20 Unique Things to Do in Downtown Chicago

by Paul Joseph  |  Updated August 1, 2022

Downtown Chicago has a distinctive vibe that sets it apart from anywhere else in the city – and is home to enticing attractions of every kind.  

Visitors admire a painting at The Art Institute of Chicago (Photo: Phil Roeder via Flickr / CC BY 2.0)

Also known as The Loop, the district is at its most vibrant during the week when it hums with professionals going about their working days. But whereas weekends were once deathly quiet, in recent times the district has come alive out of office hours too. It provides the stage for some of Chicago’s finest outdoor cultural events, while several new residential towers now house the city’s large student population who bring a youthful energy to the area. We’ve picked out 20 things you can do downtown that you won’t find anywhere else.

Explore a world class museum

Widely regarded as one of the world’s s great art museums, the Art Institute of Chicago houses a permanent collection that spans every medium from all cultures and historical periods. Housing more than 260,000 artworks and artefacts, the museum has particularly strong holdings in Impressionist and Post-Impressionist painting, early 20th-century European painting and sculpture, contemporary art, Japanese prints, and photography. The venue also hosts regular special exhibitions, as well as daily lectures and gallery tours.

111 South Michigan / Thurs-Mon 11am-5pm Closed Tues-Weds

Another distinguished cultural venue, the Museum of Contemporary Photography is the only museum in the Midwest with an exclusive commitment to photography. Founded in 1976, the museum collaborates with artists, photographers, communities, and institutions both locally and worldwide to present projects and exhibitions that embrace a wide range of contemporary aesthetics and technologies, all designed to promote a greater understanding and appreciation of the artistic, cultural and political implication of the role images play in our world today.

Columbia College Chicago, 600 South Michigan Avenue / Mon-Sat 10am-5pm Sun 12pm-5pm

Discover Chicago’s finest interior architecture

Downtown Chicago is packed full of buildings that are beautiful both inside and out. Visitors keen to see beyond their façades can do so by joining a Downtown Architectural Interiors Tours. For two hours and in the company of an expert guide, you’ll step back into bygone eras to admire the distinctive style of the 1880s through to the elegance of a classic 1920s Art Deco masterpiece, and a vaulted ceiling from the Postmodern era. All  entrance fees are included in the tour price.

Book at GetYourGuide

Inside one of downtown’s architectural wonders (Photo: Inside Chicago Walking Tours / Courtesy GetYourGuide)

Attend a fun-packed festival

Founded in 1997, Lollapalooza is one of the largest and most popular music festivals anywhere in America, attracting more than 150,000 revellers every year. Genres including alternative rock, heavy metal, punk rock, hip hop and electronica all feature, with some of the world’s biggest musical names having performed at the event, including Kanye West,The Smashing Pumpkins, Beastie Boys and Radiohead. As well as live music, the festival has also provided a platform for several political groups and visual artists down the years, including a small theatre troupe reciting poetry.

Grant Park / August each year

Said to be the largest free blues festival in the world, the Chicago Blues Festival sees more than half-a-million music lovers gather in Millennium Park for three days of live stage performances each year. A Chicago staple for almost four decades, the festival features some of the genre’s most revered musical names, along with up-and-coming and local talent. Notable figures to have appeared over the years include B.B. King, Buddy Guy  and Etta James. There are also plenty of local food and drink vendors.

Millennium Park / June each year

A performance at Chicago Blues Festival (Photo: Jennifer Morrow via Flickr / CC BY 2.0)

Visit a fascinating cultural centre

One of downtown’s most popular attractions, the Chicago Cultural Center is at the heart of the district’s cultural life. Spread across an entire city block, the centre is housed within an eye-catching building that is also home to the world’s largest Tiffany stained glass dome. Visitors can spend hours marvelling at its architectural splendour, but inside is where the real magic happens. Whether it’s free art exhibits showcasing local and national artists, music concerts, film screenings, lectures, theatre or dance, there’s always something fun and fascinating going on – often free of charge.

