Trip from Evanston, IL to Winchester, IL

Data updated 2 hours ago

Drive Time

5h 7m

Distance

264.7 mi

426 km

Drive Score

8/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$41

one way

EV Charging

Excellent

15 DC fast

Best Time to Leave

Save up to 40 min

4 AM

4h 54m ★

6 AM

5h 7m

8 AM

5h 34m

10 AM

5h 17m

12 PM

5h 14m

3 PM

5h 18m

5 PM

5h 33m

8 PM

4h 59m

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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suburban city in Cook County, Illinois, United States

Evanston, IL

Wikimedia Commons

Winchester, IL

Stéphane Tendon

Trip Overview

The drive from Evanston, IL to Winchester, IL covers 264.7 miles and takes about 5h 7m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on Adlai Stevenson Expressway, I 55, I 72 for much of the mileage, and the overall profile is highway-focused drive. The longest uninterrupted segment is about 119.4 miles on Adlai Stevenson Expressway. At current regular gas prices, budget about $41.38 one way before food or hotel costs.

Trip Pace

Same-day drive is realistic

A same-day return is possible, but it will make for a full day on the road.

Break Rhythm

1 planned break

Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.

Midpoint

132.3 miles from Evanston, IL

A natural place for your longest stop of the day , about 2h 41m into the drive .

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Drive Character

This is a 5h 7m highway drive covering 264.7 miles, with most of the trip on Adlai Stevenson Expressway and I 55. The longest continuous stretch is about 119.4 miles on Adlai Stevenson Expressway.

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

There are about 27 navigation steps in the underlying route data, so the final approach matters more than the middle miles.

Adlai Stevenson Expressway is the longest continuous segment at about 119.4 miles.

How Hard Is This Drive?

This is a straightforward highway drive that stays mostly on Adlai Stevenson Expressway and I 55. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes early in the drive.

Route Complexity 8/10

Demanding - plan breaks and stay ahead of the key maneuvers

This is a demanding drive. With 19 significant decision points across 264.7 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: near the start: Complex interchange - multiple decisions in a short stretch; at 0.1 miles (Asbury Avenue): Lane positioning matters here; at 27.6 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here.

Critical Maneuvers

5 of 19 key points

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

0 mi into trip | ~0m in

At end of road, turn left

Complex interchange - multiple decisions in a short stretch

0.1 mi into trip | ~0m in | Asbury Avenue

Turn left onto Asbury Avenue

Lane positioning matters here

Use the left lane.

27.6 mi into trip | ~43m in | I 294 / Tri-State Tollway

Keep slight right at fork onto I 294 / Tri-State Tollway

Highway fork - watch signs carefully. Lane positioning matters here

Use the straight / slight right lanes.

29.5 mi into trip | ~45m in

Keep slight right at fork toward I 55 South: Saint Louis

Highway fork - watch signs carefully. Lane positioning matters here

Use the slight right lane. Toward I 55 South: Saint Louis

149.3 mi into trip | ~3h in | I 55

Keep slight right at fork onto I 55 toward I 55 South: Saint Louis, Springfield

Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one

Use the straight / slight right lanes. Toward I 55 South: Saint Louis, Springfield

Towns Mentioned on Route Signs

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

Between Evanston, IL and Winchester, IL, road signs point toward St. Louis and Springfield.

St. Louis

28.9 mi in | ~44m

Springfield

149.3 mi in | ~3h | via I 55

Main Roads

Road	Distance	Duration
Adlai Stevenson Expressway	119.4 mi	2h 13m
I 55	64.8 mi	1h 10m
I 72	45.4 mi	48m
Tri-State Tollway	17.5 mi	22m
West Touhy Avenue	4 mi	7m
Oakton Street	4 mi	7m
Old Route 36	3.5 mi	5m
Asbury Avenue	1 mi	1m

Longest stretch: Adlai Stevenson Expressway — 119.4 mi, about 2h 13m

Turn-by-Turn Driving Directions

Step-by-step road directions between Evanston, IL and Winchester, IL.

Start on this road

197 ft · 21 sec · this road

At end of road, turn left

139 ft · 15 sec

At end of road, turn left onto Dempster Street

213 ft · 14 sec · Dempster Street

Turn left onto Asbury Avenue

1.0 mi · 1 min · Asbury Avenue

Use the left lane.

