The 8 best scenic drives near Chicago

As the largest city in the Midwest, Chicago offers many avenues to get out and explore both in the city’s unique neighborhoods and in the surrounding areas. Here are our top 8 ideas for scenic drives in and around Chicago. 

1. Logan Square Boulevards District

Located on the north side of Chicago, the Logan Square Boulevards District, comprised of Logan, Kedzie, Palmer and Humboldt boulevards, is a part of Chicago’s historic district. It’s a beautiful area filled with late 19th-century and early 20th-century buildings, monuments and architecture that are likely to inspire you to get out and take a few pictures. If you do, check out the Illinois Centennial Monument, which was built in 1918 to celebrate Chicago’s 100th birthday.  

2. Lake Shore Drive

Both Chicagoans and travelers alike love to cruise along Lake Shore Drive because of its seemingly endless views of Lake Michigan. If the weather is nice, park your car and walk along the beach. Lake Shore Drive is truly Chicago at its best.

3. Humboldt Park

Located inside Humboldt Park, Luis Munoz Marin Drive and N Humboldt Drive offer a nice scenic route on Chicago’s west side. Not only is the park beautiful and lush, but the surrounding buildings have magazine-worthy architecture. You’ll find numerous spots you’ll want to pull over and explore, from neighborhood restaurants and shops to idyllic streets. Once you’ve scoped out the area, find a place to get out of your car and walk around in the park. It has many features to enjoy, including a boat house, lagoon, lots of green space and the National Museum of Puerto Rican Arts & Culture.

4. Wells Street Bridge

While driving across it will only take a few moments, the Wells Street Bridge, connecting the River North and Loop neighborhoods, is one of the most iconic bridges in Chicago. It is an engineering marvel in that it is both a movable bridge and a bridge that carries the CTA trains. To the east and west, you’ll see beautiful views of downtown Chicago and the glittering Chicago River. If you can find a place to park, head to the bridge on foot to really take in the views. 

5. The Morton Arboretum

Distance from Chicago: 28 miles (40 minutes)

At just over nine miles, the road inside the Morton Arboretum is a great place to go for a quick scenic drive. For a longer visit, pack a picnic and find a spot to soak in the greenery of the arboretum, or follow one of the numerous trails to explore the area and get a closer view of its famed gardens and statues.

6. Starved Rock State Park

Distance from Chicago: 95 miles (1 hour and 45 minutes)

Starved Rock State Park features numerous bluffs and canyons that were created by glacial drifts approximately 300,000 years ago. Beautiful waterfalls develop among the canyons when it rains, and you’re likely to see an eagle or two hunting along the water. For a longer drive, try coupling your Starved Rock trip with a scenic route along the nearby Illinois River.  

7. Grandview Drive

Distance from Chicago: 155 miles (2 hours and 45 minutes)

Although Grandview Drive won’t take you very long to explore, it’s one of the most scenic drives in Illinois. At 2.52 miles long, it’s surrounded by almost-panoramic views of the Illinois River Valley. In fact, President Theodore Roosevelt once stated it was the “world’s most beautiful drive.” On a clear day, find a place to pull over and take in the view of nearly 30 miles of visibility over the water. 

8. Door County, WI

Distance from Chicago: 272 miles (4 hours and 20 minutes)

If you have a few extra days built into your Chicago trip, consider a visit to Door County. It’s around 4 hours away, but stretches of the drive take you along the scenic Lake Michigan shoreline. In addition to charming small towns, you’ll also pass through Milwaukee and Green Bay, Wisconsin, which have many beautiful views and attractions to enjoy. The Door County peninsula is a popular getaway with numerous beaches, state parks and outdoor activities that can be enjoyed any time of year. 

Chicago driving trip tips

When you’re preparing to drive around Chicago, remember our tips for a smooth trip.

Check your tires

Check the tire pressure of each tire to make sure it’s at the correct level. Consult your owner’s manual for the ideal pressure, and then use a gauge or drive over to the gas station to see if you need to add air.

Keep water and snacks on hand

No one likes to think about a worst-case scenario, but planning for it is smart. If your car happens to break down during your drive or you get stranded somehow, you don’t want to worry about getting hungry or dehydrated. Always keep bottled water and snacks in the car just in case.

Explore Chicago with Avail

Ready for a scenic drive near Chicago? When you borrow a car with Avail, you can choose the right vehicle for your trip, like a spacious SUV, so everyone can ride comfortably. Avail offers affordable daily rates, insurance coverage from Allstate, 24/7 roadside assistance and a free second driver, so you can get on your way stress-free and share driving responsibilities without a care.