Travel & Living

Keep Midwest Princess Summer Going With All The Region's Best Hidden Gems

From Michigan's best small towns to Minnesota's forested beaches, see all the best the Midwest has to offer for your late summer getaway.

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Chappell Roan during her Midwest Princess tour on June 1, 2024. Photo via Instagram/@chappellroan

While the coastal regions of the United States have their own unique attractions that warrant a visit, if you're in need of a late summer mini-vacation, there's no better area to visit than the Midwest. Whether you're looking to stay in a charming upscale bed and breakfast in a small town or set on embracing your adventurous spirit with all of the outdoor activities the natural regions of the Midwest have to offer, you're sure to enjoy the final days of summer in peace. 

No matter if a visit to the Midwest means a trip back to your home territory, or if this vacation presents new opportunities, a perfectly planned getaway means escaping the crowds that flock to the beach towns of California and the tourists and townies alike that reside in New England's most popular summer spots.  While the region has been full of pride for years, the emergence of self-proclaimed Midwest Princess herself, Chappell Roan, as this season's biggest superstar has people embracing everything the area has to offer. 

Looking to bring out your inner Midwest princess? Join L'OFFICIEL as we break down all of the hidden gems to visit within the region, including the best small towns, beaches, national parks, and more. 

Beaches, Landmarks, and Natural Wonders

Apostle Islands, Wisconsin

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midwest travel guide : where to travel in the midwest : best beaches wisconsin
Apostle Islands lakeshore, Wisconsin. Getty Images.

If you're looking to maximize your outdoor time this season, opt for a visit to the Apostle Islands in Wisconsin. These stunning natural rock formations prove perfect for snapping photos, and also serve as an engaging location for all the activities you're seeking. From a day out on the lake kayaking to low-key hikes along the coastline, there's plenty to see and do in the natural splendor of the region. For those unfamiliar with the area, be advised that the Apostle Islands are quite a distance from Wisconsin's major cities, to be sure to plan accordingly if you're making a day trip of the destination, or opt to stay local at one of the many AirBnbs available nearby. 

Lake Itasca, Minnesota

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Lake Itasca, Minnesota. Getty Images.

Locals and tourists alike favor Lake Itasca as a leading Minnesota summer travel destination. With cold, refreshing crystal clear waters and sprawling sandy beaches, there's no time like late summer to visit one of Minnesota's most beloved lakes. Whether you opt to enjoy the lakefront itself or the miles of trails perfect for leisurely walks and bike rides, there's no shortage of outdoor fun to be had. 

Pictured Rocks, Michigan

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Pictured Rocks, Michigan. Getty Images.

Among Michigan's most famous natural landmarks, the Pictured Rocks, nestled in a cove on the Upper Peninsula, are one of the state's most unique natural sites. From miles-long trails amid picturesque birch trees to lookout points where viewers can spot the remnants of the many shipwrecks that reside in Lake Superior, the Pictured Rocks National Park is a must-visit landmark for nature-lovers and certified cosmopolitan girls in need of a break from the city alike.

While the famous Pictured Rocks themselves are no doubt the main attraction, the area also boasts gorgeous waterfalls, cozy inland lakes, and serene beaches.

Small Towns and Cities To Visit

Suttons Bay, Michigan

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Sleeping Bear Dunes near Suttons Bay, Michigan. Photo via Instagram/@brady_mcdonough

While Traverse City is no doubt the most popular tourist destination in northern Michigan, beat the summer crowds with a stay in Suttons Bay instead. With a charming downtown area, a serene beachfront, and plenty of cozy cafés and restaurants to visit, Suttons Bay serves as the perfect home base for all of your adventures in the area. Restaurants like Martha's Leelanau Table, Streetside Grille, and the 45th Parallel Cafe are all iconic culinary spots within the town, but be sure to venture into Traverse City for other equally as thrilling spots. 

