Day Trips from Waukegan
← All Waukegan day tripsDay Trips from Waukegan: Scenic Drives & Road Trips
The most beautiful scenic drives and road trip routes within reach of Waukegan, IL. Winding back roads, dramatic overlooks, and picture-perfect byways that make the drive itself the destination. Drive times and route info included.
12 scenic drives near Waukegan
Portage Dune Overlook
Portage, IN 46368
Just 1 hr 36 min from Waukegan, rated 5.0 stars, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Oak Ridge Overlook
Lisle, IL 60532
Just 60 min from Waukegan, rated 5.0 stars, perfect for hiking, scenic views, and getting outdoors.
Best time to visit: Spring through fall for trails and foliage. Fall colors peak mid-October.
Kettle Moraine Scenic Drive
West Bend, WI 53090
Just 1 hr 29 min from Waukegan, rated 4.9 stars, packed with outdoor activities and adventure.
Best time to visit: Spring through fall for most outdoor activities. Winter for snow sports where available.
Scenic overlook
Whitewater, WI 53190
Just 1 hr 21 min from Waukegan, rated 4.9 stars, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Start of Rustic Road 29
Lake Geneva, WI 53147
Just 59 min from Waukegan, rated 4.9 stars, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Scenic overlook
Galena, IL 61036
Just 2 hrs 43 min from Waukegan, rated 4.9 stars, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Kiesel Viewing Structure
St Joseph, MI 49085
Just 2 hrs 20 min from Waukegan, rated 4.8 stars, perfect for hiking, scenic views, and getting outdoors.
Best time to visit: Spring through fall for trails and foliage. Fall colors peak mid-October.
Castle Rock Overlook
Oregon, IL 61061
Just 2 hrs 8 min from Waukegan, rated 4.8 stars by 329 visitors, packed with outdoor activities and adventure.
Best time to visit: Spring through fall for most outdoor activities. Winter for snow sports where available.
Montrose Moonrise Observation Point One
Chicago, IL 60613
Just 1 hr 4 min from Waukegan, rated 4.8 stars by 170 visitors, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
North End of Kettle Moraine Scenic Drive
Plymouth, WI 53073
Just 1 hr 57 min from Waukegan, rated 4.8 stars, packed with outdoor activities and adventure.
Best time to visit: Spring through fall for most outdoor activities. Winter for snow sports where available.
Scenic Overlook and Rest Area
Gary, IN 46403
Just 1 hr 34 min from Waukegan, rated 4.7 stars, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Greene Valley Scenic Overlook
IL 60440, USA
Just 1 hr 5 min from Waukegan, rated 4.7 stars, perfect for hiking, scenic views, and getting outdoors.
Best time to visit: Spring through fall for trails and foliage. Fall colors peak mid-October.
Frequently Asked Questions About Scenic Drives Day Trips from Waukegan
What are the best scenic drives near Waukegan, IL?
The best scenic drives near Waukegan include national scenic byways, state route back roads, and lakefront highways with dramatic views. Check the destinations above for top-rated scenic stops along these routes.
How long are the scenic drives from Waukegan?
Most scenic drives near Waukegan range from 1-4 hours one way. Many can be done as a loop or combined with stops for hiking, dining, or small-town exploring to fill a full day.
What is the best time of year for scenic drives near Waukegan?
Fall (mid-September through October) is peak season for scenic drives near Waukegan, with spectacular foliage. Spring wildflower season and summer green are also beautiful. Winter drives can be dramatic but check road conditions first.
What should I bring on a scenic drive from Waukegan?
Bring a full tank of gas, snacks, water, and a camera. Cell service is unreliable on many scenic routes, so download maps beforehand. Pack layers since temperatures at overlooks can be cooler than in the city.
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