22+ Best Things to Do in Chicago This Weekend

Everyone is well-aware that Chicago is known as the Windy City, but there’s more to this breezy town than meets the eye with a plethora of things to do and places to go this weekend. Be sure to check out this guide to our favorite 22 things to do this weekend in Chicago.

#1: Laugh at The Second City Comedy Club

The state of Illinois has given birth to plenty of legendary comedians over the years, including SNL (Saturday Night Live) alumni John Belushi, who was born right here in Chicago. The Animal House star performed at The Second City on Wells Street in the distant past along with appearances by Dan Aykroyd, Tina Fey, and Amy Poehler – just to name a few. 

With this kind of laughing track record, chances are you’re likely to see a performer honing their comedic skills there before appearing on-screen in the future. Tickle your funny bone at this popular comedy club this weekend with unique improv performances, hilarious sketches, special guest appearances, and more.

#2: Feast on Chicago’s Best Food Tours

Chicago deep dish pizza

Source: Flickr

Chicago is world-famous for its namesake deep-dish pizza not to mention (but we will) enormous hot dogs buried under a mountain of toppings, Italian beef sandwiches, cold and crisp craft beers and so much more. To discover these big portions and bold flavors the best way to uncover these tasty sensations is by booking a food tour in Chicago. These pre-planned journeys deliver more than a few destinations or a single type of food when you consider:

If any or all of these events have your taste buds tantalized, be sure to reserve a spot in advance to guarantee your slot. Get in touch with friends and family beforehand and make these outings a memorable part of your relationship. They also make a great gift or way to commemorate a special occasion like an anniversary, graduation or just an excellent getaway in Chicago on the weekends.

#3: Explore the West Loop

What this neighborhood lacks in retail shops, it makes up for in swanky corporate headquarters (McDonald’s and Google, we’re looking at you) and it offers dining options in spades! We’re incredibly lucky to have some of the greatest restaurants this city has to offer all in one easily walkable area. 

Hunger in the West Loop is… not a thing.

Randolph Street, aka Chicago’s Restaurant Row, is home to multiple star-rated Michelin restaurants, Blackbird and The Loyalist, alongside more attainable fair (but packed with just as much yum as far as we’re concerned). For example, Au Cheval won best burger in the country a few years back. Hot tip — visit this spot at off-peak hours to avoid a 2-hour wait (although it is worth the wait).

But you don’t have to explore the wonders of this neighborhood on your own!

On the #1 TripAdvisor Rated Gateway To The West Loop Food Tour, you’ll experience an impressive introduction and subsequent deep dive into the West Loop’s renowned and extensive food and restaurant scene. 

You’ll enjoy a leisurely stroll down Randolph Street, often referred to as “Chicago’s Best Foodie Street,” and learn why this distinction comes as no surprise to locals living in the area as its home to a unique mixture of James Beard Award-winning chefs, old school diners, Chicago-based breweries and eclectic dive bars. The diversity of this culinary hub allows us to feature master chefs ranging from the founder of a burger bar that’s rated by the Food Network as one of the best hamburgers in the country, to an award-winning restaurant that has created over 1,500 different pizza recipes.

#4: Take a Selfie at The Bean

Chicago Cloudgate Bean

Source: Pexels

There are so many unforgettable sites to see in Chicago it’s hard to single one out but there’s one at the AT&T Plaza Millennium Park that’s definitely worth a visit. The anchor piece of this stunning park is the Cloud Gate public sculpture erected in 2006 by renowned artist Anish Kapoor.

Also known as The Bean, this enormous rounded arch is decorated with 168 highly reflective seamlessly joined stainless steel plates measures 33-feet high, 42-feet wide, 66-feet long and weighs around 110 tons. It’s become an emblem as a part of the 21st century Chicago landscape and a popular backdrop for selfies.

#5: Visit the Chicago Picasso 

Yet another opportunity for a spectacular snapshot is located in the Daley Plaza where the Chicago Picasso piece was unveiled on August 15, 1967. It was commissioned by architect Richard J. Daley who designed his namesake center in the early sixties.