Turn right onto Oakton Street

4.0 mi · 7 min · Oakton Street

Turn slight left onto Gross Point Road

0.5 mi · 52 sec · Gross Point Road

Turn straight onto New Gross Point Road

0.1 mi · 14 sec · New Gross Point Road

Turn right onto Howard Street

0.2 mi · 34 sec · Howard Street

Turn left onto North Lehigh Avenue

120 ft · 2 sec · North Lehigh Avenue

Turn right onto West Gross Point Road

0.9 mi · 1 min · West Gross Point Road

Turn slight right onto West Touhy Avenue

4.0 mi · 7 min · West Touhy Avenue

Use the right lane.

Turn left onto South Des Plaines River Road

184 ft · 3 sec · South Des Plaines River Road

Take the ramp

0.4 mi · 55 sec

Toward I 294 South: Indiana

Merge onto I 294

11 mi · 14 min · Tri-State Tollway

Use the straight / slight right lanes.

Keep slight left at fork onto I 294

4.8 mi · 5 min · Tri-State Tollway

Keep slight right at fork onto I 294

1.2 mi · 1 min · Tri-State Tollway

Use the straight / slight right lanes.

Take the exit

0.6 mi · 1 min

Exit 23 Toward I 55: Chicago, St. Louis

Keep slight right at fork

0.4 mi · 56 sec

Toward I 55 South: Saint Louis Use the slight right lane.

Merge onto I 55

119 mi · 2 hr 13 min · Adlai Stevenson Expressway

Use the straight / slight right lanes.

Keep slight right at fork onto I 55

65 mi · 1 hr 10 min · I 55

Toward I 55 South: Saint Louis, Springfield Use the straight / slight right lanes.

Keep slight right at fork onto I 72; US 36

45 mi · 48 min · I 72; US 36

Toward I 72 West, US 36 West: Jacksonville

Take the exit

0.4 mi · 51 sec

Toward IL 106: Winchester

Turn straight onto Old US Route 36

0.4 mi · 42 sec · Old US Route 36

Turn straight onto Old Route 36

3.5 mi · 5 min · Old Route 36

Turn left onto IL 106

0.1 mi · 15 sec · Illinois Route 106

Continue on IL 106

0.6 mi · 1 min · West Cherry Street

Arrive at destination

IL 106

Trip Plan

Morning Departure

An early start around 7-8 AM gets you there with plenty of daylight left.

Evening Departure

A late afternoon start means arriving after dark. Morning is better.

You can normally do this drive in one day.

Plan roughly 1 meaningful break for fuel, food, and rest.

The halfway point lands around 132.3 miles from Evanston, IL, or about 2h 41m into the drive.

The longest continuous stretch on this route runs about 119.4 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 80 miles or 1h 42m in

Use this first pause for coffee, a restroom break, and a quick traffic check ahead.

Halfway reset

Around 132.3 miles or 2h 41m in

This is the best place for your longest stop, a real meal, and a full fuel check.

Final approach

Final hour starts around 4h 13m

Traffic, exits, and arrival timing usually matter more near Winchester, IL than in the middle of the route.

Before You Leave

Open the route before leaving Evanston, IL 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 Evanston, IL

This is one driving day of about 264.7 miles and 5h 7m.

Your first comfortable stop window is around 80 miles from Evanston, IL.

This route can stay practical as a one-day drive if traffic stays reasonable.

Plan about 1 real break rather than only quick fuel stops.

The longest stretch is on Adlai Stevenson Expressway for about 119.4 miles.

Where to Stop

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

Halfway Point

Midpoint

About 132.3 mi from Evanston, IL · 2h 41m into the drive

Mid-route town

Meal stop

Normal, IL

132 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

Joliet, IL

Fuel and coffee

A short stop after about 80 miles helps settle the day before fatigue starts building.

Normal, IL

Meal break

The midpoint is around 132.3 miles from Evanston, IL, which is a good place for a longer meal and fuel stop.

Before the longest stretch

Fuel check

Top up before Adlai Stevenson Expressway if your tank is already low. That segment runs about 119.4 miles.

