5 Places Near Chicago That Make for the Perfect Weekend Getaway

Whether you’re from Chicago or just visiting, you’ll want to check out the adorable places!

The birthplace of the skyscraper is home to many award-winning restaurants, some of the top sports teams, and numerous prized cultural treasures.

But we all need a break every once in a while to get away from the excitement of our country’s third-largest city, and there is a myriad of getaways within easy driving distance.

While you can explore the rural part of Illinois, you can also enjoy neighboring Wisconsin, Michigan, Indiana, or Iowa, all within one weekend.

So whether you wish to plan some kind of romantic getaway with your significant other to a charming small-town bed-and-breakfast or a family-friendly trip to explore nature, these 5 Midwest destinations near Chicago will shed the stress of big-city living.

Click “Next” To See The Charming Locations!

Galena, Illinois

Driving time from Chicago: 3 Hours

If you start driving northwest of Chicago, you’ll reach the charming small town of Galena. It’s a small area behind the Mississippi River that’s wrapped in Italian-style buildings every which way you look.

Galena has been triumphant in preserving the heritage of the 19th century, and you can see it through its architecture. You can get a perfect scenic view of the hilly terrain by taking an enormous hot air balloon ride in the sky.

And while here, take a stroll to visit several quaint churches, some fantastic antique shops, and enjoy the delicious dining to spend a few great moments with your loved ones.

Spring Green, Wisconsin

Driving time from Chicago: 3.5 Hours

Peaceful and charming, we understand why the picturesque village of Spring Green, located on the Wisconsin River, drew in Frank Lloyd Wright, who built his summer home, Taliesin, here.

And while that’s definitely worth a visit, we suggest you head to the House on the Rock, an interesting wonderland of knick-knacks and artifacts that’s set literally on a massive rock, surrounded by dramatic views of the beautiful towering trees.

While there, make sure you don’t miss the enormous indoor carousel or the Infinity Room, an engineering wonder with 3,264 windows that extend 218 feet over the valley.

And if you’re searching for a place to stay, you can step back in time at Spring Valley Inn, which was designed by the Frank Lloyd Wright School of Architecture.

The tiny inn on the wooded prairie will give you unbeatable views of the valley. It also doesn’t hurt that it has a fire pit, relaxing bar, patio, hot tub, indoor pool, and workout room.

Lake Geneva, Wisconsin

Driving time from Chicago: 1.5 Hours

This resort city makes Lake Geneva an idyllic weekend getaway close to Chicago. The area is known as the “Newport of the Midwest” because of its lakefront mansions.

In fact, you can catch a glimpse of these impressive homes by strolling along the Geneva Lakeshore Path. It’s a rustic 25-mile walkway encircling the lake, winding right through the backyards of the magnificent estates.

Surprisingly, you won’t see any “No Trespassing” signs to scare you away, either. Just be aware that the path isn’t built for rollerblades or bikes since you’ll have to maneuver steps and other minor obstacles.

After your stroll, a lakefront cruise is another delightful way to enjoy this city. Visitors have given Lake Geneva Cruise Line fantastic reviews for being informative while also entertaining.

Various daily sails are available, of which the most unique is the mail delivery cruise. This area, not far from Chicago, is one of the only remaining places in the US where mail still gets delivered by boat.

About 75 lakefront homes get their US mail service this way, and passengers can go along for the ride!

Saugatuck, Michigan

Driving time from Chicago: 2.5 Hours

Nicknamed the Art Coast of the state, this trendy resort town that’s a mere two-and-a-half-hour drive away from Chicago is chock-full of boutiques, galleries, incredible dining options, and beaches.

Grab a seat at the counter of the 100-year-old Saugatuck Drug Store, and you’ll get a feel of the town’s more traditional side that’s served up through a classic ice cream soda or malt.

You’ll be in for another nostalgia trip when you hop aboard the chain ferry: Operating since 1838, it proclaims to be the only remaining chain-driven ferry in our country, ferrying passengers across the Kalamazoo River between downtown and Oval Beach.

After dismounting on Oval Beach, beachgoers climb the 300-plus steps to the top of Mount Baldhead and get a bird’s eye view of the location.

Turkey Run State Park, Indiana

Driving time from Chicago: 3.5 Hours

Turkey Run State Park is one of Hoosier State’s oldest and most popular state parks and it happens to be the crown jewel of Parke County.

Eleven trails that range from half a mile to 2 miles spiral through rugged ravines encircled by the park’s signature sandstone cliffs, presenting you with Midwest hiking at its best.

If you choose to spend the night, Turkey Run Inn, a popular option that’s situated in the park, is valued by guests for its friendly staff and warm atmosphere.

They have an indoor pool and lots of public sitting areas that include fireplaces if you want to sit back and read a book or play a relaxing board game. And you can either choose the rooms within the historic lodge or stay in one of the adjacent cabins.

The Narrows, the Inn’s restaurant, is also popular among visitors for its catfish dinners, fried biscuits, and hot apple butter.

Now that we’ve shared some of our favorite places with you near Chicago be sure to tell us about YOUR favorite places in the comments below!

And if you enjoyed reading this, we also recommend you check out: 5 Charming Small Towns Within a 2-hour Drive of Big Cities