Everything Fun You Can Do in Chicago This Weekend

By David Bolaños on Apr 06, 2022

Chi-town, the ‘windy city’, and ‘city of the big shoulders’ are just three of the ways that the infamous city of Chicago is otherwise affectionately known. And while the names don’t necessarily allude to it, Chicago events are like no other city in America.

Located in the North East of the US, its population are known for their deep dish pizzas, sports-crazy culture and being the home of the blues. Plus, with the Chicago river situated right on Lake Michigan, beautiful natural surroundings are right on the edge of the doorstep.

But as the third-largest city in America, Chicago is also well-built for entertaining tourists in all manner of activities. Those looking specifically for a two-day Chicago itinerary need look no further to plan every single minute of their trip. However, many of the best things to do in Chicago this weekend actually don’t require much planning at all.

In this guide, you’ll learn how to navigate the city, as well as 11 of the best things that you can spend your time on this weekend in Chicago.

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Join a community of like-minded people who live, work, and explore on their terms at Selina Chicago!

How to get to Chicago

Before getting into things to do in Chicago, it’s important to give the city some context. Chicago has some little-known quirks that travelers won’t find in other cities, which are good for tourists to know before they reach the Chicago riverwalk.

International travelers or those coming from a distance will likely arrive at Chicago O-Hare airport, which is currently among the top 10 busiest airports on the entire globe. After navigating to the way out, there are several options to get into the downtown area;

  • Train
  • Bus
  • Shuttle
  • Taxi


Taking about 45-minutes, the train is an easy option and only costs about $5. Simply take the blue line “L” train at any time of day (the train runs on a 24-hour schedule) and arrive in downtown Chicago.


The bus is another good option for those who aren’t in a rush and don’t mind following the schedule of the public transportation. This is also the most economical option, which can be hugely beneficial for patrons on a budget.


Want to get from the airport straight to your hotel and accommodation? A shuttle will get adventurers from A to B in the comfiest and most secure way, with more privacy than standard public transportation options. Get in touch with us to book your shuttle service at a time that suits you.


With both standard taxi and rideshare options such as Uber, travelers are not stuck for options when they reach Chicago. Of course, the benefit to this option is higher privacy and security around your travel, which comes at the cost of a much higher charge. Expect to pay a minimum of $40 to reach the magnificent mile downtown area from Chicago O’Hare International airport.

Where to Stay in Chicago

As you’re about to learn, there are a ton of fun things to do in Chicago. However, where travelers decide to stay in the city can change their entire experience. The different neighborhoods have hugely different environments and are therefore each well-suited to a different type of traveler.

Fortunately, we’ve published a lengthy guide specifically to help travelers learn more about choosing where to stay in Chicago. But here’s a quick summary:

There are five Chicago neighborhoods to consider.

  1. The Loop
  2. River North
  3. Gold Coast
  4. Wicker Park
  5. Magnificent Mile

The Loop is the most central area with many businesses and corporations. The types of travelers who best thrive here are those who want to be right in amongst the heart of the action.

River North is perfect for tourists who want to prioritize nightlife. The area is well-known as the best party district in the city, and offers a huge range of after-dark bars and clubs.

Gold Coast is a very high-end luxury district filled with designer boutiques and Michelin-starred restaurants. Boujee travelers will enjoy this district the most.

Finally, Wicker Park is widely considered the ‘trendiest’ neighborhood in Chicago, with a vibrant hipster feel. It’s home to the music scene in Chicago and would be ideal for the alternative crowd.

About Magnificent Mile

In our humble opinion, the best places to stay in Chicago are located in Magnificent mile. With its more upmarket feel, most people tend to feel safe in this area. In terms of things to do in Chicago, those who stay in this district are centrally located and benefit from easy access to shops and restaurants.

Fortunately, this is where the Selina Chicago is located and will put holidaymakers in one of the best positions to explore all areas of the city.

Selina Hotel Chicago


(on the map Selina Chicago)

Best things to do in Chicago this weekend

Depending on the type of weekend, there are plenty of different ways to spend time in Chicago. Some of the best restaurants in the country are located here, and there’s also a mecca of upmarket stores and shops.

In this guide, we’re focusing on some out-of-the-ordinary activities that are specific to Chicago city, however. While shopping is available everywhere, attractions such as ‘the bean’, ‘Skydeck’ and Lake Michigan are not. Without further ado, let’s get into the best things to do in Chicago this weekend.

Catch a Chicago Blackhawks Game

When it comes to Chicago events, sports might be the first thing that comes to mind. And there’s nothing more Chicagoan than the Blackhawks! Six-time Stanley Cup winners, the Blackhawks are the city’s premier ice hockey team and totally rule the ice most seasons.