Arriving in Winchester, IL

The final approach into Winchester, IL 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 Winchester, IL.

After long uninterrupted mileage, take five minutes before the last urban segment to reset and refocus on exits, merges, and city traffic.

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

National Parks Near This Route

Worth a detour if your schedule allows.

Springfield 1908 Race Riot National Monument

National Monument

In August 1908, a large White mob attacked the Black community in Springfield, Illinois. Rioters destroyed homes and businesses and lynched two men. The event led to the founding of the National Assoc...

2 mi from route ~6 min detour Free near mile 209.9

View on nps.gov

Pullman National Historical Park

National Historical Park

In a growing Chicago neighborhood, diverse people and stories intertwined. All were seeking opportunity. Some succeeded. Others were limited—by race, gender, or economic status. Their stories came tog...

17 mi from route ~42 min detour Free near mile 27.4

View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

Fuel & Cost

Regular Gas

$41.38 one way

$82.77 round trip

$3.97/gal 25.4 MPG avg 93 kg CO₂

Fuel Type	$/gal	One Way	Round Trip
midgrade	$4.36	$45.44	$90.87
premium	$4.89	$50.94	$101.88
diesel	$5.61	$58.44	$116.88

Estimated Tolls: $1.05

Tri-state Tollway (17.5 mi) $1.05

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

Estimated Trip Cost (one way, 1 person)

Fuel

$41

Tolls

Meals

$25–$50

Total

$67–$92

Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.

Estimated CO2 emission: 92.6 kg one way. Prices: EIA weekly data, 2026-04-13.

EV Charging Along Route

15 DC fast chargers · Coverage: excellent

Village Crossing - Tesla Supercharger

Skokie, IL

Tesla

20 DCFC

1800 Maple Self Park Garage - Tesla Supercharger

Evanston, IL

Tesla

12 DCFC

Abt Electronics - Tesla Supercharger

Glenview, IL

Tesla

10 DCFC

Westfield Old Orchard (Skokie, IL)

Skokie, IL

Electrify America

6 DCFC

Golf Mill Ford

Niles, IL

EVXY

6 DCFC

Whole Foods Sauganash (CIC)

Chicago, IL

eVgo Network

4 DCFC

Crosby's Kitchen Niles (GFCS LLC)

Niles, IL

IN_CHARGE

4 DCFC

Golf Mill Chevrolet

Niles, IL

EVXY

4 DCFC

Tesla: 4 Electrify America: 2 eVgo Network: 2 EVXY: 2 EV Connect: 1 Non-Networked: 1 ChargePoint Network: 1 IN_CHARGE: 1 Blink Network: 1

Station data from NREL Alternative Fuel Stations database.

Driving Electric?

About $28 in charging · 0 stops · 67% less CO₂

Vehicle Type	kWh	Stops	DC Fast	Home Charge
Average EV	79.4	0	$27.79	$12.71
Efficient EV	66.2	0	$23.16	$10.59
EV Truck/SUV	105.9	1	$37.06	$16.94

Gas CO2

93 kg

EV CO2

31 kg (67% less)

Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.

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 data refreshed 4 days ago

Origin

Evanston, IL

Night in Evanston on Tuesday

Local time

9:00 PM

CDT

Current temp

50°F

Unavailable

Live forecast

Destination

Winchester, IL

Night in Winchester on Tuesday

Local time

9:00 PM

CDT

Current temp

55°F

Unavailable

Live forecast

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

5 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

5h 7m on the road

An early start around 7-8 AM gets you there with plenty of daylight left.

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

Frequently Asked Questions

The drive from Evanston, IL to Winchester, IL covers 264.7 miles and takes about 5h 7m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are Adlai Stevenson Expressway, I 55, I 72. Most of the drive stays on highways, so watch for ramps and exits.

This is a comfortable same-day trip.

The midpoint is about 132.3 miles from Evanston, IL. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $41.38 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

An early start around 7-8 AM gets you there with plenty of daylight left. A late afternoon start means arriving after dark. Morning is better.

Plan about 1 meaningful break for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.

Between Evanston, IL and Winchester, IL, road signs point toward St. Louis and Springfield.

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