As a prime agricultural location, northern Michigan is home to plenty of sprawling orchards, hop vineyards, and fields, making for some of the best breweries and local wineries in the Midwest. Whether you're in the mood for a refreshing beer, a flight of premium hard apple ciders, or a wine tasting, you're sure to find countless incredible options. 

During the day, be sure to check out the many beaches that Lake Michigan has to offer. For some of the best hikes in the area, take a day trip to the Empire Bluffs or Pyramid Point, where you'll find fun, yet challenging hikes with stunning views throughout your journey. 

Whether you opt to stay at a local bed and breakfast or rent a house through services like Vrbo or Airbnb, the charming natural landscapes are sure to reel you in summer after summer. 

Madison, Wisconsin

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midwest travel guide : where to visit in the midwest during summer : where to go in wisconsin summer
Capitol building and lakefront view in Madison, Wisconsin. Getty Images.

Madison, the capital city of Wisconsin, makes for a pleasant visit any time of year, but it's especially stunning in the summer. As an added bonus, Madison tends to be less busy in the summer, as many of the university students will have flocked home for the off-season. With greenery lining the charming streets and a sparkling lake to either side of the city, the landscape is second to none. 

Whether you opt to spend an afternoon kayaking on the lake or strolling the streets perusing record stores, boutiques, and local coffee shops, Madison has something for each and every visitor to enjoy. 

Every Saturday, the square next to the capitol building hosts a massive farmer's market with loads of fresh fruit, delicious produce, and plenty of beloved baked goods to try out. Whether you're in the mood to sample some of the region's finest artisanal snacks or are simply on the hunt for your morning caffeine fix, you'll delight in the hustle and bustle of the weekly event.  

Chicago, Illinois

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midwest travel guide : where to go in chicago during summer : best things to do in chicago
Chicago Riverwalk; Lincoln Park flower garden in Chicago. Getty Images.

From the Chicago Riverwalk to the famous Millenium Park to the ultra-chic neighborhood of Lincoln Park, the biggest city in the Midwest is a classic summer travel destination for good reason. With tons of restaurants to choose from, a selection of some of the world's leading museums, and stunning, clean public beaches to visit, it's no secret why visitors flock to the city during the sweltering summer season. 

Whether you're looking for a quick bite to eat or a full-fledged hours-long meal, the many neighborhoods of Chicago have plenty of options. For those on the hunt for a classic Chicago deep-dish pizza, head to Pequod's Pizza right outside of Lincoln Park. Italian restaurants are far from few in the city, so chances are, wherever you end up, you'll enjoy delicious pasta, fresh salads, and traditional dishes, but among the most revered spots are Monteverde and Osteria Langhe. For brunch, check out Lula Cafe in Logan Square, where you'll find classic breakfast dishes and lunch specials done right at one of the longest-standing brunch spots in town. While New York City's Chinatown neighborhood may be famous in its own right, Chicago's Chinatown is a close rival, if not an equal, in terms of unparalleled food and drink offerings, so if you're on the hunt for a satisfying, culinarily enthralling meal, be sure to check it out. For avid fans of Chicago-based hit TV show The Bear, be sure to sample one of the city's most iconic food feats—Italian beef—at renowned spots like Johnnie's Beef. 

The Art Institute, Shedd Aquarium, and The Bean—officially known as Cloudgate—are just a few iconic Chicago landmarks, but if you're looking to broaden your horizons on your next trip to the city, opt to explore the botanical gardens in Lincoln Park, the many vintage shops in Logan Square and Wicker Park, or take a drive to the North Shore and visit some of the best beaches in the area in towns like Glencoe, Wilmette, and Winnetka. Looking to catch a Chicago baseball game this summer? Embrace the local spirit and check out a Chicago Cubs game at Wrigley Field or a White Sox game south of Chinatown. While either option is equally enticing, for those in search of a longer stint out, head to a Cubs game in Wrigleyville and stick around afterward at one of the many bars in the area, which is sure to be a good time whether the team wins or loses. 

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