Waukegan to Montgomery is 69.6 miles and takes about 1h 33m via Tri-State Tollway and Ronald Reagan Memorial Tollway, with a fuel budget near $11 and enough daylight to finish in a day. This trip stays within Illinois, traversing the Midwest region on a mix of tollways and surface streets. Given the relatively short duration, this route is well-suited for a single-day excursion. The majority of the drive involves navigating established toll roads before transitioning to local routes closer to your destination. Plan for a straightforward trip with minimal detours.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
34.8 miles from Waukegan, IL
A natural place for your longest stop of the day
, about 45m into the drive
.
Main Roads
Road
Distance
Duration
Tri-State Tollway
35.5 mi
44m
Ronald Reagan Memorial Tollway
22.8 mi
27m
North Lake Street
4.7 mi
9m
Belvidere Road
2.2 mi
3m
Belvidere Street
1.6 mi
3m
North Jackson Street
0.5 mi
1m
Glen Rock Avenue
0.5 mi
1m
South Lincolnway Street
0.4 mi
<1m
Longest stretch:
Tri-State Tollway
— 35.5 mi, about 44m
Turn-by-Turn Driving Directions
Step-by-step road directions between Waukegan, IL and Montgomery, IL.
1
Start on North Jackson Street
0.5 mi·1 min·North Jackson Street
2
Turn right onto Glen Rock Avenue
0.5 mi·1 min·Glen Rock Avenue
3
Turn right onto Belvidere Street
1.6 mi·3 min·Belvidere Street
4
Continue on IL 120
2.2 mi·3 min·Belvidere Road
Use the straight / right lanes.
5
Take the ramp
0.3 mi·37 sec
Toward I 94 East Toll: Chicago
6
Merge onto I 94
14 mi·15 min·Tri-State Tollway
Use the straight / slight right lanes.
7
Keep slight right at fork onto I 294
20 mi·25 min·Tri-State Tollway
Toward I 294 South Toll: Indiana, O'HareUse the slight right lane.
8
Take the exit onto I 294
1.0 mi·1 min·Tri-State Tollway
Toward I 88 West, I 294 South: Aurora, IndianaUse the slight right lane.
9
Keep slight right at fork onto I 294
0.2 mi·30 sec·Tri-State Tollway
Toward I 88 West, I 294 South: Aurora, IndianaUse the slight right lane.
10
Continue on I 294
0.4 mi·47 sec·Tri-State Tollway
Exit 15AToward I 88 West, I 294 South: Aurora, Indiana
11
Keep slight right at fork
0.5 mi·49 sec
Exit 31AToward I 88 West Toll: AuroraUse the straight / slight right lanes.
12
Merge onto I 88; IL 110
0.8 mi·59 sec·Ronald Reagan Memorial Tollway
13
Keep slight right at fork onto I 88; IL 110
22 mi·26 min·Ronald Reagan Memorial Tollway
Exit 138Toward 22nd Street (Cermak Road)Use the slight right lane.
14
Take the exit
0.6 mi·1 min
Exit 117Toward IL 31, IL 56 EastUse the right lane.
15
Turn right onto IL 31
0.4 mi·52 sec·South Lincolnway Street
16
Continue on IL 31
4.7 mi·9 min·North Lake Street
17
Arrive at destination
IL 31
Trip Plan
Given the 1h 33m duration and 69.6-mile distance, this is an easy same-day trip. Leaving in the morning or early afternoon will give you plenty of time to reach Montgomery without feeling rushed. Since there are no designated stops and the drive is under 2 hours, you likely won't need to break it up. However, if you prefer a more leisurely pace, consider a brief stop around the halfway mark. Keep an eye on your fuel gauge, as the estimated cost is $11, and topping off before you leave Waukegan is a good idea.
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 34.8 miles from Waukegan, IL, or about 45m into the drive.
The longest continuous stretch on this route runs about 35.5 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 15 miles or 20m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 34.8 miles or 45m 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 16m
Traffic, exits, and arrival timing usually matter more near Montgomery, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Waukegan, IL so your first major turns are already loaded.
