The holidays are winding down, and a vacation from the vacation is much needed for many! If you live in Chicago, you’re in luck. The Windy City is ideally located near great weekend getaways, including historic towns, national parks, lakeside retreats, and much more.

Here are a few of our favorite weekend getaways from Chicago:

1. Milwaukee, Wisconsin: A Brew City Gem

Distance from Chicago: Approximately 90 miles

Why go: Explore the Milwaukee Art Museum, visit the Harley-Davidson Museum, and enjoy the city’s vibrant food and craft beer scene.

If you’re a beer person, Milwaukee is for you. Home to the Miller Brewing Company, visitors can schedule a tour to learn about the beer-making process and taste the brews that made Miller a household name. In addition to Miller, there are tons of other craft breweries scattered throughout the city that are also must-visits.

Milwaukee isn’t just about beer, however. Stroll along the scenic RiverWalk, explore the historic Third Ward, and book a reservation at one of the city’s renowned restaurants. The Milwaukee Art Museum is a must-see if you’re into art, and the Harley-Davidson Museum is ideal for motorcycle enthusiasts. You will have the opportunity to explore an extensive collection of vintage motorcycles and interact with exhibits that celebrate the Harley-Davidson brand.

2. Galena, Illinois: A Step Back in Time

Distance from Chicago: Approximately 164 miles

Why go: A charming historic town with 19th-century architecture, boutique shops, and outdoor activities such as hiking and hot air balloon rides.

Nestled along the Galena River, Galena is a living museum of 19th-century architecture. Walking along the town streets of this historic mining town truly feels like you have stepped back in time. Lined with cobblestone streets and well-preserved buildings, Galena offers historic bed and breakfasts and beautiful river walks along the Galena River. Take a hot air balloon to see this beautiful town from above or hike the scenic trails of the nearby Galena River Trail.

The buildings in Galena have been painstakingly preserved, with 85% of them on the National Register of Historic Places. While in Galena, be sure to tour the Ulysses S. Grant Home State Historic Site. This residence was gifted to Ulysses S. Grant in 1865 by Galena citizens.

3. Lake Geneva, Wisconsin: Lakeside Bliss

Distance from Chicago: Approximately 80 miles

Why go: Relax by the lake, take a boat tour, explore the charming downtown, and visit the historic Black Point Estate.

Lake Geneva is a Wisconsin resort city that offers the perfect weekend getaway or day trip. Walk along the Geneva Lakeshore Path and stroll through the backyards of Lake Geneva’s stunning lakefront mansions. You won’t see any “No Trespassing” signs, but you may see signs that some paths aren’t for strollers/bikers, so be cautious when touring the mansions.

The crystal-clear waters of the lake provide the perfect backdrop for boat tours, water sports, and lakeside picnics. Lake Geneva is one of the only remaining places in the United States with mail delivered by boat, and visitors can book a mail delivery cruise to learn more about this unique process.

A serene waterfall cascading into a tranquil pool within a forested canyon.
Nature’s Symphony: Dive into the serenity of Starved Rock State Park near Chicago, where cascading waterfalls offer a refreshing escape amidst picturesque canyons.

4. Starved Rock State Park, Illinois: Nature’s Playground

Distance from Chicago: Approximately 94 miles

Why go: Hike through scenic canyons, and waterfalls, bike, kayak, or cross-country ski in one of Illinois’ most beautiful state parks.

If you’re into hiking, Starved Rock State Park is the place for you. Located along the Illinois River, this is an ideal day trip from Chicago. Bike, hike, or enjoy cross-country skiing in this gorgeous state park. The park boasts over 13 miles of well-maintained trails suitable for hiking at all levels, from beginner to advanced. Trails will take you to towering canyons, cascading waterfalls, and panoramic views of the Illinois River.

If hiking isn’t for you or you want to take a break, rent a kayak and go paddling along the Illinois River. After a day of hiking, biking, kayaking, or cross-country skiing, spend a relaxing evening enjoying a scenic riverboat cruise or stay at the historic Starved Rock Lodge.

5. Michigan City, Indiana: Beachlover’s Paradise

Distance from Chicago: Approximately 50 miles

Why go: Visit the Indiana Dunes National Park, explore the outlet mall, and relax on the beaches of Lake Michigan.

Michigan City in Indiana offers a diverse array of attractions, including the Indiana Dunes National Park. Indiana Dunes National Park is a haven for beach lovers and hikers with its sandy shores and towering dunes.

After spending the day at the national park, splurge at the Lighthouse Place Premium Outlets or explore the historic Washington Park.

6. Grand Rapids, Michigan: A City of Art and Culture

Distance from Chicago: Approximately 180 miles

Why go: Visit the Gerald R. Ford Presidential Museum, explore the Frederik Meijer Gardens & Sculpture Park, and enjoy the city’s craft beer scene.

If you’re into museums, Grand Rapids is for you. Explore the Gerald R. Ford Presidential Museum, the Grand Rapids Public Museum, and the Grand Rapids Art Museum. After touring the museums, check out the Frederik Meijer Gardens & Sculpture Park, with indoor and outdoor gardens and galleries.

It’s very easy to spend all day there, so decide which highlights you want to see before visiting to maximize your time. Grand Rapids is also known for its burgeoning beer scene, so top off the day by grabbing a drink at one of its many craft breweries.

Things to Consider

Chicago isn’t just a city; it’s a launchpad for incredible weekend adventures. Whether you’re craving the scenic beauty of nature, the charm of small-town life, or the excitement of a vibrant city, the Midwest has it all.

Additionally, if you’re in the market for a new apartment, Draper and Kramer offer an extensive portfolio of luxury rental properties in Chicago and various other cities.

The following Chicago-based Draper and Kramer buildings offer proximity to the weekend getaways mentioned in this article:

Aerial view of the Chicago skyline with skyscrapers, highlighting the city's architectural landscape.

Gateway to Adventure: Explore the vibrant pulse of Chicago against the iconic backdrop of its skyline, setting the stage for unforgettable weekend getaways nearby.

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