Weather permitting, I would always recommend starting off with a self-guided walking tour. Chicago’s grid system makes it very easy to navigate, and all my recommended hotels are an easy walk to most of the major outdoor artworks. If you fancy yourself a bit of a photographer, or you just love posting on your favorite social media accounts, this tour is made for you. Consider what you might wear in relation to the works - mainly dark tones and neutrals, but don’t forget the Calder red or mosaic rainbow to come! These works can be viewed publicly most times of the day and night, or both if you like. You can rush through it in a couple hours, or take your time throughout, taking breaks for coffee, meals, or drinks. There is no one right way to explore!

Self-Guided Walking Tour

I have organized this in an order that should be ideal to walk from start to finish, but it is by no means the only way to go. Never hesitate to build your own adventure!

• Flamingo by Alexander Calder, 1974 (210 S Dearborn St): Found in an open plaza, this is a great space to play. If you have studied art, you might be thinking about contrast, negative space, or simply the scale of the work. Consider how the materials complement the architecture around it.

• The Four Seasons by Marc Chagall, 1974 (10 S Dearborn St): Each of its 128 panels offers a special set of details and a rainbow of colors. Depending on the time of year and day, the vibrancy of those colors can look vastly different. You can walk around it, feeling the seasons change, or sit nearby and just take it in. While this work is more protected than most (it has not always weathered well), you can still walk right up to it and take in the minute details. Take your time with this one.

• Chicago (The Sun, the Moon, and One Star) by Joan Miró, 1981(77 W Washington St): Meant to represent a celestial female figure, grounded in earth and reaching for the stars, this work is often overlooked in the celebrated outdoor sculptures of Chicago. It has had a mixed reception over the years. What is your immediate reaction? Does it change as you spend more time with it? Love it or hate it, “Miss Chicago,” as she is often affectionately called, is here to stay.

• Untitled / “The Picasso” by Pablo Picasso, 1967 (50 W Washington St): Picasso’s gift to the city, this unidentified figure has been identified in many ways by many people, and it is still simply known as “The Picasso.” Originally met with much controversy, it is now a beloved symbol of Chicago.

• Monument with Standing Beast by Jean Dubuffet, 1984 (100 W Randolph St): Supposedly composed of four parts depicting a standing animal, a tree, a portal, and an architectural form, this abstract, graffiti-like sculpture has always drawn attention. Another you are encouraged to walk around and through and touch as you please, Dubuffet hoped this work would resonate with the average person on the street.

• Take note as you cross the river of the Merchandise Mart, as after dark you will be able to see the latest “Art on theMART” light installation. Launched in 2018, Art on theMART is the world’s largest permanent digital art projection. This is also a living project, with new works submitted annually and rotated regularly throughout the year. If you like visiting trade shows, definitely check their events page to see if the Merchandise is currently hosting one of their many!

• Crossing by Hubertus von der Goltz, 1998 (334 N La Salle Dr ): After you cross the river, check out this cheeky piece, meant to symbolize the convergence of commercial and cultural elements along the LaSalle Street Corridor. Definitely worth a walk around - does it feel balanced or precarious to you?

• Bronze Cow by Nathan Mason, 1999 (88 E Washington St): The last cow standing from America’s First Cow Parade, and a symbol for Chicago right outside the Chicago Cultural Center. Definitely worth a visit, and also offering free admission, they have written up a helpful section for “what to see in an hour.”

• Cloud Gate / “The Bean” by Anish Kapoor, 2006 (201 E Randolph St): A favorite since its unveiling, “The Bean” hardly needs any introduction. It is also a touch-friendly work, inviting unique reflections of the cityscape from every angle. Take your time walking around, under, between, and make sure to visit it in different lights and seasons. Furthermore, the Cloud Gate invites you into Millennium Park, another must-visit for anyone coming to Chicago. Over the past several years now, the city has expanded the park to include more walks, activities, and entertainment options for all. Not everything is free, but the walk certainly is, and it is a beautiful way to explore the city when you are ready to step away from the skyscrapers and see the lake again.

