Chicago is a great city to live in or visit, but sometimes you just need a change of scenery. We’ve been to Chicago plenty of times and wrote a few posts about it, including this post. Luckily, there are many amazing destinations within a few hours’ drive from the Windy City that offer stunning views, rich culture, and fun activities. Whether you’re looking for a relaxing getaway, an adventurous escape, or a historical exploration, you’ll find it on one of these road trips near Chicago.

In this post, I’ll share with you some of the most beautiful road trips near Chicago that I’ve personally taken and enjoyed. I’ll also give you some tips on what to see, do, and eat along the way, as well as the pros and cons of each trip. So buckle up and get ready for a ride!

However, before we embark on our journey – you should be aware that driving on a long road trip can often feel like a routine task. However, the road is unpredictable, and the difference between a close call and a collision can often be a matter of seconds and smart decisions. According to car accident lawyers at Briskman Briskman & Greenberg in Chicago, car accidents can lead to many injuries, from minor bumps and bruises to severe injuries to the brain and head, and even death. Therefore, defensive driving on any sort of road trio is crucial for staying safe on the roads. 

And now – without further ado – my favorite road trips near Chicago…

Starved Rock State Park

Distance: 100 miles Drive Time: 2 hours Where to Stay: Starved Rock Lodge & Conference Center

If you’re craving some nature and hiking, Starved Rock State Park is the perfect place to go. Located along the Illinois River, this park features 18 canyons, 13 miles of trails, and numerous waterfalls. You can explore the sandstone bluffs, the lush forests, and the scenic overlooks that make this park a natural wonder.

Some of the highlights of Starved Rock State Park include:

  • The Lover’s Leap Overlook, which offers a panoramic view of the river and the park. Legend has it that two Native American lovers jumped from this spot to their deaths rather than be separated by their warring tribes.
  • The St. Louis Canyon, which has a 80-foot waterfall that freezes in the winter, creating a spectacular ice sculpture.
  • The Wildcat Canyon, which has the largest waterfall in the park and a narrow gorge that creates a natural amphitheater.

Watch this video to get a glimpse:

The pros of this road trip are:

  • It’s a short and easy drive from Chicago, with no tolls or traffic.
  • It’s a great way to enjoy the outdoors and get some exercise, especially in the fall when the leaves change colors.
  • It’s free to enter the park and there are plenty of picnic areas, restrooms, and parking spots.

The cons of this road trip are:

  • It can get crowded on weekends and holidays, so you may have to wait for a parking spot or a trail.
  • It can get buggy and muddy in the summer, so bring insect repellent and appropriate footwear.
  • It can get cold and snowy in the winter, so check the weather and trail conditions before you go.


Distance: 92 miles Drive Time: 1.5 hours Where to Stay: The Pfister Hotel

If you’re looking for a city break with a different vibe, Milwaukee is a great option. This city on the shores of Lake Michigan has a lot to offer, from culture and history to beer and cheese. You can experience the best of Milwaukee in a day or two, or stay longer and explore the surrounding areas.

Some of the highlights of Milwaukee include:

  • The Milwaukee Art Museum, which has a stunning collection of over 25,000 works of art, as well as a futuristic building with a moving “wings” that open and close.
  • The Harley-Davidson Museum, which showcases the history and culture of the iconic motorcycle brand, as well as hundreds of bikes, memorabilia, and interactive exhibits.
  • The Milwaukee Public Market, which is a food lover’s paradise, with over 20 vendors selling fresh produce, baked goods, cheese, meat, seafood, and more.

Watch this video to get a glimpse:

The pros of this road trip are:

  • It’s a quick and scenic drive from Chicago, along the lakefront and through charming towns.
  • It’s a fun and friendly city, with a lot of diversity, creativity, and charm.
  • It’s a beer lover’s dream, with dozens of breweries, pubs, and festivals to choose from.

The cons of this road trip are:

  • It can get cold and windy in the winter, so dress warmly and be prepared for snow.
  • It can get expensive, especially if you stay at a downtown hotel or eat at a fancy restaurant.
  • It can get boring, if you’re not into art, history, or beer.


Distance: 165 miles Drive Time: 3 hours Where to Stay: Jail Hill Inn

If you’re looking for a charming and historic town with a lot of character, Galena is a great choice. This former mining town in northwest Illinois has preserved its 19th-century architecture and offers a variety of attractions, shops, and restaurants. You can stroll along the Main Street, visit the Ulysses S. Grant Home, or take a trolley tour of the town.

Some of the highlights of Galena include:

  • The Galena Cellars Vineyard & Winery, which produces over 40 award-winning wines and offers tastings, tours, and events.
  • The Chestnut Mountain Resort, which is a year-round destination for skiing, snowboarding, ziplining, alpine sliding, and scenic views of the Mississippi River.
  • The Galena Ghost Tours, which take you to the most haunted places in town and tell you spooky stories and legends.

Watch this video to learn more:

The pros of this road trip are:

  • It’s a scenic and relaxing drive from Chicago, with rolling hills and farmlands.
  • It’s a quaint and cozy town, with a lot of history, culture, and charm.
  • It’s a romantic and peaceful getaway, with many bed and breakfasts, spas, and candlelit dinners.

The cons of this road trip are:

  • It can get crowded and touristy on weekends and holidays, so you may have to book in advance or pay higher prices.
  • It can get hot and humid in the summer, so bring sunscreen and water.
  • It can get boring, if you’re not into history, wine, or antiques.

To Conclude…

These are just some of the most beautiful road trips near Chicago that you can take to enjoy a different scenery and experience. Whether you’re into nature, culture, history, or adventure, you’ll find a destination that suits your taste and budget. So what are you waiting for? Pack your bags, grab your keys, and hit the road!

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“The Jaded Traveler”. Ron Rossi was born and raised in New York. A globalist at heart, Ron is a marketing director by trade, and has lived and worked around the world including Asia, Europe, Africa, and South America. Food is one of the best ways to learn about a country, a people and a culture. So, Ron is always looking for the best in mid-range to budget and street food. He is always on the hunt for a good meal anyone can afford. It is the food of the average citizen that excites him. And with having visited close to 100 countries on 6 continents so far, there have been some pretty good meals.