Although the piece was untitled upon creation and presentation, the sculpture was rumored to represent the French model Lydia Corbett who sat for a series of drawings done by Picasso in the fifties. The sculpture was considered controversial at the time but has become a landmark for the city.

#6: Capture the Magic at Buckingham Fountain

For more magical moments to capture on smartphones head over to the Buckingham Fountain in the famed Chicago Loop at the center of Grant Park. Constructed in 1927 from Georgian pink marble, it’s one of the largest fountains in the world with 200 jets shooting streams over statues more than 25-feet tall across a pool nearly 300-feet in diameter. After the sun sets, lights reflect upon, all around and throughout the water making this the perfect setting for some picturesque photo ops. 

Source: Pexels

#7: Stroll Along the Chicago Riverwalk

Chicago pedway system

Source: Pexels

The City of Chicago continues to expand on its phenomenal feat of urban planning when constructing The Riverwalk along this namesake waterway running through the downtown district. While traversing this trail, visitors are treating to stunning artwork like a number of smaller colorful graffiti panels or the large-scale installation of Ellen Lanyon’s Gateway presentation showcasing the story of Chicago on 28 ceramic tile murals.

Options to travel on the river itself include water taxis, taking a boat tour, tackling a journey in DIY mode on an urban kayak or cycle boat. Many riders take Chicago’s floating taxis to travel from one waterfront tourist location to another.

#8: Trek the Lakefront Trail

Chicago lakefront trail

Source: Choose Chicago

All four of Chicago’s lakeside City Parks are accessible on 18 miles of a paved pathway shared by walkers, joggers, and cyclists on the Lakefront Trail. Some local residents use the trail to get to work while others on the weekends will soak in the Chicago skyline or stroll along the shoreline.

You can also use the path to reach the South Shore Cultural Center, the Shedd Aquarium or the Navy Pier. To get around faster, there are bike rental stations along the way with some offering day pass situations to share these cycles.

#9: Explore the Chicago Pedway System

It’s obvious the city caters to pedestrians and this tradition dates back to pre-World War II when construction of the Chicago Pedway System began. Spanning over 40 city blocks north-and-south, navigating this expansive underground walkway includes admiring the artwork, dining at restaurants and shopping.

It started as a way to escape the chilly winter winds with a subterranean pathway connecting the L-train stations together. Today, it’s an interesting and eclectic way to get around town and avoid vehicles on Chicago’s busy streets. 

#10: Get in Touch with Mother Nature

Indoor greenhouse Chicago

Source: Enjoy Illinois

There are plenty of ways to enjoy the great outdoors and get in touch with Mother Nature in this region of Illinois. One of the many places worthy of a visit include the Peggy Notebaert Nature Museum or more of the outdoors can be found inside at the Garfield Park Conservatory

Along with these venues, there are dozens of pristine parks to explore in the Chicago City Park system. Check out their website to locate the outdoor venues you’d like to visit and experience. 

#11: Check Out Navy Pier

Chicago navy pier

Source: Navy Pier

At the Navy Pier, there’s so much offered at this multifaceted visitor attraction it’s worthy of its own guide of things to do on a weekend in Chicago. The pier extends over the water for six city blocks covering 50 acres including a home for the Crystal Gardens, Chicago Children’s Museum, an IMAX theater and more.

Part of the pier is drenched in a carnival atmosphere, with their Funhouse Maze, amusement rides including the enormous Centennial Wheel suspending riders over two-hundred-feet in the air while lighting up the Chicago skyline at night.

Since there’s so much to see and do on the boardwalk, why not turn it up a notch and plan a whole day affair? Start by booking a Navy Pier Signature Food Tour in the afternoon, stay and play on the pier followed by a presentation from the Chicago Shakespeare Theater. Talk about dinner and a show, what a fantastic way to spend a full weekend day and night on the Chicago shoreline.

