19 Best Things to Do in Chicago

by iROOMit Team
26 May 2022
11 min read

Garfield Park Conservatory

Step into the humid, glass-enclosed domes of Garfield Park where the air is clean thanks to thousands of jewel-toned plant specimens filtering toxins throughout. The space is fashionably untamed across its verdant showcase of flora from wet and dry environments, and those between. Spread across twelve acres, there's abundance year-round, from the colourful spring flower show to permanent indoor exhibits and holiday displays. Plant and garden enthusiasts should make the conservatory—easily accessed by Green Line—one of their stops

Chicago Pizza Tours - Original Chicago Pizza Tour

Chicago Pizza Tours are a fun and informative way to explore the city's most famous culinary export. The tours adapted in 2020 to include a bit of a luxury upgrade. The Quarantine Pizza Tour features everything you love and expect from a food-focused adventure—with the addition of a limousine escort from where you're staying and YouTube videos guiding you along the way as the pizzerias deliver the pies to your door. They can fit groups as small as nine and large as 22.


Urban Kayaks

Kayaking on the Chicago River or lake front is one way to shake up your perspective while visiting. Urban Kayaks offers tours along either. Move through the pulsing heart of the city on the river or travel Lake Michigan and circle Museum Campus (featuring the Field Museum, Adler Planetarium, Shedd Aquarium and Soldier Field). A night tour on the river boasts views of the glowing Merchandise Mart, which is showered in rotating, digital art displays projected onto the building. A one and a half hour skyline paddle in Lake Michigan gives you all the tourist sites without the foot traffic and crowds, showing you Grant Park and Navy Pier on a route few tourists trek.


FEW Spirits

Among the first whiskey distilleries to open in Chicago post-Prohibition, FEW offers an intimate view of the entire whiskey-making process. Walk through the stillhouse, learn the history of the brand from the founder, and, of course, taste the goods! The tour is ten dollars, includes a tasting, and the distillery is easily accessed by public transit. Tours are available on Wednesdays and Saturdays only. As long as that fits with your schedule (and you're over 21, of course), this is a fun and flavorful way to spend an afternoon.

The Morton Arboretum

Located about 30 minutes west of downtown Chicago, the Morton Arboretum feels like a world away. It's a pastoral escape that feeds the mind and heart. Art installations on site are rotated seasonally, several of them are dedicated to the natural sciences, such as the living exhibit dedicated to tree growth. 'Human+Nature' is the current installation here, showcasing the work of acclaimed sculptor Daniel Popper. Five pieces are currently on display in various locations across the arboretum's 1,700 acres, making this Popper's largest exhibition to date anywhere in the world. Open from 7:00 a.m. to sunset, daily—it's a relative bargain at $16 a ticket. With a maze garden and over 16 miles of hiking trail, this is the ideal urban getaway for outdoorsy sorts looking to decompress.


Art on theMART

Smack dab in the center of Chicago's coveted River North neighborhood is the world's largest permanent digital art projection. Onlookers gather nightly to observe a unique display of visual effects taking shape upon the 2.5-acre riverfront facade of theMART building. This free, self-guided public art experience is certainly a spectacle amidst the already impressive Chicago cityscape. If you're compelled by what you see, the art on theMART website offers more information on the artists involved.


Executive chef and owner Noah Sandoval has a flair for elegant-yet-stripped down design. It's evident in the composition of his cuisine, but also immediately felt from the moment you walk in the door at Oriole. Traversing a nondescript West Loop alley, you emerge into a dining den defined by exposed brick and wooden beams. It exudes an almost Scandinavian sort of vibe—or hygge, if you like. The two Michelin stars hanging from the wall are well-earned. A parade of small bites on the tasting menu skew towards seafood—smoked roe gracefully adorns sablefish belly; raw oysters are swathed in pork consomme; seared loup de mer is a perennial standout. All of it is rendered as high-art on the plate. But it's more than just a feast for your eyes. At $285 a person—exclusive of tax, tip, and wine—this is definitely a special occasion splurge.

Ping Tom Memorial Park

More hidden than others, but not secluded—it’s just blocks away from Chinatown Square—Ping Tom Park has a special serenity to it. With its pagoda-style pavilion and bamboo gardens, the park is inviting to relaxing strolls, leisurely biking and roller-skating, and small gatherings along the river. Afterward, you’re close to some of the best dim sum and boba tea Chicago has to offer.


Museum of Contemporary Art, Chicago

The MCA is one of the city’s museums that’s in a near constant state of transition. With its relatively small permanent collection, it relies on special shows—from large scale installations to video, fashion, music, photography, and more—that showcase just as many rising local talents and underground, avant-garde renegades as recognizable names. Past exhibits include David Bowie Is, Takashi Murakami: The Octopus Eats Its Own Leg, and Virgil Abloh: Figures of Speech. The museum is also known for its hosted talks between writers and artists, and various performance series. It also has one of the best gift shops...ever.