Day 1
Settle into the route from Waukegan, IL
This is one driving day of about 69.6 miles and 1h 33m.
Your first comfortable stop window is around 15 miles from Waukegan, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Tri-State Tollway for about 35.5 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 12
5 decision points cluster between mile 18.9 and 63.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
18.9 mi into trip|~25m in|I 294 / Tri-State Tollway
Keep slight right at fork onto I 294 / Tri-State Tollway toward I 294 South Toll: Indiana, O'Hare
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 294 South Toll: Indiana, O'Hare
8
40 mi into trip|~52m in|I 294 / Tri-State Tollway
Keep slight right at fork onto I 294 / Tri-State Tollway toward I 88 West, I 294 South: Aurora, Indiana
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 88 West, I 294 South: Aurora, Indiana
8
40.6 mi into trip|~54m in
Keep slight right at fork toward I 88 West Toll: Aurora
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Exit 31A
Toward I 88 West Toll: Aurora
8
41.8 mi into trip|~55m in|I 88; IL 110 / Ronald Reagan Memorial Tollway
Keep slight right at fork onto I 88; IL 110 / Ronald Reagan Memorial Tollway toward 22nd Street (Cermak Road)
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 138
Toward 22nd Street (Cermak Road)
8
63.9 mi into trip|~1h 22m in
Take the exit toward IL 31, IL 56 East
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Exit 117
Toward IL 31, IL 56 East
Fuel & Cost
Regular Gas
$10.88 one way
$21.76 round trip
$3.97/gal25.4 MPG avg24 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.36
$11.95
$23.89
premium
$4.89
$13.39
$26.79
diesel
$5.61
$15.37
$30.73
Estimated Tolls: $3.50
Tri-state Tollway
(35.5 mi)$2.13
Reagan Memorial Tollway
(22.8 mi)$1.37
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
$11
Tolls
$4
Meals
$25–$50
Total
$39–$64
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 24.4 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $7 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
20.9
0
$7.31
$3.34
Efficient EV
17.4
0
$6.09
$2.78
EV Truck/SUV
27.8
0
$9.74
$4.45
Gas CO2
24 kg
EV CO2
8 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 20, 2026
Origin
Waukegan, IL
Morning
in Waukegan on Tuesday
Local time
10:07 AM
CDT
Current temp
58°F
Unavailable
Live forecast
Destination
Montgomery, IL
Morning
in Montgomery on Tuesday
Local time
10:07 AM
CDT
Current temp
65°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
7 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
1h 33m 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.
National Parks Near This Route
Worth a detour if your schedule allows.
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...
20 mi from route
~50 min detour
Free
near mile 40.8
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive is predominantly surface roads, with 0% highway share. You'll encounter a longest stretch of 35.5 miles on the Tri-State Tollway. After exiting the tollways, the route shifts to local streets like North Lake Street, offering a different driving experience. Expect to navigate through more developed areas with frequent intersections as you approach Montgomery.
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: 35.5 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 around 18.9 miles in near I 294 / Tri-State Tollway.
Driving Effort9/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 69.6 miles you will encounter 12 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 18.9 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 40 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 40.6 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Waukegan, IL and Montgomery, IL, road signs point toward O'hare, Indiana and 22Nd Street (Cermak Road).
Waukegan is in the Far North Suburbs of the Chicagoland region of Illinois. It sits on Lake Michigan, has a large harbor, and is the county seat of Lake County, Illinois.
Doable as a same-day drive at 1h 33m. Total distance: 69.6 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 33m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 35.5 miles on Tri-State Tollway. The full list of main roads is in the Roads section above.
Expect about $3.50 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.
Yes — we found about 2 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
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 Montgomery, 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: at 18.9 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 40 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 40.6 miles: Highway fork - watch signs carefully. Lane positioning matters here.
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 Montgomery, IL before heading back.
