan Memorial Tollway, Willow Road for much of the mileage, and the overall profile is mostly surface roads. The longest uninterrupted segment is about 17.1 miles on Tri-State Tollway. At current regular gas prices, budget about $6.19 one way before food or hotel costs.

Main Roads

Road Distance Duration
Tri-State Tollway 17.1 mi 21m
Ronald Reagan Memorial Tollway 11.6 mi 14m
Willow Road 6.6 mi 12m
East Ogden Avenue 1.6 mi 3m
Locust Road 0.5 mi 1m
Naperville Road 0.3 mi <1m
Pine Street 0.3 mi <1m
North Naperville Wheaton Road 0.3 mi <1m
Longest stretch: Tri-State Tollway — 17.1 mi, about 21m

Turn-by-Turn Driving Directions

Step-by-step road directions between Naperville, IL and Winnetka, IL.

1

Start on North Washington Street

50 ft · 9 sec · North Washington Street
2

Turn left onto US 34

1.6 mi · 3 min · East Ogden Avenue
Use the left lane.
3

Turn left onto North Naperville Wheaton Road

0.3 mi · 39 sec · North Naperville Wheaton Road
Use the left lane.
4

Turn left onto Naperville Road

0.3 mi · 38 sec · Naperville Road
Use the left / straight / right lanes.
5

Take the ramp

0.4 mi · 48 sec
Toward I 88 Toll East: Chicago Use the right lane.
6

Merge onto I 88; IL 110

6.9 mi · 8 min · Ronald Reagan Memorial Tollway
7

Keep slight right at fork onto I 88; IL 110

4.7 mi · 5 min · Ronald Reagan Memorial Tollway
Use the straight / slight right lanes.
8

Take the exit

0.6 mi · 1 min
Exit 139 Toward I 294 North, I 290 West: Milwaukee, Rockford Use the straight / slight right lanes.
9

Keep slight left at fork

0.2 mi · 28 sec
Toward I 294 Toll North: O'Hare International Airport, Milwaukee
10

Merge onto I 294

17 mi · 21 min · Tri-State Tollway
Use the straight / slight right lanes.
11

Take the exit

0.1 mi · 15 sec
Exit 48 Toward Willow Road Use the slight right lane.
12

Continue on this road

0.2 mi · 26 sec · this road
Exit 48 Toward Willow Road
13

Turn right onto Willow Road

5.2 mi · 10 min · Willow Road
Use the left lane.
14

Continue on Willow Road

1.4 mi · 2 min · Willow Road
15

Turn left onto Locust Road

0.5 mi · 1 min · Locust Road
16

Turn right onto Pine Street

0.3 mi · 43 sec · Pine Street
17

Arrive at destination

Pine Street

Where to Stop

Rest stops, refuel points, and overnight suggestions along this route.

city in Illinois, United States

Mid-route town

Meal stop

Elmhurst, IL

20 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.

Popular next leg

Elmhurst, IL to Winnetka, IL

24.7 mi · 40m

Pacing Suggestions

Evanston, IL

Fuel and coffee

A short stop after about 39.9 miles helps settle the day before fatigue starts building.

Elmhurst, IL

Meal break

The midpoint is around 19.9 miles from Naperville, IL, which is a good place for a longer meal and fuel stop.

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 14

5 decision points cluster between mile 0 and 32.2 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.

6
0 mi into trip | ~0m in | US 34 / East Ogden Avenue

Turn left onto US 34 / East Ogden Avenue

Lane positioning matters here

Use the left lane.
6
9.5 mi into trip | ~14m in | I 88; IL 110 / Ronald Reagan Memorial Tollway

Keep slight right at fork onto I 88; IL 110 / Ronald Reagan Memorial Tollway

Highway fork - watch signs carefully. Lane positioning matters here

Use the straight / slight right lanes.
8
14.2 mi into trip | ~20m in

Take the exit toward I 294 North, I 290 West: Milwaukee, Rockford

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 139 Toward I 294 North, I 290 West: Milwaukee, Rock...
6
14.8 mi into trip | ~21m in

Keep slight left at fork toward I 294 Toll North: O'Hare International Airport, Milwaukee

Highway fork - watch signs carefully. Multiple destination signs - pick the right one

Toward I 294 Toll North: O'Hare International A...
7
32.2 mi into trip | ~44m in

Take the exit toward Willow Road

Exit ramp - move to the correct lane early. Lane positioning matters here

Use the slight right lane. Exit 48 Toward Willow Road

Fuel & Cost

Regular Gas

$6.19 one way

$12.37 round trip

$3.94/gal 25.4 MPG avg 14 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.32 $6.78 $13.57
premium $4.93 $7.74 $15.48
diesel $5.60 $8.80 $17.59

Estimated Tolls: $1.72

Tri-state Tollway (17.1 mi) $1.03
Reagan Memorial Tollway (11.6 mi) $0.69

Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.

