12 Unusual Things To Do This Weekend In Chicago

12 Unusual Things To Do This Weekend In Chicago

While seeing the amazing architecture and enjoying the river are definitely activities to cross off your bucket list, Chicago has a lot of unusual and interesting activities that should be added to your itinerary.

What is unusual about Chicago?

This exciting city is a classic America that is infused with a variety of foreign influences to keep people on their toes. You can enjoy a range of activities here that you wouldn’t ordinarily associate with the city.

Want to get out into the great outdoors, see the famous skyscrapers from a different angle, or feel like you’re in France on a wine trail?


Here’s how you can do all that and more in the city that never disappoints, with our guide on what to do in Chicago this weekend and weekends in the future.

Go On A Pullman National Monument Bus Tour

Pullman National Monument Bus Tour

This three-hour tour takes you through Chicago’s South Side where this national monument was home to thousands of people who worked for the Pullman Car Company in the late 1800s.

This community is filled with interesting landmarks and you’ll get to learn about its contribution to social equality of the 20th century.

For a quick bite of history, in the latter half of the 20th century, Chicago’s South Side was an industrial force with steel production and luxury trains being part of the city’s prosperity.

However, these industries sadly shut down.

Tours like this one aim to highlight the hard work and legacy left behind by the employees as it takes you on an interesting tour of the factories and landmarks of this once-prosperous company.

The tour, which lasts three hours, costs $40 for adults.

That really isn’t a lot if you consider that you’ll be seated in a luxury bus that has a restroom and provides you with drinks and snacks.

Enjoy A River Cruise

People On River Cruise

You can’t spend time in Chicago without seeing the Chicago River, which travels through the city in a system of canals and rivers and notches up an impressive 156 miles.

Instead of just seeing it, go on the Architecture River Cruise on the river.

This 90-minute tour gives you explanations of the history and construction of more than 50 buildings in the city, which is especially interesting if you consider that Chicago is the birthplace of the skyscraper.

This River Cruise has been named one of the best travel experiences in the world, and there are many things to enjoy about it, some noteworthy points being that the boats have open-air upper decks and full-service bars.

You will have to spend $45 for tickets per person on a daytime cruise, but there’s also a twilight cruise that costs $50.

Pay an extra $5 and you can enter the Chicago Architecture Center, where you’ll see a fantastic model of the city that has over 4,000 buildings as well as its Building Tall exhibit on the second floor that has supersized models of the city’s most beautiful skyscrapers.

It’s definitely a must-see before you leave.

Go On An Underground Scavenger Hunt

Scavanger Hunt

Ever wanted to explore the city’s underground world?

Now you can.

During an Atlas Obscura scavenger hunt, you’ll learn the history of Chicago’s Pedway, which lies in the heart of the city and connects buildings in downtown Chicago with underground passages and walkways over 40 blocks.

As Chicago residents will tell you, traveling underground is worth doing during the cold months to help you escape the freeze!

By participating in this underground scavenger hunt, you can learn how to navigate through the city underground in this fun tour that’s perfect to do with your friends. 

How it works

You’ll meet your host who’ll ask you 10 questions you’ll have to answer and these links to various Pedway locations.

You have to find the first location, write down the answer, and then move on to the next one.

The whole scavenger hunt will take about two hours, after which you can go watch a show or have dinner to reward yourself for your impressive skills, and it only costs $45.

Enjoy A Beer Tour

5 Rabbit Cerveceria

There are lots of beer tours in the city of Chicago, but one that’s a bit different from the rest is the 5Rabbit tour.

In case you don’t know, 5 Rabbit Cerveceria is the first brewery in the U.S. that’s Latin-inspired.

It’s all about using amazing and intriguing ingredients in beer, such as dulce de leche, lime peel, and chilies.

Take part in their Cotorreo Cervecero, or Beer Chat, a tour that takes place every second Saturday at their brewery.

It costs $25 per person and you can buy tickets in their online shop.

How the tour works is that you get a behind-the-scenes look at the brewery’s fascinating inspiration and how they craft their intriguing beers, and yes, you do get to taste three beers.

