Before heading out-and-about to enjoy all the happenings, check out this guide to our favorite 22 things to do this weekend in Chicago.
There’s no shortage of fun things to do in Chicago. We help you narrow it down with our favorite 22+ things to do this weekend in Chicago.
Catch the next rising star at Chicago’s famous The Second City and then brag to your friends when you catch them on the big screen.
Plenty of legendary comedians come from Chicago, including Saturday Night Live alumni John Belushi, who was born here. The Animal House star used to perform at The Second City on Wells Street as did Dan Aykroyd, Tina Fey, Steve Carell, and Amy Poehler – just to name a few.
Tickle your funny bone this weekend with unique improv performances, hilarious sketches, special guest appearances, and more.
Source: Flickr
Chicago is world-famous for deep-dish pizza, hot dogs, Italian beef sandwiches, and so much more. To discover these big bites and bold flavors, book a food tour in Chicago. These delicious journeys let you sample some of the best food in the city in only three hours:
If any or all of these routes have your taste buds tantalized, be sure to snag tickets now. Bring your friends, bring your family, but most importantly, bring your appetite! Food tours make a great gift or way to commemorate a special occasion like an anniversary, graduation, or birthday.
Source: Chicago Food & City Tours
Hunger in the West Loop is… not a thing. We’re incredibly lucky to have some of the greatest restaurants in the city all within walking distance.
Randolph Street, aka Chicago’s Restaurant Row, is home to multiple star-rated Michelin restaurants, like Girl and the Goat and Next. There are also more attainable spots that are 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 a deep dive into the West Loop’s renowned and extensive food and restaurant scene. You’ll hit up a hip food hall, artisan chocolate shop, a Chicago outpost of a legendary Roman pizzeria, and more!
Source: Pexels
Take some epic selfies and group shots with the highly Instagram-able Cloud Gate sculpture at Millenium Park. Also known as “The Bean” (but don’t say that around its artist Anish Kapoor), this epic public sculpture has been delighting tourists and locals alike since 2006.
Ready for some fun facts?
The Cloud Gate is covered with 168 seamlessly joined stainless steel plates. It measures 33-feet high, 42-feet wide, 66-feet long and weighs around 110 tons. Its rounded design gives you the perfect reflection of the beautiful Chicago skyline. Now, you’ll be prepared to really wow your friends and family when you take them to this emblematic part of the Chicago landscape.
Get up close and personal with a giant Picasso!
Another opportunity for a spectacular snapshot is located in the Daley Plaza where the Chicago Picasso has stood since August 15, 1967.
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.
Make a splash at the Buckingham Fountain in Grant Park, located right in the Chicago Loop.
Constructed in 1927 from Georgian pink marble, it’s one of the largest fountains in the world. It features 200 jets shooting streams over statues more than 25-feet tall across a pool nearly 300-feet in diameter.
After the sun sets, gorgeous lights illuminate this monument making it the perfect setting for some picturesque photo ops.
Photo Source: Pexels
Explore the Chicago by way of the river on The Riverwalk. This feat of urban planning cuts through downtown and offers many fabulous views of the city above. While traversing this trail, you’ll be treated to stunning public artworks and sweeping views of the skyline.
There are numerous bars and restaurants situated on The Riverwalk that make for a great stop while trekking through the city. Be sure to have your camera ready for selfies in front of some of Chicago’s most iconic buildings!
Options to travel on the river itself include water taxis, boat tours, or DIY journeys on an urban kayak or cycle boat. Many riders take Chicago’s floating taxis to travel from one waterfront tourist location to another.
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 will soak in the Chicago skyline or stroll along the shoreline on a leisurely day off.
You can also use the path to reach the South Shore Cultural Center, the Shedd Aquarium, or Navy Pier. To get around faster, there are bike and scooter rental stations along the way with some offering day pass situations to share these cycles.
So hop on a bike or lace up your running shoes and take in the lakefront like a local!
Really go “down” town with Chicago’s Pedway System.
It’s obvious the city caters to pedestrians and this tradition dates back to pre-World War II when construction of the underground Chicago Pedway System began. Spanning over 40 city blocks north-and-south, when you navigate this expansive subterranean walkway, you’ll get to admire artwork, underground dining, and even shopping.
It started as a way to escape the chilly winter winds and today, it’s an interesting and eclectic way to get around town and avoid vehicles on Chicago’s busy streets.
Source: Enjoy Illinois
There are plenty of ways to enjoy the great outdoors and get in touch with Mother Nature right without leaving the city! One of many places worthy of a visit includes the Peggy Notebaert Nature Museum or more of the outdoors can be found inside at the gorgeous 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.
Source: Navy Pier
At the Navy Pier, there’s so much offered that 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. It’s home to the world’s largest rooftop bar (Guiness certified!), Chicago Children’s Museum, a Tony-award winning theater, and more.