Visitors can find home matches at the United Center, and games can last up to 3 hours, considering time for breaks and intermissions. Games occur most weekends (as well as once midweekly) throughout fall to spring, with the official season beginning in October and finishing in April. Expect to pay around $30 per ticket.

Attend to experience the rush of ice hockey and become merged with the true locals in their favorite tradition. The atmosphere inside the arena is usually electric, and there are plenty of chants and cheers to get involved with. Make it a full day out by grabbing a hotdog or fries from a local vendor, too.

Sunbathe at Oak Street Beach

Oak Street Beach is one section of the 26 miles of shore in Chicago, lining the entry point to Michigan Lake. Found in the Gold Coast neighborhood, it’s a simple six-minute taxi ride North of downtown Chicago.

Fortunately, Oak Street Beach is one of the best free things to do in Chicago, since access to the public costs nothing. There are plenty of amenities at the site, including volleyball nets, restaurants and public restrooms.

Visitors can spend an entire day at the beach, taking in the sunshine and splashing around in the water. Just be sure to bring plenty of water and stay hydrated, as the weather in Chicago reaches an average of 85F.

Attend a Gig at Metro

For the more indie travelers among us, Metro Chicago is a historic music venue found only a stone’s throw away from Wrigley Field. On the weekends, attending a gig at metro can be one of the most fun things to do in Chicago Illinois.

In Spring 2022 alone, Metro is hosting the likes of Holly Humberstone, Slowthai, Don Bronco and Mall Grab- talk about diversity! But this isn’t just one of your usual ‘things to do in Chicago’, Metro’s history as a music venue is like none other.

Opened in 1982, its first year of business saw musicians such as REM, Depeche Mode, Billy Idol and The New Order through its doors. Cemented in Chicago culture, it’s not one to be missed.

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Join a community of like-minded people who live, work, and explore on their terms at Selina Chicago!

Take in the Views on SkyDeck Chicago

Nobody can walk around central Chicago and miss the huge 110-story building of Willis Tower. Located in the Loop district, the SkyDeck gives 360-degree panoramic views of the entire city. On a clear day, this means views for miles and miles.

When considering Chicago things to do, the SkyDeck is a staple. Glass boxes extend outside past the typical ‘ledge’ of the building, giving visitors the chance to look down onto the city below from hundreds of meters in the sky.

Opening hours are pretty standard, with entrance available between 9 am-10 pm on Sundays to Fridays and half an hour earlier on Saturdays.

The entry price is approximately $36. However, those who want to make the most out of their trip might prefer a Chicago citypass, which encompasses entry to a range of tourist attractions like this one, and:

  • Chicago history museum
  • Field museum
  • Shedd Aquarium

Find a Festival

Fortunately, every season is festival season, meaning travelers can never run out of things to do in Chicago. Visitors in Winter get to experience Christmas-themed yuletide festivities, while summer vacationers might want to seize the opportunity to attend a Chicago Pride fest.

Here are some of the best weekend festival Chicago events each month this year:

  • January: Ice Skating Festival
  • February: Chinese Lunar New Year
  • March: St Patricks Day
  • April: Chicago Restaurant Week
  • May: Mayfest
  • June: LGBT Pride
  • July: Lollapalooza
  • August: Chicago Triathlon Festival
  • September: Pitchfork Music Festival
  • October: Chicago Marathon
  • November: Christkindelmarket Chicago
  • December: Winterland (Gallagher Way)

So, those looking for things to do in Chicago this weekend won’t be hard-pressed to find a festival that suits them.

Devour a deep-dish pizza

Chicago’s deep-dish pizza style is rooted in deep history and tradition. It’s not just another of the fun things to do in Chicago, the deep dish pizza is a reverse on a classic, with tomato sauce on top of the mozzarella to keep all of that cheesy goodness alive inside.

This lip-smacking dish can sometimes be described as a pie with its super thick crust, and there are eligible vendors all over town. Some of the best places to find a slice in Chicago include Pizano’s, Burt’s Place and The Art of Pizza.

However, we suggest you don’t stop there. Food lovers will likely prefer to embark on ‘a pizza tour of the town’. After all, it’s probably the best way to get to know Chicago.

Visit the Bean

Did you know that Cloud Gate is the official name for the huge mirrored sculpture found in Millenium Park, otherwise affectionately known as the Bean? Officially launched into the city in 2004, its worldwide global fame and success have made it one of the best things to do in Chicago.

The bean was designed and made by Anish Kapoor, a sculpture specializing in conceptualism and installation artworks. Its mirrored effect comes from the materials: the bean is made from sheets of stainless steel that have been seamlessly welded together to create a smooth surface all the way around.