78 East Washington Street / Mon-Sun 10am-5pm

Catch some live comedy

Chicago has an internationally renowned comedy scene, with many of the city’s best comedy clubs located downtown. Whether it’s stand-up, sketch, or improv by established comedians or the latest crop of comedic talents, you’re certain to find the gags that tickle your funny bone. Laugh Factory, Zanies Comedy Night Club and the Comedy Bar are among the downtown venues that put on live acts pretty much every night of the week, and each year the city also stages its own acclaimed comedy festival.

Admire Chicago from up high

One of Chicago’s most iconic attractions, the Willis Tower Skydeck is located on the 103rd floor of what for a long period of time was the world’s tallest building (when it was better known as Sears Tower). Intrepid types can take a lift to the Skydeck, where they can enjoy breath-taking views spanning 50 miles and four states on a clear day. If you dare, step out on The Ledge, an enclosed glass floor balcony that juts out by over a metre from the side of the skyscraper.

233 South Wacker Drive / Mon-Fri & Sun 9am-10pm Sat 8.30am-10pm

Fearless visitors at the Willis Tower Skydeck (Photo: vagueonthehow via Flickr / CC BY 2.0)

Take a wander through Chicago’s “front yard”

The perfect antidote to the urban hustle and bustle, Grant Park spans some 319 acres along Lake Michigan and is home to famous attractions including the Shedd Aquarium, the Adler Planetarium, the Field Museum and the Art Institute. But above all, it is a green oasis in the heart of downtown, and a wonderful place to kick back, relax and enjoy the scenery. Among its centrepiece landmarks is Buckingham Fountain, modelled after one of the extravagant fountains at the Palace of Versailles in France.

337 East Randolph Street / Mon-Sun 6am-11pm

Watch a theatre show

A legendary venue in the heart of downtown, The Chicago Theatre has played an instrumental role in the long and illustrious history of theatre in Chicago, having been the first large, lavish movie palace in America and a prototype for many of the others that followed. Originally built in 1921 today it stages a busy programme of distinguished productions. The building itself is no less impressive, and in 1979 was added to the National Register of Historic Places, in part thanks to its huge trumphal arch motif on its façade which is often compared to the l’Arch de Triomphe in Paris.

Outside one of Chicago’s famous theatre venues (Photo: jphilipg via Flickr / CC BY 2.0)

Indulge in some retail therapy

For shopping in downtown, there’s only one place to head and that’s the Loop Retail Historic District. Located along Slate Street, the area has long been known for its assortment of department stores and independent shops, selling everything from high-end clothing to jewellery to everyday essentials. Among the most eye-catching shopping outlet here is the neo-gothic North American Building, clad in cream-coloured terra cotta and housing various retail stores on the first floor.

Join a guided walking Tour

There’s no better way to get to know a city than by walking around it, and as one of the most walkable cities in America, Chicago is the perfect place to hit the streets. If this takes your fancy, then Inside Chicago Walking Tours hosts a range of guided tours around downtown tours. Tours typically last two hours and cover around a mile and a half at a leisurely pace, during which time you’ll gain a deep insight into Chicago’s architectural heritage, all brought to life by your guide’s fascinating stories.

A dramatic view of one of the ‘secrets of the Loop’ (Photo: Inside Chicago Walking Tours)

Pick up some great produce at a French market

Chicago is a mecca for food-lovers and one of the best places to head for sampling some of the city’s varied cuisine is the Chicago French Market. Home to over 30 speciality vendors, the bustling market features a huge variety of stalls selling French ingredients to take away as well as several dine-in venues and grab-and-go options too. Open all day, the choice here will blow your mind, with everything from meatball subs to lobster rolls, ceviche to empanadas, Belgian fries to mac n cheese, chocolate truffles to French macarons, and plenty more. There are also regular Happy Hour specials, live music, and other events.