#12: Watch a Shakespearean Play

Navy Pier Shakespeare Play

Source: Navy Pier

The Navy Pier also hosts the Chicago Shakespeare Theater (or CST for short), the largest performing arts venue in the Windy City. Along with classics penned by William Shakespeare like Hamlet, Macbeth, Romeo, and Juliet, CST also presents light-hearted musical favorites for kids of all ages like Bedknobs and Broomsticks or the high-flying adventures of Peter Pan.

This non-profit production company and location have helped to keep Chicago on the cultural map since 1999 winning multiple Laurence Olivier Awards and a regional Tony Award in 2008 with up to 600 presentations annually.

#13: Visit the Top Museums in Chicago

Chicago graffiti

Source: Pexels

With more than three dozen museums to visit in the city, it’s hard to know where to start. You might want to begin by exploring this list highlighting dates, times or conditions when you can visit these amazing venues free of charge. This roster also includes the Lincoln Park Zoo which is open to the public year-round without paying for a ticket along with information about the other zoos in Chicago.

There’s also no charge to visit less than traditional locations like the Busy Beaver Button Museum and outdoors at the Chicago Botanic Garden. More classic venues are open for a small charge to cover expenses and donations are always encouraged at the following spots:

#14: Experience The Magnificent Mile

Magnificent Mile Chicago

Source: The Magnificent Mile Facebook

This eight-city-block stretch of the neighborhood running through the central part of Chicago runs up-and-down Michigan Avenue and given the lengthier title of The Magnificent Mile. Either on the street itself or a stone’s throw from this arterial avenue in Illinois, there are 275 restaurants and more than 460 retailers located here with well-recognized brands like Disney, Nike, Zara and more to explore.

#15: Hop On the Chicago Crime Tours Bus

Many are aware Chicago was once the stomping ground for many notorious gangsters often referred to as The Untouchables during the prohibition era in the United States. One of the Chicago Crime Tours buses will take riders to get a first-hand look at locations related to the dealings of big mob names like Al Capone, John Dillinger, Frank “The Enforcer Nitti, and more. The tour also makes a stop at the site of the St. Valentine’s Day Massacre, one of the bloodiest murders in American history.

#16: Listen to Live Jazz and Blues Music

Chicago jazz clubs

Source: Pexels

The namesake musical movie Chicago was a smashing success raking in over $300 million dollars globally. The city is world-renown for its historic blues and jazz roots with a few of the most notable venues worthy of visiting include:

  • Buddy Guy’s Legends – Founded in 1989 by this blues veteran, he still plays a series of performances in January.
  • Green Mill Cocktail Lounge – Run by mobsters during days of prohibition, this lounge still highlights Al Capone’s favorite booth.
  • Kingston Mines – Dating back to 1969 at its Lincoln Park location, the shaft showcases two live performances every evening.

There are over 200 live music venues available along with some of the nation’s favorite music festivals. Both free and ticketed, every year the Chicago Jazz Festival, Lollapalooza and Pitchfork presentations are highly-anticipated annually. 

#17: Soak Up Stunning Views from the Willis Tower Sky Deck

This Chicago landmark was once known as the Sears Tower and formerly held the title of the tallest building in the world for more than two decades. Renamed the Willis Tower, The Ledge Experience on the Sky Deck is simply stunning. En route to the elevator, visitors will watch a short movie, meander through museum-quality exhibits while learning about the history of this building along with other architectural wonders unique to Chicago.

After a brisk ride to the 103rd floor, the Sky Deck along with four, glass-paned viewing rooms extend out over the city below. These platforms aren’t for the faint of heart showcasing a sheer drop of over a hundred feet above the streets.

Skip the lines by purchasing a fast-pass ticket online. Be prepared to literally step up and witness the amazing views of four surrounding states stretching out nearly 50 miles over the Chicago skyline.

#18: Check Out Chinatown

Chicago chinatown

Source: Enjoy Illinois

Cities like San Francisco are famous for their heavily Asian-influenced neighborhoods and Chicago is also host to a charming Chinatown section of this town. For lovers of oriental cuisine, this area is a Dim Sum paradise along with many spots to enjoy barbequed pork and other classic Chinese favorites. Touring the region will take about 40 minutes often with specials running daily especially around lunchtime.

