10 Essential Chicago Bucket List Experiences For 2021

A year-round list of must-do activities in Chicago for both local and tourist alike.

Elliot McGowan Elliot McGowan

10 Essential Chicago Bucket List Experiences For 2021

“Going to Chicago was like going out of the world.” —Muddy Waters

2020 will go down in history as a year plagued with negative superlatives, unprecedented events, and months of turmoil. At the same time, it was undoubtedly an eye-opening year for millions. It taught us about ourselves, what we cherish most, and the people and places we turn to in times of hardship. Most of all, it reminded us that we should never take our health and our freedom for granted.

Without dealing in clichés and overused proverbials like ‘life is short’ and ‘carpe diem’, the last year reminded us to make the most of every minute going forward. We spent enough time with our great city brought to its knees to realize that now we should enjoy it to its absolute maximum with the time afforded to us.

This is a bucket list of what to do in and around Chicago – a things-to-do-before-you-die type of list aimed at Chicagoans and tourists in equal measure. Whether you’re a seasoned local or a thrill-seeking visitor, these are the best ways to experience Chicago and the must-do activities around the city.

1. Check Off Chicago’s Iconic Landmarks

Image from Shutterstock

If there is one thing Chicago is home to it is an abundance of extraordinary landmarks. For that reason, we’re kicking off with the most predictable recommendation. Any city-specific bucket list can’t go without mentioning its picturesque postcard attractions and Chicago is one of the most photographed places in the modern world for good reason.

Before you do anything in Chicago make sure to take in its most famed features. Sit mesmerized by The Bean, dance under the spurt of Crown Fountain, walk along Navy Pier, and enjoy the smaller iconic landmarks like The Historic Water Tower, Calder’s Flamingo, and the Picasso Statue. The list of renowned museums, skyscrapers, and parks goes on and on but it is these iconic landmarks that create Chicago’s prestigious character.

2. Peruse Chicago’s Legendary Street Art

Image from Pexels / Chait Goli

The consequence of a thriving artistic community is not just a plethora of museums and stunning art installations. The street art and graffiti scene in Chicago is alive and kicking more than ever before with new pieces popping up all over the city every week. Some of these are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now as much part of the Windy City’s identity as its iconic sculptures and landmarks.

Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for equality, celebrate different heritages, and honor the heroes of society. Chicago’s art scene is another essential experience and with the many talented local artists frequently at work, it is equally as exciting for both tourists and locals alike.

If you’re not familiar with Chicago’s art scene and would like to learn about its history and the inspiration behind some of its famous murals you can head to our Must-See Chicago Murals article or jump on a West Town Street Art Walking Tour of Chicago’s famed mile-long street art corridor known as the B_Line.

You can grab tickets for an art walking tour here.

3. Revel In The Rooftops Of River North

Image from Shutterstock

From the streets to the rooftops, equally as famed as its artistic community is the Windy City’s sublime skyline. Among its soaring cityscape, numerous rooftops can be found offering exhilarating experiences drinking and dining among the skyscrapers of Chicago. You will struggle to find a more memorable Chicago evening than one spent sipping cocktails under the stars.

Of the many choices, there is always something happening at River North’s vibrant and verdant Joy District rooftop, whilst London House Chicago is a photographers paradise for its stunning vistas of the Chicago River and Michigan Avenue. For a really iconic Chicago photo, however, Cindy’s Rooftop in the Loop offers sweeping panoramic views of Millennium Park and award-winning cocktails from a lavish setup.

One of our picks for this summer combining art and rooftops has to be Chicago’s new interactive urban art rooftop parties. Guests can learn the ins and outs of mural-making from a local spray paint artist whilst soaking up those rooftop vibes accompanied by a live DJ.

You can grab tickets to an interactive rooftop urban art party here.

4. Brave The Willis Tower Skydeck

Image from Unsplash

Talking of skyscrapers, no trip to Chicago is complete without heading up Sears Tower, more formally known as the Willis Tower. Seeing one of the world’s most famous skylines from the tallest tower in Chicago (and the third tallest in the United States) is an absolute must. Take a 60-second ride up to the cloud-piercing height of the Skydeck and enjoy unparalleled 360-degree views over Chicago. 

Millennium Park, Navy Pier, and many of Chicago’s most famous landmarks are all visible from the top making it truly one of the most unique experiences Chicago has to offer. The glass ledge on the 103rd floor allows you to breach the building’s dimensions and stand 4ft outside of its walls. Looking down you’ll see a 1,353 ft drop staring back up at you as you sit in a tiny glass box protruding outside of what was once the world’s tallest building. Equally as impressive in the day as it is at night, it’s not to be missed.

You can head to the Skydeck website for more information and tickets.

5. Kayak Down Chicago River

Image from Shutterstock

Back down at a non-nauseating height, there’s a unique way of seeing Chicago from a whole different perspective. Kayaks and paddleboards can be rented from various operators at both Monroe Harbor and Chicago Riverwalk locations but it is the river where the most unique experience can be found.

