7 Best Weekend Getaways from Chicago

Chicago is the third-largest city in the United States after New York and Los Angeles. This huge metropolis is a vibrant and exciting place to live or visit, and there is plenty to do within the city limits. However, Chicago is also extremely well-connected and conveniently located as a kick-off point for fun-packed weekend trips to other parts of the Midwest.

If you want to escape the hustle and bustle for a day or two, several fantastic towns and cities are within easy driving distance. From a vacation home stay atop a private dune in Miller Beach to a culture-filled weekend in Milwaukee, these are the seven best weekend getaways from Chicago.

1. Miller Beach, Indiana

Photo Credit: Steve Johnson via Flickr CC2.0

Miller Beach is a charming neighborhood just 40 minutes from Chicago, making it one of the most convenient road trips from the Windy City. Located on the southernmost point of Lake Michigan, this beautiful small town is the perfect big city antidote with its lush natural landscape, great food and drink, and endless opportunities for relaxation.

Fans of the great outdoors will appreciate that there are over 20 miles of biking and hiking trails to explore. These well-maintained pathways stretch from the Miller South Shore train station to Indiana Dunes National Park, the Marquette Greenway, and beyond. If you prefer to kick back and relax, Lake Street Beach is an idyllic lakefront spot for that.

Visitors who want to get out on the water will appreciate the lake’s naturally-occurring sand bars that protect the shore and allow for safe swimming, boating, and kayaking.

There are plenty of excellent dining options in Miller Beach, including Flamingo Pizza, Vibrations Juice Bar, and Tequila and Tacos. Beer fans should add a trip to 18th Street Brewery to the weekend’s itinerary to try one or two of their signature brews.

2. Milwaukee, Wisconsin

Photo Credit: Paulo Nabas

Milwaukee is the home of beer, cheese, and great museums, making it a fantastic option for a food and culture-packed weekend getaway.

You could easily fill a day enjoying the city’s many museums. The Milwaukee Art Museum is an architectural wonder that houses nearly 25,000 pieces of world-class art. It’s worth a visit, even if it’s only to take in the magnificent building itself. The Milwaukee Public Museum is another fascinating way to spend a morning discovering everything from a full-size recreation of the streets of Milwaukee in the late 19th century and early 20th century to a butterfly garden and extensive fossil collection. Petrolheads shouldn’t miss the Harley-Davidson Museum.

Reward yourself after a day of museum hopping with a trip to one of the city’s many pubs and breweries to sample an authentic Milwaukee brew. Choose between local small-batch craft beers and a pint of Miller in the famous brew’s home city.

The drive time is one and a half hours, or you can hop on the Amtrak, so Milwaukee could also be done as a day trip if you’re short on time.

3. Lake Geneva, Wisconsin

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Lake Geneva is a top pick for a rejuvenating weekend getaway in Wisconsin. Just 90 minutes from Chicago, this easily accessible year-round destination has plenty to do, whether sunny or snowing.

In the summer months, visitors can take advantage of kayaks, wave runners, and power boat rentals to explore the lake’s calm waters. Or, if you want to relax, a picnic on one of the beautiful beaches is hard to beat. If you visit in winter, don’t miss the Ice Castles, where you can see mind-blowing icicle displays. Other outdoor activities include adrenaline-fueled zip-lining, rugged state parks, and an exhilarating hike along the 21 miles of trails around the lake.

There’s plenty to see and do in Downtown Lake Geneva. Fans of retail therapy will appreciate the range of boutique stores and dozens of restaurants, cafes, and bars to explore. One of the area’s most-loved attractions is the Lake Geneva Magic Show Theater, where you can experience must-see magic and illusion shows. 

4. Saugatuck, Michigan

Photo Credit: Philip Mowbray

If you’ve got a summer weekend to spare, consider driving the 2.5 hours to the lakeside town of Saugatuck, Michigan. Visitors from throughout the Midwest flock here when the weather is good to enjoy the laid-back vibe and outdoor activities.

