A walking tour isn’t just for tourists. In a city with such robust architectural history (the first skyscraper in the world was built here!), there’s always something new to learn about Chicago’s buildings and the people who built, lived, and worked in them. Whether you’re interested in gawking at terra cotta façades or following in the footsteps of 1920s gangsters, these free (and/or practically free) Chicago walking tours are a surefire way to spice up your daily quarantine walk. Here are our top ten picks.
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1. Chicago Greeters
Ever heard of a Chicago Greeter? No, it’s not a new beer-and-a-shot combo; it’s your new favorite tour guide. Sponsored by Bank of America, the Chicago Greeter program invites enthusiastic (and well-trained) residents to lead two-to-four-hour tours of different Chicago neighborhoods, pointing out landmarks and historical sites along the way. (The only catch: tour bookings are required at least 10 business days in advance.) In the mood for a tour sooner than that? International Greeter Day is Saturday, September 19, which you can celebrate by downloading a self-guided tour of neighborhoods such as Chinatown, Ukrainian Village, Pilsen, and Hyde Park.
Image credit: Friends of the White City/Facebook
Travel back in time to the 1893 World Columbian Exposition with a Friends of the White City tour. While their guided tours are on hold until further notice due to the pandemic, their free app can lead the way instead. Take a stroll through Jackson Park and imagine the grand buildings that were built just for the fair, with help from the app’s videos, photos, and text. Get ready for your brain to melt a little bit as you stand among the trees where the Manufacturers and Liberal Arts building once stood, which was so huge that it could have fit the Willis Tower inside (horizontally). In the mood to see a World’s Fair building IRL? Walk to the north side of the park and take a lap around the Museum of Science and Industry, which was originally the fair’s Palace of Fine Arts.
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MetroWalkz doesn’t skimp on the details in its self-guided walking tours—in addition to all the historical and architectural information you’ll expect, they also tell you fun insider tips, like where to stand to peek inside a walled-off courtyard, or when to turn around to take in a full, fantastic view. Take your pick from nine tours, including an in-depth exploration of Gold Coast, where you can learn about Potter Palmer and the other wealthy historical figures who commissioned some of the city’s grandest homes. Notable architects of those mansions include Burnham and Root, Frank Lloyd Wright, Louis Sullivan, Stanford White, and more. Just visit their site to pull up a free tour on your phone and tap your way from landmark to landmark.
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What would travelers do without Frommers? The savvy travel site outlines 10 self-guided tours in its guide to Chicago, which you can take at your own pace. Choose from an architecture-focused loop around the Loop, a stroll past notable landmarks of Wicker Park and Bucktown (we see you, shoutout to filming locales from The Real World), or perhaps take a trip to Hyde Park (hello, early When Harry Met Sally scenes). Frommer’s has more than just hot tips on Hollywood filming spots, though—it also suggests the best times of day to start your tour, and where to stop for a snack break. (Just do a quick Google ahead of time to make sure any indoor destinations are accessible right now.)
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The GPS My City app is an ideal tour option for people who don’t want to use up all their cell phone data, thanks to its offline functionality after downloading your Chicago tour of choice. In the free version of the app, you can choose from seven sightseeing walks, which include trips to Chinatown and Old Town, as well as a three-hour tour dedicated to Loop architecture. In the mood to forge your own path? You can build a custom walk centered around the sites that interest you, and the app will whip up an efficient walking route and accompanying historical information. Plus, the app has the scoop on 1,000 cities around the world, so whenever traveling becomes a thing again, you’ll want it in your back pocket.
The Best Practically Free Walking Tours (After Membership Fees)
We know, we know, these technically aren’t tours for free. But if you like architecture and history enough to take more than one tour per year, then it might pay off in the long run to buy a membership to one of these bastions of Chicago’s architectural history. After paying your member dues, the perks start rolling in, including “free” tours.
6. Frank Lloyd Wright Trust
Members of the Frank Lloyd Wright Trust can visit the famed Prairie style architect’s home and studio in Oak Park, as well as Hyde Park’s Robie House, for free throughout the year. More in the mood for the Rookery Building or the Emil Bach House? You can score discounted member pricing for those tours, too. Additional member perks include discounts on merch and visits to other Wright sites in the region, and a subscription to the charmingly named Wright Angles magazine.
7. Chicago Architecture Center
The Chicago Architecture Center is more than just its famous river cruise (although that’s extremely fun, too). Its team of 450+ docents leads 65 different walking tours around the city, which members can attend for free. In the mood for Art Deco skyscrapers, Mies Van Der Rohe, or sacred spaces? The CAC has you covered with its array of tours, which reaches beyond the Loop to neighborhoods on the North, West, and South sides, too. Other member benefits include free admission to the Chicago Architecture Center itself (home to an intricate scale model of the city), discounts on river cruises, and more.
Pro tip: The Chicago Architecture Center also organizes Open House Chicago every October, which invites the public to explore compelling Chicago buildings across the city, completely for free. (Members still get some perks, though.) This year’s sites haven’t been announced yet, but you can check out last year’s 350+ locations on this map to get a taste of what 2020’s lineup might bring.
The Best Paid Walking Tours
OK, so these walking tours aren’t free, but they cost less than a bottle of Malört, so they’re practically free, right? Either way, they’re too cool to miss.
8. Brick of Chicago
Brick of Chicago is more than just Chicago’s best Instagram account (per the Chicago Reader’s readers’ choice awards): it’s also an opportunity to learn more about the city’s neighborhoods and the diverse bricks and people that built them. Join brick enthusiast Will Quam for a virtual tour via Zoom, starting at just $8. Recent virtual tours have included brick histories of Rogers Park, Washington Park, and Hyde Park, and some tours come with downloads of a map and Quam’s notes so you can see the sights for yourself on your own schedule. (Keep an eye out for in-person tour options when the pandemic and weather allow.)
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This “pay-what-you-like” operation offers walking and architecture tours to suit everybody’s interests, and is slowly resuming in-person tours, too. (Check their site for the latest availability and updates.) Whether you opt for a tour that’s led by a human or by GPS audio narration on your phone, you’re in for an entertaining and informative tour of Lincoln Park’s gangster history, of ghosts and hauntings downtown, and more. (While keeping the tour free is a totally valid option at checkout, it might be polite to throw a few bones at your guide.)
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Chicago’s top-ranked walking tours (per TripAdvisor) have moved entirely online in light of the pandemic, but that doesn’t diminish the slew of fun facts and historical insights that Chicago Detours brings to the table. Every tour is led by an experienced guide with a background in history, architecture, and/or art history, who dives into topics such as A Deep Slice of Chicago Food History, Innovations at the 1893 World’s Fair, and a Cruise from Your Couch Boat Tour. Tours typically range from $15–$18.
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