Part of the pier has a carnival atmosphere, with their Funhouse Maze and amusement rides, like the enormous Centennial (Ferris) Wheel suspending riders over two-hundred-feet in the air while lighting up the Chicago skyline at night.
Even better?
Visitors can now stay on the Pier itself at the Sable Hotel. Book your stay today!
Source: Navy Pier
The Navy Pier also hosts the Chicago Shakespeare Theater (CST for short), the largest performing arts venue in the Windy City. Along with classics penned by William Shakespeare, CST also presents light-hearted musical favorites for kids of all ages, world-premiers of new shows, and hosts international theater companies.
This non-profit production company have helped to keep Chicago on the cultural map since 1999. It has won multiple Laurence Olivier Awards and a regional Tony Award in 2008.
Source: Pexels
With more than three dozen museums to visit in the city, it’s hard to know where to start. Start by exploring this list highlighting dates, times, and conditions when you can visit these amazing venues free of charge. This roster also includes the Lincoln Park Zoo, which is always open to the public, free of charge.
There’s also no charge to visit less than traditional locations like the Busy Beaver Button Museum and outdoors at the Chicago Botanic Garden, located in the Northern burbs. Willing to pay for a great cultural experience? Check out one of the museums below:
Source: The Magnificent Mile Facebook
Want to shop ’til you drop? Then, head to this stretch of Michigan Avenue called “The Magnificent Mile.” Either on the street itself or a stone’s throw from this arterial avenue in Chicago, there are 275 restaurants and more than 460 retailers, from brands like Disney, Nike, Zara to the second largest Starbucks in the world. Whether you’re looking to window shop or drop some dough, head downtown to the “Mag Mile.”
Chicago was once the stomping ground for many notorious gangsters, often referred to as “The Untouchables,” during the prohibition era in the United States. Chicago Crime Tours buses will give you 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.
Source: Buddy Guy’s Legends
The Windy City is world-renowned for its historic blues and jazz roots. Take in the music at these legendary venues:
There are over 200 live music venues along with some of the nation’s favorite music festivals. Every year, thousands of visitors come to the Chicago Jazz Festival, Lollapalooza, and Pitchfork. Check out the lineups and catch your favorite acts in your new favorite city!
This Chicago landmark was once known as the Sears Tower and 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, you’ll make it to the Sky Deck where there are with four, glass-paned viewing rooms that extend over the city below. These platforms aren’t for the faint of heart: you’re 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.
Check out our Buildings and Bites tour as well if you’d like to check out the Willis Tower along with other iconic Chicago buildings.
Source: Enjoy Illinois
Did you know that Chicago has a vibrant and bustling Chinatown? Get your dim sum brunch on or enjoy other favorites like barbequed pork, hand pulled noodles, egg tarts, and boba tea. Tours of both the old and new sections of Chinatown will take about 40 minutes and specials can often be found, 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. Head here to discover the 21+ amazing restaurants, stores, and landmarks that only locals know about (and tourists totally miss!).
You can also join us on our Chinatown Adventure food tour and let us show you our favorite Chicago institutions and off-the-beaten-path finds!
Source: Pexels
The Alfred Caldwell Lily Pool is part of the Lincoln Park Conservancy and was constructed in the 1930s in a pristine Prairie style. The pool is lined with winding stepping-stone paths, circular benches, and is surrounded by plants native to the Midwest. This is a wonderful place to relax and unwind after a long week of work or school. Who knows, you might catch a glimpse of a wedding ceremony happening in front of the beautiful waterfall.
Source: Chicago Theatre Facebook
Catch a concert or a comedy show at one of the most Instagram-able venues in the city, the Chicago Theatre. 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.
Want a backstage pass?
Tours of the historic venue are a great way to get up close and personal with the grand architecture and give you a chance to pretend to be a rockstar.
Chicago Symphony Orchestra is consistently hailed as one of the greatest orchestras in the world. Hear them live in their historic home on Michigan Avenue. The venue is a National Historic Landmark and was designed by famed architect Daniel Burnham.
Ticket prices are affordable starting at just $30 to watch and hear some of the world’s top soloists, 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.
Source: Pexels
Knock it out of the park at the “Friendly Confines.” Take a tour of the home of the 2016 World Series champs, The Chicago Cubs. Wrigley Field is second oldest ballpark in America and its ivy-covered walls and old-fashioned score board are legendary.
Tours of Wrigley Field are available on select days. Depending on the date, tours generally include sites occurring on:
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-scenes views.
In closing, here’s hoping you have a fantastic weekend whatever you’re planning to do.
This tour is complete with treats from 6 bakeries, stories of ethnic holiday traditions, & ample shopping time to purchase additional goods.
Savor Chinatown with a full immersion into the culinary & ethnic pageantry at five authentic, mouthwatering restaurants
Subscribe to our newsletter!