Bonus Travel Tip: Chicago’s Chinatown is one of the most dynamic, diverse, and delicious neighborhoods in the city. Check out this guide to help you navigate its hundreds of eateries, unique shops, and historic landmarks so you have an authentic, local experience. You’ll find some of Chinatown’s most intriguing cultural sights, mesmerizing annual events, and superior culinary spots. Head here to discover the 21+ amazing restaurants, stores, and landmarks that only locals know about (and tourists totally miss!). 

#19: Relax at the Alfred Caldwell Lily Pool

Chicago lily pool

Source: Pexels

Named after its creator, the Alfred Caldwell Lily Pool is part of the Lincoln Park Conservancy constructed back in the 1930s in a pristine Prairie style. The pool is lined with winding stepping-stone paths, slabs of limestone, circular benches, surrounded by plants native to the Midwest and is home to a beautiful waterfall. This is a wonderful place to relax and unwind after a long week of work or school.

#20: Catch a Performance at the Chicago Theatre

Source: Chicago Theatre Facebook

Part of the Madison Square Garden family, the Chicago Theatre is an iconic part of the downtown district and is often featured in movies filmed in this city. The picturesque marquee and vertical sign are worthy of a snapshot even if you won’t be attending a show. Attendees enjoy live performances from comedians, world-class musicians, dance companies and lectures by renowned cultural figures.

Schedule a tour to learn more about this historic theatre with its beautiful central arch that mimics the false-perspective effect of the Palazzo Barberini in Rome and is glazed with Tiffany stained glass. It’s a stunning sight and dramatic location both inside and out that’s worthy of visiting.

#21: Listen to the Symphony

Similar to the theater, the Chicago Symphony Orchestra is an important part of the cultural and performing arts scene in Illinois. Consistently hailed as one of the greatest orchestras in the world, this National Historic Landmark was constructed in 1891 on what is now South Michigan Avenue. The venue is comprised of the Grainger Ballroom, Buntrock Hall and the 2,522-seat Orchestra Hall all housed inside this complex.

Ticket prices are affordable starting at just $30 to watch and hear some of the world’s top soloists, top talented musicians, and guest conductors. One of the most preeminent conductors of his time, Riccardo Muti became the 10th musical director of the symphony in 2010.

#22: Tour Wrigley Field

Chicago cubs wrigley field tour

Source: Pexels

Planning a weekend activity in Chicago should always include contemplating a visit to the home of the Chicago Cubs and the second oldest ballpark in America. Well-known for its ivy-covered walls, watching a game unfolding in this classic coliseum is on many sports enthusiasts’ bucket lists.

Tours of the stadium at Wrigley Field are available on select game days and other times when there are no ball players competing on the baseball diamond. Depending on the date, tours generally include sites occurring on:

  • On Game Days: Visiting the seating bowl, press box, bleachers, indoor batting cage and an opportunity to step out onto the field. On game days, tours will not include entry to the clubhouses. However, visitors will enter the ballpark before the gates are open to the public for an immersible experience before the competition begins.
  • On Non-Game Days: Tours when the players aren’t in uniform usually include the aforementioned with bonuses of checking out the visitor’s and Cubs’ clubhouse, the dugout, and walking on the field. 

The tours begin in March along with the start of the baseball season and run through September. They’re a unique way to learn about the storied history of Wrigley Field while observing the grounds from the best behind-the-scene views available both inside and outside the stadium. In closing, here’s hoping you have a fantastic weekend whatever you’re planning to do.

Connect With Chicago Food In Unexpected Ways


Enjoy the Best in Chow Food Tour on TripAdvisor’s #1 Rated Chicago Activity.

Skip the lines & eat iconic Chicago-style dishes in River North and Streeterville.

Offered daily; Includes Chicago-style hot dog, Italian beef and deep-dish. 


$60 Adult Tickets (Food Included)
3 Hours; VIP & Child Tickets Available

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