You also get a tour of the production facilities and will go home with a 5 Rabbit pint glass as a souvenir.

It’s a fun way to spend a lazy Saturday afternoon, so bring your friends.

Go On A Fireworks Helicopter Ride

This 20-minute helicopter ride takes off from S Halsted Street and takes you out over the Chicago skyline at night.

You’ll be amazed at how the city looks different at night, as you fly over landmarks in the city such as The Millennium Park, Lake Michigan, and the 360 Observation Deck.

To make the tour even more spectacular there are fireworks that you’ll be able to view from above for the first time ever.

Be sure to bring your camera as you’ll have amazing images that you’ll love to view again in the future.

This fireworks helicopter tour costs approximately $224, and it includes live commentary on board the helicopter, noise-canceling headsets, free parking, and all fees and taxes.

Embark On A Wine Trail

Lake Michigan Shore Wine Country

You don’t have to be a wine aficionado to enjoy this trip.

The Lake Michigan Shore Wine Country is a must-see.

It spans right across the southwestern area of Michigan and the vineyards are within driving distance of each other, so spend a day or two exploring them.

Then, to rest after a day of exploration, book yourself into a nearby hotel.

Castle In The Country is a bed and breakfast inn located in Allegan that’s perfect for some TLC – there are a spa and suites with whirlpool tubs and fireplaces.

As a bonus, it’s near to the winery towns of Holland and Kalamazoo, as USA Today reports.

A room in this inn will cost approximately $137 but it depends on the room you choose.

Go Hiking And Biking In Oglesby

Oglesby Illinois

One of the best things about the city of Chicago is that it’s a stone’s throw from other nearby attractions that are not to be missed.

If you love spending a peaceful time in nature or participating in outdoor activities, you must go to visit Oglesby.

This quiet town is located about two hours away from Chicago by car, perfect if you’re itching to do some outdoor activities, such as hiking.

The town of Oglesby is found near the Illinois and Vermillion River, and it is home to a variety of biking and hiking trails for people interested in a bit of heart-pumping activity outside.

Best of all, it’s close to two state parks: Starved Rock and Matthiessen, which makes it perfect if you’re spending time in Chicago for a day or two and want to go a bit further afield.

In Oglesby, you’re not limited to hiking and riding your bike – you can also enjoy a number of other activities, such as kayaking, rafting, and fishing.

Visit An Unusual Museum

The Art Institute Of Chicago

You might want to check out the museum staples in the city, such as The Art Institute Of Chicago, but there are loads of other weird and wonderful museums you need to visit.

Whoever said going to museums is boring or something reserved for school was sadly mistaken – or has never been to Chicago!

The city has a variety of interesting and unusual museums.

These include the Video Game Art Gallery. Here you’ll experience various exhibitions, depending on what’s on, such as the Pac Man History exhibition.

There’s also the International Museum Of Surgical Sciences that has medical artifacts such as amputation saws and displays of war wounds.

It sounds grim, but it’s very enlightening

If you love Saturday Night Live, make sure you check out The Museum Of Broadcast Communications that has various exhibits.

The museum also has an online museum store in which you can purchase memorabilia such as posters and DVDs of popular TV shows, radio encyclopedias, and stationary. 

For the various museums listed above, admission costs are as follows:

  • Art Institute of Chicago – Adults – $25, seniors, students, and teens – $19. It’s free for children and members.
  • Video Game Art Gallery – Free.
  • International Museum of Surgical Sciences – $17 for adults, but senior citizens, educators, students, and members of the military pay $13. Children between the ages of four and 13 pay $9.
  • The Museum of Broadcast Communications – $15 for adults, but senior citizens, students, educators, and military pay $12. Members get free admission.

Go Back In Time To Books & Records

Challengers Comics + Conversation

If you think bookstores and record stores are a throwback to previous years, that’s definitely not the case in Chicago.

There are loads of both of these to enjoy, so make it a throwback day and enjoy all the fun you can.

Don’t forget to visit Challengers Comics + Conversation where you can get fun comics to read that will make you feel like a kid again.

