Best Weekend Getaways From Chicago

With iconic sights and architecture, numerous museums, and plenty of world-renowned fine dining options, Chicago is a city like no other. That being said, it’s always nice to temporarily escape the hustle of the bustle of the city and visit charming nearby small towns, and natural wonders.

Here is our list of the perfect road trips and weekend getaways for when you need to escape Chicago.

Sleeping Bear Dunes National Lakeshore with views of Lake Michigan.

Traverse City, Michigan

323 miles northeast, 5-hour drive

Home to 35 miles of scenic coastline, beautiful freshwater beaches, dunes, an extensive trail network, vineyards, a National Lakeshore, and numerous lush green forests, Traverse City is undoubtedly one of the most gorgeous locations in the Midwest. Visit the nearby Sleeping Bear Dunes National Lakeshore and relax on its beautiful deep blue water beaches. Or head on over one of the over 10+ vineyards on Old Mission Peninsula and enjoy some great wine with breathtaking views of Grand Traverse Bay and Lake Michigan. 

Love the outdoors? With scenic paved and dirt trails all over the region, Traverse City is the perfect hiking and biking destination. And due to its location on Grand Traverse Bay, near freshwater lakes, streams, and rivers, Traverse City has an abundance of watersport options as well. Whatever your hobbies, Traverse City has something to offer for everyone. Be sure to book your stay at Delamar Traverse City – our newest waterfront location that offers exquisite views of Grand Traverse Bay, a fine dining restaurant, as well as boat charters & cruise excursions. 

Lake Geneva, Wisconsin

80 miles northwest, 1.5-hour drive

Lake Geneva has been Chicago’s number one vacation destination for decades. This lake town is home to beautiful beaches, and an array of outdoor activities, including lake cruises, hot air balloon rides, hiking, paddleboarding, a safari park, and zip-lining. Its charming downtown is home to several one-of-a-kind designer and independent boutiques, as well as numerous cafes, ice cream parlors, and local eateries. 

During the winter months, visitors can enjoy snow skiing & tubing at multiple terrain parks, as well as cross-country skiing at one of the area’s many trails. 

Starved Rock State Park – Illinois

Starved Rock State Park, Illinois

90 miles southwest, 1.5-hour drive

Home to 13 miles of trails and 18 canyons, Starved Rock State Park is a must-visit Illinois gem. Beautiful, seasonal waterfalls can be seen in the spring and after heavy rains. Visitors can hike to the seasonal waterfalls and sandstone canyons. You can also explore the Illinois River by boat and enjoy some fishing amongst nature. 

The park has 133 premium campsites complete with electricity and bathhouses for visitors to enjoy and explore the park’s scenic beauty.  

Saugatuck & Douglas, Michigan

139 miles northeast, 2.5-hour drive

Home to award-winning pristine beaches, scenic waterways, and dunes, Saugatuck/Douglas offers the ultimate recreation and relaxation escape. Visitors can kick back and relax along the 10 miles of prime Lake Michigan beaches, or hit the waters on kayaks, sailboats, and paddleboards. 

The area is known as “the art coast of Michigan,” and is home to a thriving art scene and dozens of art galleries that line the charming downtown district. It is also one of the most LGBTQ+ friendly small resort towns in America and home to dozens of LGBTQ-owned businesses. 

Galena, Illinois

164 miles northwest, 3-hour drive

With gorgeous cobblestone streets amidst carefully preserved nineteenth-century buildings, historic mansions, and scenic rolling hills, Galena is a charming riverside destination for history buffs. More than 85 percent of the town (over 1,000 buildings, including the home of Ulysses S. Grant, the 18th president of the United States) is listed on the National Register of Historic Places. The beautiful downtown area is home to more than 100 storefronts featuring clothing, jewelry, collectibles, and specialty items, as well as, local eateries for visitors to explore. You can also find four vineyards with award-winning, estate-grown wines in the area. 

Beyond Downtown, visitors can find plenty of water sports, golf, and other active outings, including rafting trips along the Mississippi River, and skiing. 

Milwaukee, Wisconsin

93 miles north, 1.5-hour drive

Whether you want to visit a museum, take a boat tour on Lake Michigan, or explore free art, Milwaukee has something for everyone. You can also stroll along the two-mile long RiverWalk by the Milwaukee River to stop at one of many great restaurants or brew pubs along the way. Milwaukee is known as the original Brew City, and is home to several iconic beer brands from a variety of brewers, including Blatz, Pabst, Schlitz and Miller. The city is also home to the Harley-Davidson Museum, with a 20-acre, park-like campus, and a calendar full of activities for motorcycle lovers.