20 Amazing Things To Do In Chicago On Weekend

1. Catch A Broadway Show

The Loop boasts all the theaters in Chicago and more, so save yourself the time of traveling by staying in this part of the town for your next night out. Shows such as Harry Potter and the Cursed Child, Back to the Future: The Musical, or even The Book of Mormon are currently wowing audiences with what seems to be giving everyone a bit of something.

Not only that, but many theaters like the Cadillac Palace and CIBC Theatre are just steps away from local attractions or public transportation. And of course, you should also enter the digital lottery for a chance to grab some discounted tickets, so it won't cost an arm and a leg.

2. Explore The Magnificent Mile

The Magnificent Mile is the heart of Chicago, with diversities that allow for a meandering trip for the weekend (of shopping, dining, or entertainment). This iconic strip runs along North Michigan Avenue, making it ideal for those who want to make the most of their time in one place.

Have breakfast at the world's largest Starbucks and go shopping in exclusive, high-end, and unique boutiques. Interactive family fun awaits at the Chicago Sports Museum, and visitors to 360 Chicago can stop at the breathtaking observation deck with stellar skyline views.

Cap off the day with dinner at acclaimed Chicago restaurants like Lou Malnati's for deep-dish pizza.

3. Visit Navy Pier

Activities near Navy Pier make it one of the best tourist attractions in Chicago. This place is abundant in things that one can enjoy with its beautiful views of Lake Michigan and the city skyline.

Just hop on the Centennial Wheel for some of the most incredible views you'll find, explore interactive exhibits at the Chicago Children's Museum, or see a live show from the Chicago Shakespeare Theater.

Live on the Lake concert series to free outdoor movies that will keep you coming back all summer long, Navy Pier is keening throughout every weekend.

4. Take A Ride On The Chicago Water Taxi

Hopping on the Chicago Water Taxi has got to be one of the top fun activities in Chicago, where you get two of the most crucial elements of travel: time-saving and enjoyment.

The vivid yellow boats speed down the Chicago River, connecting hotspots such as Michigan Avenue, Ogilvie Transportation Center, and Chinatown. Just picture yourself gliding alongside beautiful buildings and colorful communities without the obstruction of traffic.

With a unique perspective from the water, it is a great way to spend an otherwise lovely weekend. On top of that, the water taxi service switched to seven, making it more accessible than ever.

5. Try Chicago-Style Deep Dish Pizza

If you are planning activities in Chicago, then one of the things that would be on your list is eating deep-dish pizza. This rich, gooey treat is well entrenched in the culture of this region and gives just enough energy after a long day walking around all there is to see.

What's even luckier is that several of the best deep-dish pizza joints are near key top attractions in Chicago. So, for instance, Lou Malnati's is a chain that has spots all over the city.

So once you've ridden the Ferris wheel or seen a show at the Chicago Shakespeare Theater, stop into Lou's for what may be one of the best buttery crusts, topped with gooey mozzarella and tangy tomato sauce.

6. Attend A Music festival

Looking for a weekend you will never forget, full of music, culture and excitement? Then consider Chicago, with its world-class music festivals. Perhaps the grandest of them all is Lollapalooza, a four day takeover that transforms Grant Park into a veritable sonic wonderland.

For those who prefer a more close-knit experience, visit the Chicago Blues Festival at Millennium Park for vibes and smooth tones that will rock your world.

The Chicago House Music Festival will cover all the bases with clean mixes spun by DJs from around the world at this free event that showcases traditional choirs and contemporary urban gospel artists in Millennium Park.

7. Admire Chicago From The Willis Tower Skydeck

Situated on the 103rd floor, the Skydeck affords sweeping views of up to four states in clear weather. The highlight is walking out onto one of the Ledge's glass bays, which project 4.3 feet from a side wall, making it feel as if you're floating over downtown Chicago.

Here, the iconic attraction has been entertaining its audiences with engaging exhibits celebrating Chicago's history and culture. Enjoy the views and have a meal at Kindling, which features a delightful menu along with a beautiful skyline.

The Skydeck is a convenient weekend longstop, worth seeing for both locals and tourists.

8. Stroll Through Millennium Park

If you are looking to put life aside from Chicago for a weekend, there is no better place than strolling around Millennium Park. It is an urban oasis with jaw-dropping art installations, art gardens, and events galore that will catch the fancy of every visitor.

In the summer, there are free concerts and some movie nights at the Jay Pritzker Pavilion in the park, which makes it an excellent place to meet up with friends or family. Get yourself a coffee from Momentum Coffee and take a leisurely stroll here, just basking in the ambiance that is this iconic Chicago site.

9. Photograph With The Bean

The masterpiece, formerly known as Cloud Gate, offers a near vision into the heart of this city with its lively downtown core. The shiny surface of The Bean also reflects the surrounding skyline as well as those who come to see The Bean itself.

Walk under the sloping brim of that sculpture and enjoy a new view. Take a couple of selfies, and also be sure to get pictures of the incredible city views from right out front at Millennium Park. After strolling around The Bean, head over to Millennium Park, where you can walk right down into it.

10. Attend The Art Institute of Chicago

In a city that is home to world-class art, the Art Institute of Chicago remains one of the top weekend destinations. Home to one of the oldest and largest art museums in America, it offers more than 300,000 pieces of architecture from across several millennia.

The institute is located near many other Chicago attractions, such as Millennium Park and the Magnificent Mile. You could easily cover your whole itinerary with these, as it would make a nice route to follow, especially if time was short.

Highlighting the museum's permanent capital are the works of masters such as Impressionists and Post-Impressionists like Monet, Renoir, and Van Gogh.