• Crown Fountain by Juame Plensa, 2004 (201 E Randolph St): The most seasonally varied of the artworks listed here, Crown Fountain is definitely most fun to visit in the warmer months, when the fountain itself is running and ready to play. It’s dynamic, it’s fun, dogs and children are welcome in its space. Replacing the old-school gargoyle fountains of gothic times, the artist gathered images of Chicago locals to feature instead.

• Muddy Waters Mural by Eduardo Kobra, 2016 (17 N State St): And if you still have one last stop in you, a more modern mural to cap off the tour! A nine-story tribute to the artist, it celebrates his legacy in a city known for its love of the blues. If you love this, definitely consider another walk via the Loop Mural Walk site!

This concludes the absolute musts within easy walking distance in downtown Chicago, but it really is only the beginning. For those willing to venture a little further (still a manageable walk), definitely check out the Wabash Arts Corridor around 635 S Wabash Ave - a living urban canvas in the South Loop. Or walk over to Magdalena Abakanowicz’s “Agora” (1135 S Michigan Ave) for a more recent addition to the outdoor sculpture series. The possibilities really are endless for great art in this city!

Cocktails & Snacks

• The Riverwalk (E Wacker Dr - for one of many entrances): It may not be the best ever cocktail or snack you have had, but the riverwalk is gorgeous and thriving in the nicer weather months. Honestly, the walk itself in winter is lovely too, but in the outdoor seasons, I still recommend grabbing a drink and hanging on the steps here.

• Cindy’s & The Drawing Room (inside the Chicago Athletic Association, Floors 4 & 2 respectively, 12 S Michigan Ave): Even if you decide not to stay at this particular hotel, its proximity to Millennium Park and views across make these stops ideal along your art tour. The best views of the park itself come from the Drawing Room, connected to the lobby of the hotel, and good in any season for a cozy stop for a drink. Cindy’s on the upper floor offers ideal lake views.

• Three Dots and a Dash (435 N Clark St): A classic tiki venue, and ideal if you love a good tropical cocktail like I do. It celebrates the old-school tiki world with a proper escape from the outside world. Should be ideal after a day of walking.

Pubs, Beer, Pizza, Dives

• Monk’s Pub (205 W Lake St): Great stop for a Chicago Pub vibe during your walk! A favorite since 1978, it has a substantial draft beer selection, while also offering a full kitchen and options for everyone.

• Stocks & Blondes (40 N Wells St): This is definitely for your dive bar lovers, but also for a spot in the Loop, it is a solid, affordable lunch or late night meal too. They always have a good selection of locally brewed beers too.

• Lou Malnati’s (439 N Wells St +): One of the most famous and solid chains for deep dish pizza. One of their locations will never let you down.

• Exchequer Restaurant & Pub (226 S Wabash Ave, Chicago, IL 60604: Less famous and popular than Lou Malnati’s, but if you want something close in your tour that has an old school Chicago feeling, this stop will do it for you.

Restaurants +

• Gene & Gorgetti (500 N Franklin St): A Chicago classic steakhouse since 1941. Don’t be afraid to try their traditional “garbage salad.”

• Girl & The Goat (809 W Randolph St): For all the most exciting restaurant and bar options right now, the West Loop is really where to go. This spot is considered a staple for the area now, and it’s one of four within the area by Top Chef’s Stephanie Izard. You can’t go wrong with any of them.

• Russian Tea Time (77 E Adams St): It might sound a little crazy, but if you want your art walk to feel especially fancy, I recommend checking out the afternoon tea service here as part of your day. It is a nice restaurant, but the dress code isn’t too serious, and during the day in particular they are more flexible. I personally have not tried their dinner, but I imagine it holds up to the delicious and special tea service.