From the Magnificent Mile to Navy Pier and beyond, there’s a great deal to keep Chicago residents busy during their leisure time. But sometimes it’s nice to get out of the big city, especially during hot summer days. Fortunately, there are countless beautiful Midwest vacation destinations located just a few hours from Chicago.

Here are five ideas for your next weekend getaway from Chicago. All are fewer than 150 miles from downtown Chicago.

Getting There

We recently discussed how the pandemic caused more Chicago renters to think about buying a vehicle. However, if you are a city dweller without a car, a weekend rental is always an option. Rental agencies catering to weekday business travelers may offer weekend discountsAmtrak will whisk you to many of these worthy destinations as well.

1. Saugatuck, MI – 142 miles

Saugatuck has ranked among the best lake towns in America. The community delivers ample doses of relaxation via pristine beaches, cozy inns, and art galleries. Interstate highways I-94 and I-196 make it simple to travel by car, but you can even get there by train. Head to Chicago’s Union Station and board Amtrak’s Pierre Marquette train. It will take you to Holland, where you can take a taxi the final 12 miles to Saugatuck.

Hike the dunes at Saugatuck Dunes State Park and fly a kite along the beach. Or, rent a boat and explore the lake. Cycling enthusiasts can take off down one of the scenic bike trails. If you drive, consider a stop at Indiana Dunes National Park on the way there or back. The park encompasses an impressive 15 miles of Lake Michigan shoreline.

2. Lake Geneva, WI – 83 miles

It is hard to believe a community of 8,000 offers so many opportunities for fun and relaxation. Although browsing the downtown shops is great fun, it can get a little busy on summer weekends. Fortunately, there’s much more to do around the lake and beyond. Lake Geneva’s maximum 144-foot depth helps keep its waters cool and clear. Consider a sunset cruise or stroll any part of the 26-mile Lake Shore Path as it winds its way along the lake and through the woods. Board a hot air balloon for an unforgettable evening flight.

Or, explore the smaller lake communities like Williams Bay, Lake Delavan, and Fontana. The rec department in Williams Day offers kayak and paddleboard rentals at modest nonresident rates. The historic Yerkes Observatory, which is located in William Bay, was been operated by the University of Chicago between 1897-2020. It will re-open in 2021 following restoration by the Yerkes Future Foundation.

Pamper yourself at the Grand Geneva Resort & Spa, a AAA Four Diamond resort. Grand Geneva offers golfers 36-holes of championship golf. For a classic Wisconsin supper club experience, dine at the century-old Mars Resort. It is on Lake Como, just four miles from downtown Lake Geneva.A boat tours boat flying several American flags with fall trees in the background.

#3 Milwaukee Lakefront – 93 miles

You’ll find both the Milwaukee Art Museum (MAM) and Discovery World Science and Technology Museum on Milwaukee’s lakefront. The art museum dates to 1888, while Santiago Calatrava’s famous contribution is just 20 years old. The art museum addition, often referred to as “The Calatrava,” boasts a brise soleil with a maximum wingspan of 217 feet. Just to the south are the Summerfest grounds. For 2021, the world-famous music festival is scheduled for the first three weekends in September.

As you exit the art museum, consider a stroll north along the lake. Rent a specialty bike for four or hop aboard a Segway to explore the lakefront. Or, you can rent a paddleboat and explore the 14-acre Juneau Park Lagoon, teeming with wildlife.

Dine right along the lake at The Harbor House (550 N. Harbor Drive). Or, select from top-rated downtown restaurants. Examples include Bacchus (925 E. Wells), Sanford (1547 N.Jackson), and Ward’s House of Prime (540 E. Mason). Less than a half-mile from the art museum, savor great views and drinks at Blu. It is a bar on the 23rd floor of the luxurious Pfister Hotel. To get to Milwaukee, take the train to Milwaukee or head north on I-90/94 or U.S. 41.

4. Starved Rock State Park – 94 miles

Starved Rock State Park is often rated as one of the state’s foremost natural attractions. It is a wondrous place replete with soaring bluffs and 18 canyon waterfalls. The park offers 13 miles of hiking trails. Enjoy a picnic while savoring the views or go fishing or boating on the Illinois River.

Register for a free guided tour available from June to November. Take a wildflower walk in the spring or a fall colors hike in October. Set out on a river cruise, or sign up for one of the waterfall and canyon trolley tours.

Ottawa is a historic community at the confluence of the Fox and Illinois Rivers. It is a gateway to the park. Consider a stay at the century-old Starved Rock Lodge. The facility offers both rustic lodging and charming cabins. The area also offers a selection of quaint inns and comfortable bed-and-breakfasts.

5. Kohler, WI – 145 miles

Kohler’s American Club is a five-star resort in a serene setting. It offers luxury accommodations, spa services, and world-class golf. The hotel is in a Tudor-style structure dating to 1918. Kohler plumbing products grace the rooms. Tour the futuristic lighting, bathroom, and kitchen displays at the Kohler Design Center or visit the Kohler Waters Spa, which is the only Forbes five-star rated spa in the state.

Kohler is also home to world-class golf. Both Blackwolf Run and Whistling Straits have hosted major golf championships. The 2012 U.S. Women’s Open and the 2015 PGA Championship are two examples. From September 24-26, 2021, Whistling Straits will host the Ryder Cup. This is a premier golf event pitting U.S. golfers against their European counterparts.

Kohler-Andrae State Park is just eight miles away. Explore the Lake Michigan shoreline or set out on the boardwalk that traverses the dunes.

About Draper and Kramer

Draper and Kramer is a family-operated real estate firm serving Chicago since 1893. Visit our website to browse our luxury apartment properties in Chicago or schedule an apartment tour today.

The Milwaukee lakefront looking from across the harbor.

Sometimes it’s nice to get out of the big city, especially during hot summer days. Fortunately, there are countless beautiful Midwest vacation destinations located just a few hours from Chicago, like the Milwaukee lakefront seen here.

Keep Tabs on Us

Industry updates, insights, and Draper and Kramer news—all delivered straight to your inbox.