Milwaukee, Wisconsin - Weekend Getaway in and around Chicago

7 Top-Rated Midwest Weekend Getaway In and Around Chicago (2024)

Chicago, no doubt, is a beautiful city. However, once in a while, everyone needs a break from the usual, and it is when you can plan a weekend getaway from Chicago. Every Chicagoan who wants to rejuvenate should not hesitate to explore the nearby places. While the weather is pleasant, never underestimate the power of a great road trip and a leisurely weekend. It can be within the State of Illinois or the other American states surrounding Lake Michigan; options will never fall short. From Geneva to Wisconsin and Missouri, options for a Midwest weekend getaway are in abundance.

Midwest experiences four different seasons; thus, every time you visit a new place, you’ll experience diverse seasons. While winters are all about festivity and snowfall, springtime speaks of flowers and fragrances. And when it is summers, beaches, and Midwest’s very own jewel Lake Michigan awaits you.

7 Top-Rated Midwest Weekend Getaway In and Around Chicago

Thus, some of the popular and unmissable weekend getaways in and around Chicago with all this in mind.

1. Milwaukee, Wisconsin

(92.1 miles or 1 hr and 28 minutes from Chicago)

Milwaukee is a beautiful city located on the western shore of Lake Michigan. Wisconsin’s largest city, Milwaukee, is ideal for solo, couple, or family weekend trips in Midwest. It teams with two things that westerns love the most, Beer and Museums. As the city has played a major role in U.S. beer production, you can raise a toast and celebrate its heritage. Also, your Saturday evening is sorted for a slow and pleasing walk because it is a riverside city. For tasting some great locals flavors, you can hop on the Milwaukee Food and City Tour. Along with that, there are plenty of attractions, including parks, historical landmarks, a Planetarium, and more.

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2. Starved Rock State Park

(93.3 miles and 1 hr and 31 minutes from Chicago)

If Illinois has your limits, then the Starved Rock State Park can prove the best Midwest weekend getaway for you. Located in LaSalle County, the State Park is a world apart from anything else and Illinois’s most priced possession. It is known for its fascinating rock formations, canyon waterfalls, and finest camping and hiking opportunities. You can book your weekend stay right inside the Park at the Starved rock lodge. The best time to be here is either spring or late after the monsoon. It is when the waterfalls are at their highest lush, whereas trees are painted into beautiful shades of red. While planning, make sure you carry along with ample mosquito and insect sprays and good hiking shoes.

Starved Rock State Park - Weekend Getaway in and around Chicago

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3. Rockford, Illinois

(88.8 miles or 1 hr and 28 minutes from Chicago)

Also known as the Forest city of Illinois, Rockford is one of the biggest cities in the State, though it has a small-town vibe. The city is known for its historical, cultural, and natural attractions. On a Midwest weekend getaway, you can begin with the Anderson Japanese Gardens and observe the most tranquil surroundings. Further on your itinerary, add Rockford Museums like Midway Village Museum and Burpee Museum of Natural History. When in Rockford, you cannot miss visiting the Rock Cut State Park, the city’s natural playground. For a relaxed stay, either choose from B&Bs or go for resort camping.

Anderson Japanese Gardens - Weekend Getaway in and around Chicago

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4. Indianapolis, Indiana

(183.2 miles or 2 hr and 56 minutes from Chicago)

Affectionately known as Indy, Indianapolis is a typical Midwestern city. It sits on the White River, the Southeast of Lake Michigan, and has several unique things. One of the biggest draws here is the Indianapolis Motor Speedway, where you can become a spectator and enjoy your time. Or, while the weather turns favorable, walk through the three-mile Canal Walk and admire the city like locals. A great escape from the city’s hustle and bustle calls you at the White River State Park, the downtown itself. The Park alone boasts several top-rated tourist attractions of Indianapolis. The city also boasts a number of great museums along with the visit-worthy Zoo and Natural preserve. For your stay, choose a hotel near Monument Circle and make navigation easier.

Indianapolis Motor Speedway - Weekend Getaway in and around Chicago

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5. SevenOaks, Geneva

(84.9 miles or 1 hr and 30 minutes from Chicago)

SevenOaks isn’t a tourist attraction or city but a pleasing hotel in Geneva, Wisconsin. It is situated 2 miles from Big Foot Beach State Park and a 10 minutes’ walk away from the city’s downtown. The beautiful hotel property is set amidst trees that infuse a relaxing vibe. This adult-only hotel is ideal for a weekend getaway from Chicago. Or, if you want to spend some quality time with your partner, SevenOaks will make a wonderful place. While the cottages are warm and inviting, owners will attend and serve you with personalized attention. They serve you complimentary breakfast, complimentary wine and cheese, and up-class hospitality. Though the hotel is enough on its own, you can explore the downtown area for some added fun.

SevenOaks, Geneva - Weekend Getaway in and around Chicago

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6. Grand Geneva Resort & Spa

(82.8 miles or 1 hr and 27 minutes from Chicago)

The Grand Geneva Resort & Spa is an astounding property and a beauty that you will never forget. The resort is located between Milwaukee and Chicago and 3 miles from downtown Lake Geneva. The highlight here is two championship courses set around a small lake/ pound which indeed looks natural. There’s something or the other to do all year round at Grand Geneva, be it snowboarding, skiing, golfing, cycling, or horse-riding. You can come here for your honeymoon trip, a leisurely family weekend, or an adventures getaway. Along with beauty and fun, the resort is filled with countless amenities and services, every point appreciable. For some added fun, visit the nearby Moose Mountain Falls Waterpark or the downtown region.

Grand Geneva Resort & Spa - Weekend Getaway in and around Chicago

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7. Indiana Dunes National Park

(44.6 miles or nearly an hour from Chicago)

Indiana Dunes National Park makes the perfect Midwest weekend getaway from Chicago. It is located on the southern shore of Lake Michigan and is one of the Newest National parks of the United States. The Park is covering 15,349 acres that offers access to the beautiful Lake Michigan. It is home to three dunes, including 176 ft Mount Jackson, 184 ft Mount Holden and 192 ft Mount Tom. You can access walking and biking trails or hike along the dunes. Or go for beach kite flying, fishing, swimming, or cross-country skiing. The National Park also provides several opportunities to explore historic homes, including Swedish Farmsteads Historic District, Lustron Homes, and Bailly Homestead. For a comforting weekend stay, there are a lot of hotels, Inns, and B&BS available around.