Lincoln Park Zoo

Located in the heart of Chicago's Lincoln Park, this zoo offers free, family-friendly entertainment year-round including the festive Zoolights around the holidays (reservations are required for all visits though). The sprawling grounds are seamlessly woven into the park’s landscape, balancing open, natural spaces and numerous animal exhibits. If you skip the pricey concessions (but maybe spring for a paddle boat ride), Lincoln Park Zoo is a great option to keep all ages occupied while staying on a budget.

Bloomingdale Trail

Chicago's answer to New York's High Line, the Bloomingdale Trail—a.k.a. The 606—is a nearly three-mile, elevated greenway running west and east on the city’s North Side. Unlike its NYC counterpart, the trails are wide enough to accommodate active patrons running, walking and cycling without running off more casual strollers, the formerly abandoned rail line is also lined with public art installations and gardens. During fairer weather, the trail also hosts various free events for families with young children.

Humboldt Park

One of Chicago's prettiest parks, this 207-acre green space is located within the larger neighborhood of Humboldt Park (both are named for German naturalist Alexander von Humboldt). It's home to several statues—including one of its namesake, and two bison that were placed there during the 1893 World's Fair—as well as the National Museum of Puerto Rican Arts & Culture, located in the park's former stables. It's easy to drop in if you're headed down the 606 trail, but the park is big enough that it could take more than half a day to do all of it, so it's best if you're not in a rush.

Gangsters and Ghosts

There is definitely a laidback homespun sort of vibe to this two-hour tour. You're going to cover a lot of ground here—1.5 miles in total, with a 20 minute break at the famed hang of an early 19th Century gangster. This is something that appeals to history buffs, but ones that pack sneakers when they travel. Not recommended for anyone who's a bit squeamish at true tales of blood and gore, but for folks that yearn to learn more about the mobster days, don't sleep on this one.

Chicago Lakefront Trail

The 18-mile long trail hugs the coast of Lake Michigan, offering almost all manner of activity along the shore. From sandy beaches and sprawling parks, to some of the best views of the Chicago skyline, the Lakefront Path is one of the city's great public treasures, enjoyed by visitors and locals alike. Runners and cyclists love the width and ease of use of the trail, while intramural type teams make use of the many open spaces found up and down the path. If you don't want to run around, there’s plenty of room to just sit and people watch, as well as check out a number of art installations that pop up throughout the year.

Green Mill

Do not come here expecting fancy drinks—or anything fancy, really. This is living, breathing history. And it's a rocking good time. The Green Mill is a warm and inviting throwback to a bygone era. There’s live jazz, cheap drinks, and loads of local history (Al Capone used to have a booth reserved here during Prohibition); what's not to love? Bar eats are not on the menu here. Bring your own potato chips if you think you'll need a snack (no one will judge you). The craft beer list has expanded commendably over the past few years. So grab yourself a cold one or a whiskey soda and see where the night takes you.

Chicago Architecture Foundation River Cruise

Run by the Chicago Architecture Foundation, the Architecture River Tour is one of the most polished operations in town (and a wonderful alternative to some of the cheesier tours). Taking place on a barge in spring, summer, and fairer fall weather, the cruise explores Chicago's beginnings from various branches of the Chicago River—offering both day and evening tours. While groups are typically large, the Architecture Foundation-trained docent speaks via loudspeaker, audible from throughout the boat. (Pro-tip: Head straight upstairs when you board and snag a seat in the rear for optimal views.) In 90 minutes, you'll get to know 50 buildings along the Chicago River, hear secrets about a map of the river's topography hidden in plain sight, and learn about the only skyscraper in the skyline designed by an award-winning female architect.

Promontory Point

This man-made peninsula in Burnham Park has become a favourite gathering and photo shoot spot for locals due to its manicured landscape and rock formations along the lakefront. Our plan of attack here is to have a picnic at the point, then walk among a number of public art works edging the surrounding park. Some of the most interesting sculptures, such as Sounding Bronzeville and La Ronda Parakata, are actually within the Burnham Wildlife Corridor, which is composed of the Burnham Centennial Prairie, Burnham Nature Sanctuary, and McCormick Bird Sanctuary.

Rotor Zen Helicopters: Legacy Helicopter Tour of Downtown Chicago

If money is no object and you've got some time to plan ahead, why not soar high above the skyscrapers in a helicopter for one of a kind views of the city? For small groups of two or three, you'll be surprised at just how much your pilot can show you in just 30 minutes. You'll get to see Chicago's biggest tourist sites, like Navy Pier, Willis Tower (formerly Sears Tower), Soldier Field, and the Lincoln Park Zoo, from a whole new vantage point. A half-hour flight seeing tour of the city starts at $199 per person.


Intuit: The Center for Intuitive and Outsider Art

Among the only museums in the world dedicated wholly to "outsider art," Intuit is an impressive shrine to self-taught creators across all forms of media. Beyond an unassuming, brick facade, you’ll brush up against a concise-yet-vibrant collection of paintings, sculptures and assorted ephemera. The collected work draws you in with an air of unconventional audacity. This is a whimsical environment with an industrial edge. Exhibits are spread out with ample room for wandering and gazing at your leisure. The gallery is curated by passionate docents who are committed to the cause of promoting the artistic output of marginalized creatives.

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