131 North Clinton Street / Mon-Fri 7am-7.30pm Sat 8.30am-5.30pm Closed Sun

A mouth-watering assortment of delicacies at the Chicago French Market (Photo: Chicago French Market)

Enjoy some public street art

Chicago’s vibrant art scene extends beyond its museums and exhibition spaces and into its public spaces. Among the most notable displays of public art in downtown are at Daley Plaza, where Picasso’s 50-foot-tall untitled sculpture takes centre stage and has become an enduring symbol of Chicago itself. Another can be found at Chase Tower Plaza, a minute’s walk south, where Chagall’s monumental The Four Seasons mosaicmural turns heads with its composition of thousands of inlaid fragments in over 250 colours, representing the arrival of spring, summer, winter, and fall.

Hop on a bike tour

Another great way to experience Chicago is on a bike tour. One of the most popular companies for traversing Chicago’s flat terrain, vast network of sidewalks and trails, and expanses of green spaces by bike, is Bobby’s Bike Hike, who run a range of cycling tours (among others), delivering a unique insider’s view of the culture, history, architecture, and little known facts that define the iconic Windy City. Tours are themed around particular areas of interest, such as food or gangsters, and there are also kid-friendly tours, which take in more family-oriented sites along the way, such as a petting zoo.

Book at GetYourGuide

Tour guests pose for a snap mid-cycle (Photo: Bobby’s Bike Hike-Chicago Tours & Rental / Courtesy GetYourGuide)

Enter a murky world of spies

Dedicated entirely to the mysterious world of espionage. Safehouse Chicago is a themed nightclub and restaurant awash with authentic spy-related artefacts, pop culture references and spy paraphernalia, including original props from James Bond movies. From the minute you locate its top-secret entrance – marked only by a small plaque next to a nondescript red door with a sign that reads “International Exports” – and pass the clearance test to prove you’re not a double agent, you’ll find yourself immersed in a murky world. There’s even a secret exit, because, after all, a good spy never leaves the same way they came in.

60 East Ontario Street / Sun-Wed 11am-12am Thurs-Fri 11am-2am Sat 11am-3am

Check out downtown from a chopper

A helicopter ride is a unique experience, owing to their ability to fly lower than other forms of air transport. Run by experienced, professional pilots, the Downtown Helicopter Tour lets you see  the vibrant district from a truly memorable vantage point. After meeting at the Chicago Vertiport, you’ll be given a brief safety tutorial before taking to the skies for 15 to 18 minutes that you’re guaranteed to cherish forever. Complimentary soda/pop and bottled water are all provided.

Book at Viator

A helicopter soars through the air above downtown (Photo: Breeze Helicopters / Courtesy Viator)

Get a flavour of Chicago’s diverse food scene

Outside of Italy, Chicago is one of the best places to find authentic pizza. The Downtown Chicago Walking Pizza Tour invites lovers of the doughy delicacy to explore the city’s rich pizza landscape. Over the course of one hour, you’ll traverse downtown by foot, stopping off at different pizzerias in River North, the Loop and along Magnificent Mile to taste a variety of different pizza styles while your guide provides in-depth commentary and answers any questions on pizza-making techniques, the difference between Italian and American pizzas, and the history of Chicago’s pizza scene.

Book at Viator

For an even more wide-ranging foodie experience, Taste of Chicago is an annual lakefront extravaganza which sees many of the city’s best restaurants serving up delectable fare via pop-ups and food trucks. From classic Chicago specialities to international cuisine to chef-inspired creations, every palette and preference is catered for here, while budding chefs can pick up tips at live cooking demos. Other highlights include a silent disco, nightly concerts, and a specially constructed kids’ playground complete with a Ferris wheel and inflatables.

Grant Park / June each year

Marvel at exotic marine life 

Perched on the banks of Lake Michigan, Shedd Aquarium is home to more than 30,000 marine animals, including sea otters and seahorses, beluga whales and bluegills, reef sharks, stingrays, lake sturgeons, and Pacific white-sided dolphins. An ideal day out for the family on a rainy day, the aquarium is packed full of exhibits that reveal the secrets of our planet’s waters – and what lies beneath. It also has a strong conservation focus, with a number of the animals that reside here having been rescued from around the globe.

1200 South DuSable Lake Shore Drive / Mon-Sun 9am-6pm

A member of staff interacting with a dolphin in the water at Shedd Aquarium (Photo: LABabble via Flickr / CC BY-ND 2.0)