Oval Beach is known as the best beach in Michigan and is a favorite spot for locals and visitors to soak up the sun on the shores of Lake Michigan. Stroll along the picturesque boardwalk or hire a paddle board or kayak for an on-the-water adventure. There are also regular sunset sailboat cruises which make for a wonderfully romantic end to the day.

Saugatuck is known as the ‘art coast of the Midwest,’ no trip is complete without a visit to one of the city’s art galleries. Watch for art classes and fairs during your trip, because arty events are a big part of Saugatuck life and can be a fun way to pass an afternoon.

There are plenty of charming bed and breakfasts in Saugatuck, so it’s worth spending a night or two to soak up the atmosphere and enjoy some serious R&R.

5. Indianapolis, Indiana

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Indianapolis, which is known by locals as ‘Indy,’ is a three-hour drive from Chicago and is a great destination for families looking to escape the city for the weekend.

The Children’s Museum of Indianapolis is a fun-packed place with interactive exhibitions that kids will love, and the Indianapolis Zoo gives the entire family an opportunity to meet their favorite wild creatures. If there’s a sports fan in your group, you shouldn’t miss the Indianapolis Motor Speedway, where you can watch the best racers in the business zip around the track at hair-raising speeds.

If you’re looking for an adult-friendly getaway, check out the Broad Ripple neighborhood and its superb nightlife, shopping, and dining. For culture vultures, the Massachusetts Avenue Arts District has the highest concentration of theaters and galleries than anywhere else in the city.

6. Wisconsin Dells, Wisconsin

Photo Credit: Aaron of L.A. Photography

Wisconsin Dells is another family-friendly destination situated three hours from Chicago. It’s known as ‘the waterpark capital of the world,’ so it’s a must-visit if that’s your thing. Noah’s Ark Water Park, the largest waterpark in the US, is located here and has more than 20 wet and wild attractions with varying intensity levels and age limits. There are rides for everyone here, and with several dining options available, you can really make a day of it.

If waterparks aren’t your thing, there are many other activities to enjoy. These include visiting local wineries and breweries or taking a scenic boat ride through the Dells. Wisconsin Dells is also home to several world-class golf courses, making it a top weekend destination for anyone looking to hit the links.

7. Galena, Illinois

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If you’re looking for a charming town known for its rich history and 19th-century architecture, Galena is a superb option. Illinois’ best ski mountain is located here, making it a mecca for winter spots, but there’s plenty to do at any time of the year.

Galena sits alongside the Mississippi River and is three hours from Chicago by car, meaning it is conveniently located for an overnight stay or a weekend escape. The historic downtown area is home to over 100 stores and boutiques, and the centuries-old buildings create a relaxed, old-world feel.

For an ultra-relaxing getaway, head to Eagle Ridge Resort & Spa. This 6,800-acre property has a luxurious spa offering an extensive menu of treatments and experiences and a large swimming pool. Golf fans will appreciate the four golf courses, and 22 miles of biking and hiking trails provide plenty of outdoor adventures to keep nature fans occupied.

Other Chicago Weekend Getaways

This list wouldn’t be complete without honorable mentions for the following spots within driving distance of Chicago:

  • Starved Rock State Park, Illinois — in just two hours, you can be in this hiker’s paradise with its dramatic cliffs and spectacular waterfalls.
  • Holland, Michigan — this city’s Dutch heritage makes a unique weekend getaway, and it’s only a 2.5-hour drive away.
  • Madison, Wisconsin — also 2.5 hours away is this charming city that foodies and families will love.
  • Door County, Wisconsin — 4.5 hours from Chicago-you’ll find a historic and adventure-filled getaway in Door County’s natural setting. 

7 Weekend Getaways That You’ll Never Forget

A weekend break from Chicago couldn’t be easier, thanks to the many fun-packed options just a short distance away. From a stay at a relaxing Miller Beach vacation home to Wisconsin Dells waterpark adventure in as little as 40 minutes, you can experience the best of US culture, history, and nature. So what are you waiting for? Pack up the car or hop on a train and get ready for a weekend getaway to remember!

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