Things To Do Near Chicago This Weekend

Chicago is the largest city in the Midwest and a major center of culture, business, and architecture. As the third largest city in the United States, Chicago is a bustling metropolis full of energy and excitement. With its iconic skyline, world-class museums, and stunning lakefront trails, it is no wonder that Chicago draws millions of visitors each year. From outdoor adventures and live music to world-class restaurants and cultural attractions, there is something for everyone to enjoy in this vibrant city. Whether you are visiting for the weekend or planning a longer stay, here are some of the best things to do near Chicago this weekend.

Explore the Magnificent Mile

The Magnificent Mile is one of the most famous streets in Chicago, running along North Michigan Avenue from the Chicago River to Oak Street. Here you can find some of the city’s most iconic attractions, including the historic Tribune Tower and Tribune Company Building. It’s also home to some of the best shopping, dining, and entertainment in the city. Explore its many stores, restaurants, and galleries, or take a stroll along the scenic waterfront.

Dine at a Local Restaurant

Chicago is known for its diverse food scene, offering something to suit every taste. From classic deep-dish pizza to fine-dining restaurants, there are plenty of delicious options to choose from. Visit local eateries like Smoque BBQ, Alinea, or Girl & The Goat for an unforgettable dining experience. For a more casual setting, try one of Chicago’s many street food vendors or visit one of the city’s popular food halls.

Take in a Show at The Theater District

The Theater District is one of the most popular destinations in Chicago. Located in the heart of downtown, it is home to some of the city’s most prestigious theaters and performance venues. Catch a show at one of these iconic theaters and experience the best of Chicago’s performing arts scene. From comedy clubs to Broadway musicals, there is something for everyone at The Theater District.

Visit Lincoln Park Zoo

Lincoln Park Zoo is one of the oldest zoos in the United States and home to over 1,200 animals. Explore its many exhibits and discover a variety of species from around the world. The zoo also offers educational programming and plenty of activities for kids. From camel rides to birdwatching, there is something for everyone at Lincoln Park Zoo.

Take a Tour of the Windy City

Experience all that Chicago has to offer with a guided tour. You can explore the city’s iconic landmarks and neighborhoods on foot or by boat. Take an architectural boat tour on the Chicago River or hop on a bus tour to get a comprehensive overview of the city’s history and culture. You can also take a walking tour of downtown or explore iconic neighborhoods like Wicker Park and Lincoln Park.

Enjoy Lake Michigan

Lake Michigan offers endless opportunities for outdoor fun and exploration. Take a leisurely stroll along its miles of sandy beaches or rent a kayak or paddleboard to explore its vast waters. Visit Navy Pier for spectacular views of the city skyline or take a harbor cruise for a different perspective. For an adrenaline rush, try parasailing or jet skiing on Lake Michigan.

Shop at The Magnificent Mile

The Magnificent Mile is home to some of the best shopping in Chicago. From designer labels and luxury boutiques to discount stores and trendy shops, you’ll find it all here. Shop for designer clothing and accessories at stores like Neiman Marcus and Bloomingdale’s, or check out one of the many discount outlets along the mile. You can also find unique souvenirs from local artisans at The Magnificent Mile’s many specialty stores.

Explore Millennium Park

Millennium Park is an iconic destination in downtown Chicago. Visit this 25-acre public park to enjoy its many attractions, including an interactive fountain, reflecting pool, and massive outdoor ice rink in wintertime. You can also explore its lush gardens, public art installations, and outdoor music venues. On weekends, there are often free concerts and performances taking place in Millennium Park.

Sample Famous Craft Beer

Chicago is known for its craft beer scene, with over 100 breweries located throughout the city. Sample some of its local brews at popular breweries like Revolution Brewing or Goose Island Brewery. You can also find beer tastings at many local pubs and restaurants or sign up for a craft beer tour to explore multiple breweries in one day.

Take a Food Tour

Sample some of Chicago’s best cuisine on an immersive food tour. From deep-dish pizza to hot dogs and Italian beef sandwiches, you can taste it all on a guided tour around the city’s most popular eateries. Try global flavors from Chinatown or explore unique flavors from Little Italy. Tours often include stops at local markets and food stands too, giving you an authentic insight into Chicago’s culinary culture.

Book an Architecture Boat Tour

Explore Chicago’s iconic architecture from a unique perspective with an architecture boat tour on the Chicago River. Enjoy stunning views of downtown as your guide explains the history behind some of the city’s most famous buildings. See how skyscrapers were constructed over time or learn about architectural styles like Beaux-Arts and Art Deco. This is one of the best ways to appreciate Chicago’s stunning skyline from a different angle.
Book an Architecture Boat Tour through Viator here.

Book a Segway Tour

Explore Chicago’s vibrant neighborhoods on a Segway tour. Glide through downtown while your guide points out famous landmarks like The Bean and Millennium Park. Or take a more leisurely ride through neighborhoods like Wicker Park or Lincoln Park and learn about their unique history and culture as you go. This is one of the most convenient ways to cover large distances while still enjoying an up-close look at some of Chicago’s most iconic sites.
Book a Segway Tour through GetYourGuide here.

Book a Tasting Tour

Sample some of Chicago’s best drinks on a tasting tour around town. Visit local breweries to sample craft beer or explore some of the city’s popular distilleries for craft cocktails and spirits. You can also visit wineries near the city for wine tastings or explore trendy neighborhoods like Wicker Park for artfully crafted cocktails at speakeasies and lounges.
Book a Tasting Tour through GetYourGuide here.