Drive Cost (one way)

Fuel

$6

Tolls

$2

Total

$8

Estimated CO2 emission: 14 kg one way. Prices: EIA weekly data, 2026-08-31.

Driving Electric?

About $4 in charging · 0 stops · 64% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 12 0 $4.19 $1.92
Efficient EV 10 0 $3.49 $1.60
EV Truck/SUV 16 0 $5.59 $2.55

Gas CO2

14 kg

EV CO2

5 kg (64% 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 Sep 2, 2026

Origin

Naperville, IL

Late night in Naperville on Friday

Local time

2:49 AM

CDT

Current temp

74°F

Mostly Clear

SSW 5 mph 0% chance Live forecast

Heat Advisory

Heat Advisory issued September 2 at 1:20AM CDT until September 3 at 7:00PM CDT by NWS Quad Cities IA IL

Heat Advisory

Heat Advisory issued September 2 at 1:20AM CDT until September 3 at 7:00PM CDT by NWS Quad Cities IA IL

Destination

Winnetka, IL

Late night in Winnetka on Friday

Local time

2:49 AM

CDT

Current temp

76°F

Mostly Clear

SW 5 to 10 mph 0% chance Live forecast

Heat Advisory

Heat Advisory issued September 2 at 1:20AM CDT until September 3 at 7:00PM CDT by NWS Quad Cities IA IL

Heat Advisory

Heat Advisory issued September 2 at 1:20AM CDT until September 3 at 7:00PM CDT by NWS Quad Cities IA IL

85°F

Elmhurst, IL

20 mi in

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

59m on the road

The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.

Weather data from the National Weather Service. Conditions may change; check closer to your travel date.

What kind of drive is this?

39.9 mi in 59m across surface roads — expect steady turns and local traffic rather than long highway runs.

Only 0% highway — the rest is turn-by-turn surface driving.
17 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 17.1 mi on Tri-State Tollway.

How Hard Is This Drive?

9/10

Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes early in the drive near US 34 / East Ogden Avenue.

Driving Effort 9/10

Focused - lots of decisions in a short distance, but it is over quickly

Balances navigation complexity with total wheel time.

This is a short but busy drive. With 14 decision points packed into just 39.9 miles, you will need to pay attention to lane changes and exits — but the whole thing is over in 59m.

Where does it get tricky?

The main spots that need attention: near the start (US 34 / East Ogden Avenue): Lane positioning matters here; at 9.5 miles (I 88; IL 110 / Ronald Reagan Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 14.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.

Elevation Profile

Mostly flat terrain

753 ft 635 ft

Total Climb

129 ft

Total Descent

184 ft

Highest Point

753 ft

~5.7 mi in

Elevation Range

118 ft

Towns Mentioned on Route Signs

Based on OSRM destination-sign hints, not a full list of every settlement the road passes.

Between Naperville, IL and Winnetka, IL, road signs point toward Rockford and Milwaukee.

Rockford

14.2 mi in | ~20m

Milwaukee

14.8 mi in | ~21m

About the Cities

Starting in Naperville, IL

Full guide →

Founded 1890

Naperville is a bedroom community in the Chicagoland area. In 2008, Money magazine ranked Naperville third on its list of the 100 best places to live in the United States.

Arriving in Winnetka, IL

Full guide →

Founded 1869

Winnetka is a village on Illinois' North Shore, in the Chicagoland region of Illinois.

Top landmarks

  • • Crow Island School — school building in Winnetka, United States of America
  • • Winnetka Community House — social, civic - center, buildings
  • • Dr. Paul W. and Eunice Greeley House — historic residence in Winnetka, Illinois

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 59m. Total distance: 39.9 miles.

Family Friendly

Moderate complexity with 0 natural rest stops along the way.

Solo Traveler

59m drive, comfortable solo distance.

EV Driver

0 DC fast chargers along the route. Coverage: unknown.

Scenic Drive

Mostly surface roads route profile with national parks nearby.

Frequently Asked Questions

The longest stretch is about 17.1 miles on Tri-State Tollway. The full list of main roads is in the Roads section above.

Expect about $1.72 in tolls one way, starting with Tri-state Tollway. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.

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 Winnetka, IL before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.

Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.

The main spots that need attention: near the start (US 34 / East Ogden Avenue): Lane positioning matters here; at 9.5 miles (I 88; IL 110 / Ronald Reagan Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 14.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.

Yes — Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.

Yes. A round trip is manageable in a single day if you plan a break at Winnetka, IL 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, EIA for fuel prices, USGS 3DEP for elevation, and NPS for national parks. See our methodology for refresh cadence and limitations.

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