11. Witness A Live Show At Second City

This legendary comedy troupe has been keeping audiences in stitches since 1959. The Second City performs a new, high-energy show every weekend filled with fast and funny sketch comedy.

Newish revue titles like The Devil is in the Detours and Oh, the Places You'll Glow! are currently getting some good buzz for their amazingly smart writing and talented performers.

With tickets for Second City shows starting at only $26, they are an extremely affordable option if you're just looking to get a night out. Its performances are every Friday and Saturday night, so it is simple to carve out in your weekend plans.

12. Relax At North Avenue Beach

North Avenue Beach is a gem of Chicago hidden amidst Lincoln Park. Soaking in the sun on North Avenue Beach is one of the best things to do in Chicago Boasting spectacular cityscape vistas and all sorts of things to do on the weekend, it is your outdoor oasis not far from the urban center.

Even though it is just for the summer months, free beach yoga will kick off your day. It is a refreshing way to wake up your senses with the sound of Lake Michigan gently flowing into that slow current. Play beach volleyball with your friends, or rent a paddle board and try it out in the water.

13. Set Out For Wrigley Field & Wrigleyville

Wrigley Field and surrounding Wrigleyville make the perfect weekend vacation spot for Chicagoans and out-of-towners. The official stadium of the Chicago Cubs is part baseball stadium but also a year-round sanctuary for devotees.

Next to the field is Gallagher Way, which offers outdoor movie nights, fitness classes, and seasonal markets, a lively spot where you can relax. The Cubs are in the beginning of playing home games, and there will be fun concerts to catch, including Green Day and Pearl Jam this summer.

Not only that but local taverns and eateries provide scrumptious bites to eat, guaranteeing your weekend will be full of fun & flavor.

14. Root For Home Teams At The United Center

This legendary stadium plays host to the NBA's Chicago Bulls and the NHL's Chicago Blackhawks and adds a thrilling sense of camaraderie among fans, both young and old. You feel the buzz as you walk into the arena, standing row after row of fans in their respective colors cheering on all comers.

There's nothing quite as exciting and hair-raising as going out to catch any live outcome with your own two eyes. The United Center on the Near West Side is also just around the corner from some restaurants, making your stay in the stadium more fun.

15. Take A Helicopter Tour

For those seeking a memorable Chicago weekend activity, feel the gentle thrill of discovering what aerial tours in downtown Chicago have to offer. Heli Chicago offers multiple flights, a 30-minute introductory flight best for novices, as well as more extensive tours that run at least 45 minutes and travel over different portions of the city.

This way, you will not have to waste a lot of time traveling and instead focus on your adventure at the heliports nearby. Airborne tours are a trend that has become more popular as an increasing number of individuals continue to search for new experiences with the purpose of excitement and sightseeing.

16. Immerse Yourself In Nature At The Chicago Botanic Garden

The Chicago Botanic Garden is a quick weekend adventure, just a short drive from downtown. At 385 acres, the mesmerizing living museum consists of 28 unique gardens and four natural areas, creating a tranquil environment away from the everyday chaos of real urban life.

Leaning for stress-free walks through foliage, seasonal activities, and simply meditating over the aesthetic of Mother Nature is available to visitors. The tranquil botanical garden is home to more than 2.8 million plants, including vivacious floral displays and serene water fountains alike.

Do not miss the Chicago events such as gourmet cooking classes and wellness events this summer.

17. Take A Chicago Gangster Tour

One of the free things to do in Chicago during the weekend is this awesome Gangster Tour. This interactive walking tour allows you to learn about the dark history of Chicago with a visit back in time to the lives and lifestyles of some well-known mobsters, such as Al Capone and John Dillinger.

You will be accompanied by a guide who knows how to get around, and you can hear all about the key points when it comes to Chicago's criminal history. True crime fans will love this peek into Chicago's seedy past, so consider taking this on your next weekend tour on your summer list.

18. Delve Into The Escape Room

In these team-building puzzle games, one is tasked to piecemeal clues that unlock the ability to break free within a designated period. The Great Escape Room, situated smack in the middle of downtown Detroit, has several themes, like a Sherlock Holmes expedition for puzzle nuts.

On the other hand, The Escape Game Chicago has rooms that have won awards such as "Prison Break" and "The Heist," which cater to all ages. Outdoor escape experiences are fun things going on in Chicago that allow you to wander the streets of neighborhoods like Fulton Market while solving mysteries, which can be a fun adventure.

19. Participate In A Street Festival

Chicago street festivals bring this city to life in the summer and provide a destination for weekend wanderlust without going. Among the top Chicago weekend events is Wicker Park Fest, which brings more than 50 bands to play live music along with local food vendors and a bustling atmosphere that epitomizes the eclectic spirit of this colorful neighborhood.

At Do Division Street Fest, food trucks and shopping come together on a stretch that attracts legions of unique local vendors. Sample the local culture by visiting Fiesta del Sol in Pilsen, a celebration of Mexican heritage with food, music, and activities for kids.

20. Take A Bike Tour

One of the best ways to enjoy what Chicago has to offer while still outside is by taking a bicycle tour through the city. There is no doubt that it will make you vibrate with its atmosphere and vitality.

Between numerous bike paths running throughout downtown and scenic routes along the lakefront, Chicago is one of the country's most cycling-friendly cities, which means it is possible to visit sites like Millennium Park and Navy Pier without battling summer traffic.

Join a guided bike tour this weekend, where you will be shown places most people have never seen or known before and get to know the rich history of this city.