Flanked either side by Chicago’s famous highrise architecture, you can venture through the city’s heart via skyscraper canyons and under historic bridges. An evening kayak makes for a truly memorable night navigating the waters while the sun sets and the hustle and bustle of the riverwalk activity takes off around you. Single kayaks, tandem kayaks, and kayaking tours are all available, allowing you to navigate Chicago’s winding river at whichever pace you desire. Learn about the sights with a tour guide or explore the river independently and see where it takes you.

You can head to Urban Kayaks for more information.

6. Bike Along Lake Michigan

Image from Shutterstock

While kayaking offers a fantastic way to see the city via the river, cycling offers a wonderful way to explore the lakefront and again combines exploration with exercise. Cycling has flourished in popularity in recent years and Chicago is consequently becoming more and more bike-friendly.

However much the city changes, The Lakefront Trail will always be an iconic Chicago bucket list experience. Running for 18 miles from the south of Chicago up to the north you’ll pass harbors, museums, and beautiful beaches, with the cities sensational skyline on one side and the blue waters of the lake on the other.

Look out for Bike the Drive at the end of May each year when thousands flood the 30-mile stretch of Lake Shore Drive. For all other times of the year Bikes can be easily rented for full days and Chicago’s bike-share program offers over 6,000 Divvy bikes. For newcomers, the Chicago bike tour, known as Bikes, Bites, and Brews takes guests on a bike tour tasting signature Chicago dishes and sampling legendary Chicago craft beer along the way.

You can grab tickets to a Chicago bike tour here.

7. Jump Into 2021 With Chicago Skydiving

Image from Shutterstock

This is a little bit of a jump from cycling along the lakefront but those quintessential international bucket lists usually have a few spots reserved for the typical do-before-you-die activities such as swimming with dolphins, bungee jumping, and, of course, skydiving. The latter is by far the most accessible in Chicago.

Now, we’re not saying jump out of a plane in the freezing skies above Chicago straight away, but we are saying give it a go in one of Chicago’s indoor centers to get a taste of what it is like and why it is such a popular bucket list experience. With a state-of-the-art iFly Indoor Skydiving Center in Lincoln Park and another iFly Indoor Skydiving Center in Rosemont, Chicago is home to two conveniently located cutting-edge centers where kids and adults can get the same sensation you’d get 12,000 feet up in the sky.

If the experience has you wanting more you can test your vertigo above Chicago’s iconic skyline at one of the world’s largest skydiving resorts named Skydive Chicago and boast that you’ve jumped out of a plane above the Windy City.

You can grab tickets to an indoor skydiving center in central Chicago here.

8. Bathe In AIRE’s Ancient Baths

Image from Beaire.com

If the thought of free-falling towards the Earth’s surface might have had some of your hearts racing so we’re going to bring you back down to earth with this next must-do. There is simply no better place in Chicago for some rest and relaxation than AIRE’s Ancient Baths.

Located in a restored historic River West factory dating back to 1902, the baths are inspired by the traditional Roman, Greek, and Ottoman ancient experience of bathing. This preserved structure has been restored to its original splendor and you can now find optimum relaxation within the exposed brick, wooden beams, and industrial columns of the building.

The unique body and mind experience offers baths of different temperatures, relaxing massages, couples experiences, and more. With all the activity and experiences taking place in the Windy City sometimes we just need to cool off for a bit and there is no better place than Chicago’s ancient baths.

You can head to the AIRE Ancient Baths website for more information.

9. Experience A Gorgeous Candlelight Concert

Artifact Events’ historic courtyard.

Another relaxing yet inspiring experience can be found in venues all over Chicago. Few activities are as enchanting as watching one of the wildly popular Candlelight concerts. The candlelit spectacle is another unique Chicago bucket list experience whether it is an indoor or outdoor show. Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres in some of Chicago’s most unique locations.

Places like Artifact Events’ historic courtyard and Ace Hotel’s prairie garden offer an evening experiencing Chicago’s musical talent in some of Chicago’s off-the-beaten-path hideouts. There are concerts happening throughout the year offering both Jazz & Soul concerts and traditional classical music concerts.

Here are a few recommendations:

You can find moore information and tickets for Candlelight concerts here.

10. Skate Or Climb In Maggie Daley Park

Chicago's Maggie Daley Ice Rink
Image from Shutterstock

Along with its art, gastronomy, and skyline, Chicago’s plethora of parks are another source of pride and pleasure. The Loop’s Millenium Park and the connecting Maggie Daley Park are particularly beloved hotspots, in the latter, you’ll find another paramount bucket list experience.

Surrounding an incredible climbing wall in Maggie Daley Park winds a public skating ribbon. In the summer it is used as a scooter and rollerblade path whilst in the winter you can experience “alpine in the city” when it becomes an iconic public ice rink and one of Chicago’s most beloved winter-time activities.

The quarter-mile winding ribbon curves up and down around the 40-foot climbing wall twisting, turning, inclining, and declining with the city’s stunning skyline in the backdrop. It’s a truly unforgettable experience, whatever the season. For those keen to challenge themselves a little more, during the warmer seasons, you can have a shot at scaling the climbing wall. There are varying routes of many different difficulties so you need not worry about not being able to make it to the top.

You can head to the Maggie Daley Park website for more information.

[Featured Image from Beaire.com]

See more: 25 Must-See Street Art Murals That Prove Chicago’s Art Scene Is Legendary

Secret Guides Sponsored Things To Do