If you love music, check out Reckless Records.

You’ll find lots of music to explore, and sometimes there are even in-store performances to enjoy so ask them about their upcoming lineups.

If you love curling up with a good book, leave your digital reader behind and make sure you touch an actual book at Myopic Books, located in Wicker Park.

But, put your cell phone off as it’s not allowed. Don’t despair – this spot is perfect for unwinding with some great stories or attending a poetry reading.

Race Around The City In A Bike Tour

Chicago BikenRoll

If you want to see the city without stepping onto a bus or driving around in a rental car and you love riding your bike, a bike tour is perfect for you.

There are many tours you can enjoy on your bike around the city.

One that’s worth checking out is Bike ‘N Roll tours, which will take you through some of the hottest spots in the city, starting at the Navy Pier.

It’s the perfect combination of bike riding and seeing the sights.

Some of the landmarks you’ll see while pedaling include the Lincoln Park Zoo and Chicago Lakefront.

It’s two to three hours of fun and exercise, plus you can bring the kids along.

These bike tours run from April to December, and the cost for adults is $45 while kids under the age of 12 only pay $35.

Indulge In Unique Gelato

Black Dog

While you’re seeing the sights and enjoying yourself, don’t forget to stop and have a snack.

On a hot day, nothing quite hits the spot like gelato, but don’t limit yourself to the chocolate or vanilla variety.

Black Dog, found in North Damen Ave, has some unusual and downright weird flavors to tickle your taste buds so it’s worth a try.

Some notable gelato flavors include goat cheese cashew caramel and vanilla sea salt caramel, but their ice cream flavors change all the time.

You can find everything from lemon champagne sorbet to Earl Grey and fruit loop flavors, depending on the time of year.

If you’re not into unusual ice cream and prefer to stick to the tried-and-tested flavors, don’t despair – at Black Dog, you can also find some classic yet delicious flavors such as pistachio and chocolate.

Interested in trying them out?

A gelato cone costs approximately $3.50, while a cup costs $4.25.

Visit The Japanese Garden

Japanese Garden In Chicago

If you’re in the mood for some peace and quiet in a dreamy setting, visit the Japanese Garden, otherwise known Garden of the Phoenix.

Located behind Hyde Park’s Museum of Science and Industry, you’ll find this amazing gem of the city filled with quiet pools and breathtaking views.

It will really make you feel like you’re on holiday in Asia.

Take a walk across raised footbridges and enjoy the beautiful streams.

Make sure you go during the spring so that you can witness the beautiful cherry trees in full bloom.

Natural beauty aside, there’s also lots of history behind this garden: it’s a symbol of friendship and respect between the U.S. and Japan that was established over 120 years ago, as Chicago Park District reports.

There’s no admission fee if you want to visit the Japanese garden. Enjoy, and remember to take pictures to show your loved ones.

Related Questions

Is Chicago expensive for tourists?

It really doesn’t have to be, as can be seen by the prices featured in this list of activities to do in the city.

In fact, there are many activities that are completely free, and lots of walking trails and natural sights to enjoy that don’t cost a penny.

Why is Chicago’s motto “urbs in horto?”

This means “city in a garden.”  These words have been used as the city’s motto since the 1830s and basically refer to Chicago’s historic and spectacular park system.

The city has 600 parks and the Chicago Park District is the biggest municipal park manager in the whole country.

Did skyscrapers really originate in Chicago?

Yes, the world’s very first skyscraper was the Home Insurance Company building.

It was built in 1885 and was designed by Major William Le Baron Jenney, as Choose Chicago reports.

The city currently has 119 skyscrapers as well as 1,315 tall buildings, as World Atlas states.


There are lots of interesting things to see in Chicago, even if you only have two or three days at your disposal.

Whether you want to see the sights from the river or go underground and explore a world beneath your feet, there’s something for everyone, and most of the activities and destinations in the city have a colorful history behind them that you’ll enjoy learning about in the process.

Memorable and interesting, Chicago is definitely a city that never leaves you wanting more with lots of activities for everyone to enjoy.

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