Visiting the bean is one of the many free things to do in downtown Chicago, and can take just five minutes to snap a picture. Or, combine it with some other sightseeing in order to brush up on some Chicago landmarks and history knowledge.

Support the Chicago Cubs at Wrigley Field

If major league baseball is more your thing, then checking out the Chicago Cubs will probably be at the top of your list for things to do in Chicago this weekend. The season runs from early April through to early October, and 30 teams compete for the winning trophy.

Wrigley Field is located on the Northside of Chicago and is the second-oldest baseball field in the entire country. Even better, the Cubs’ huge rivalry with Chicago White Sox means that games are highly intense, competitive, and very exciting. Attending a game is one of the more ‘proper Chicago events’, where tourists can mix with locals and take in the atmosphere

Expect to pay approximately $83 on average per ticket, and plan for around 3+ hours at the match. Fortunately, there are a number of different food vendors and other amenities that make this one of the easiest, fun things to do this weekend.

Go on a free street art walking tour

When the thought of Anish Kapoor’s sculpture gets the brain whirring, why stop at the bean?

Street art has a long history in Chicago, originally appearing solely as ‘tags’ in the 1980s. However, it has now evolved into the delicate expression of the artists who create, and a street art tour can be one of the popular things to do in Chicago this weekend.

Wicker Park and Pilsen are two Chicago neighborhoods with a particular affinity for contemporary art. As gentrification has increased in these two areas, street art has been used to give a realistic insight (and natural history) into the lives of the general public. Therefore, street art tours are Chicago activities for tourists who are looking to understand more about the culture in Chicago.

Most of the street art tours in Chicago are free or ‘pay as you feel’. This means that tourists can simply tip the guide at the end of the tour in order to thank them for sharing their knowledge and highlighting the best spots in town.

Cruise over Lake Michigan

How could we discuss all the things to do in Chicago Illinois without highlighting one of only five great lakes in all of America, Lake Michigan? The lake, which is home to all manner of wildlife and creatures, has its own ecosystem of fishermen and tourism like any other seaside resort.

Fortunately, that means that many visitors enjoy a cruise, which presents the best that Lake Michigan has to offer. Head to Navy Pier, where there’ll be river cruises around architecture, sightseeing and fireworks. Adventurers can even hop on a speed boat for some high-speed action and a thrill or two.

Chicago is pretty good at doing romance, too. Those visiting Chicago with a partner are likely to prefer a lunch or dinner cruise along the river.

Tour the breweries

Inquiring about fun things to do in Chicago for adults? A brewery tour should fit the bill. The current craft beer scene in Chicago is seeing explosive growth in the past decade or so, and the city now has more breweries than any other city in America.

Honestly, it’s pretty hard to recommend just one Chicago brewery to visit, since there are so many options, each with their own unique attractions. But, some of the most well-known include Lagunitas and Half Acre Brewing Company.

It is recommended to arrive early and know that ‘first come, first served’ may mean hours in waiting. Beware that these tours are incredibly popular with the local population, too. In fact, those really wanting to ‘live like a local’ can check out tons of other non-touristy things to do in Chicago, too.

Selina Chicago

Join a community of like-minded people who live, work, and explore on their terms at Selina Chicago!

Chicago FAQs

  • When is the best time to visit Chicago?

    The best time to visit Chicago is likely in Spring or Fall, on either side of the summer.

    To avoid mass tourists in places like Grant Park, spend the months of June, July and August elsewhere. However, to still make the most of good weather and tick off all the Chicago activities on the list, we recommend visiting Chicago in the months of April, May, September or October.

  • Things to do in Chicago when it rains?

    Hopefully no one is surprised to know that there are still so many fun things to do in Chicago, even when it rains. In fact, simply grab a waterproof jacket and head to any of the places on this list. Those wanting to stay indoors might prefer to go to a museum, or explore one of the many local art galleries.

  • What to do in Chicago in winter?

    Fortunately, Millennium Park hosts an ice skating rink for three months across the Winter from November to January. It’s one of the best Chicago events to attend in winter and visitors can actually go every single day, not just on the weekends.

    Alternatively, some Chicago hotels offer tourists the chance to play the winter olympic sport of curling; which involves sliding heavy stones towards a target on a sheet of ice. Lincoln Park Zoo is also open all year round.

  • Things to do in Chicago when alone?

    Just because you’re alone in the city, doesn’t mean there’s no fun to be had. In fact, there are plenty of Chicago things to do for individuals and solo travelers. Meet other adventurers at Selina, which is highly rated among solo travelers, and choose group tours around the local area to connect with others.

    Or, explore the city on your own terms by attending gigs, Chicago theatre, and galleries like the art institute by yourself, the way you want to.

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