Exploring Chi-town
The sights, sounds, eats, drinks, and possibilities for fun and frivolity in Chicago are virtually limitless. As such, we've curated the following list of Chicago musts — from iconic attractions to award-winning restaurants, along with a wealth of options located within walking distance or a short car (or L) ride from the Hilton Chicago. Check out this helpful link for information on navigating Chicago’s various transit systems, including a convenient accessibility guide with details on getting around Chicago for those with special mobility needs.
Sights and Sounds | Food and Drink | Shows and Events | History and Design
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Be wowed by city sights
Grant Park
Proudly referred to as "Chicago's Front Yard," Grant Park totals 313 acres and is located in Chicago’s central business district, just one block from the Hilton Chicago. A city centerpiece much like New York’s Central Park, Grant Park is home to some of Chicago's most iconic landmarks and attractions. The park includes the Chicago Museum Campus, the Art Institute of Chicago, the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium, along with a portion of Millennium Park. Grant Park's centerpiece is the Clarence Buckingham Memorial Fountain, built in 1927 to provide a monumental focal point while protecting the park's breathtaking lakefront views.
Chicago Museum Campus
The setting of the Museum Campus couldn’t be lovelier — three Beaux-Arts-inspired buildings perched on the shores of Lake Michigan. Surrounded by lush parks and gardens, the Field Museum, Shedd Aquarium, and Adler Planetarium (the oldest planetarium in the Western Hemisphere, by the way), sit side by side, beckoning lovers of ancient civilizations, undersea worlds, and amazing universes.
A couple of things not to be missed: Máximo the Titanosaur (the largest creature ever known to man) and SUE the T. rex at the Field Museum; sharks, belugas, stingrays, sea otters, and sea lions at the Shedd; and high-powered stargazing at the Adler’s "Doane at Dusk."
Millennium Park
Located in the heart of downtown, Millennium Park is home to the iconic Cloud Gate statue (aka “The Bean”), interactive fountains, tranquil gardens, free events, public art, skating rinks, rock climbing, and plenty of green space.
Millennium Park offers a busy calendar of public events all year round, including the beloved Summer Music Series and Summer Film Series, when you can grab a seat on the Great Lawn and enjoy a free show under the stars. The park is also home to annual festivals, including the Grant Park Music Festival, the Chicago Blues Festival, the Chicago Jazz Festival, and Chicago Gourmet. In the summer, the park also hosts outdoor workouts, including free yoga, Pilates, Zumba, and tai chi classes.
Navy Pier
Navy Pier is a must-see Chicago destination. This family-friendly attraction has endless options for things to see and do, including scenic boat rides, summer fireworks displays, local food favorites, the largest rooftop bar in the country, free outdoor music, indoor gardens, carnival rides, and so much more.
The Centennial Wheel at Pier Park is one of Navy Pier’s most recognizable sights. This nearly 200-foot ride, inspired by the world’s first Ferris wheel that debuted at Chicago’s World Fair, consists of climate-controlled gondolas that take you soaring above the lakefront. Another favorite: summer fireworks displays every Wednesday and Saturday from Memorial Day to Labor Day. They’re especially jaw-dropping when watched from the deck of one of Navy Pier’s many cruise boats.
Other options when visiting the Pier: Catching a play at Chicago Shakespeare Theater, enjoying live music in the Navy Pier Beer Garden, having a cocktail at Offshore Rooftop, and exploring the Chicago Children’s Museum.
Chicago Observation Decks
Chicago boasts two adrenaline-pumping observation deck experiences, located in two of the city’s tallest skyscrapers. Skydeck at Willis Tower (formerly Sears Tower) invites you to literally step out on The Ledge, or rather a glass box that extends approximately 4 feet from the skyscraper’s facade, over 1,300 feet above ground level. TILT at 360 CHICAGO, located at 875 N. Michigan Ave. (formerly the John Hancock Center), tips you out and over The Magnificent Mile, and affords views of the city and Lake Michigan from 1,000 feet up.
Chicago Zoos
The Chicago area is fortunate to have not one, but two award-winning zoos. The Lincoln Park neighborhood is home to the Lincoln Park Zoo, one of the oldest and largest free zoos in the country, set in a scenic lakefront park. And nearby, you’ll find the Brookfield Zoo, another large zoo known for family-friendly events and cutting-edge animal care and conservation.
Soldier Field
Soldier Field may be best known as the home of the Chicago Bears, but the surrounding parkland also boasts a children's garden, the Soldier Field Colonnades (open and accessible to the public year-round), the Memorial Water Wall, and much more.
Chicago Riverwalk
Whether you’re in the mood to relax, party it up, or soak in the culture, the Chicago Riverwalk encompasses a variety of interests and experiences rolled into one. Sip wine on a riverside patio, or go island style under a canopy of light-strewn trees. Kayak the Riverwalk’s skyscraper canyon, take an architectural boat tour, or kick back on a tiki party boat. Visit a working bridgehouse and view the largest video-projected artwork in the world at Art on theMART. You can even immerse yourself in nature with a bit of pier fishing and birdwatching, right in the heart of downtown Chicago.
Chicago Beaches
Chicago is home to miles and miles of stunning lakefront beaches. Let the kids run and play at Foster Beach, rent a beachfront cabana at North Avenue Beach, or enjoy the skyline views at Rainbow Beach.
If you’re looking to get active on the water, you can rent a jet ski, kayak, paddleboard, or flyboard from Chicago Water Sport Rentals at 31st Street Harbor. Or embark on a kayak tour or paddleboard class with Urban Kayaks at Monroe Harbor.
Chicago's Vibrant Neighborhoods
Chicago is a city of unique neighborhoods, so no visit is complete without checking out one of its diverse enclaves. Each neighborhood has its own distinct culture, history, and vibe, so visitors are guaranteed to find one to spark their interest. Explore cultural history in Bronzeville or Chinatown, dive into the local dining scene in Logan Square or Pilsen, or surround yourself with nature in Lincoln Park or Garfield Park. No matter which you choose, you’ll get a slice of authentic Chicago life and spend the day living like a local.
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Eat and drink the best of the city
Lou Malnati's
Considered the oldest family name in Chicago pizza, Lou Malnati’s is a legend. It’s also a Chicago-based chain with a unique, ultra-crisp, buttery, and pie-like crust, which is crumbly and thin at the edges. If you order one with sausage (you should), be prepared to encounter a disc of meat on top that spans the entire pizza, covered in a fresh and chunky layer of tomatoes. If you’re a visitor to Chicago and ask for recommendations, be prepared to hear about this place from almost everybody, as its ubiquity means it’s a very nostalgic place for many people. There are many locations, ranging from take-out-only counters to large, shiny full-service restaurants all around the city.
Pequod's
Pequod’s looks and feels like an old dive bar, but step inside and you’ll find a pizzeria packed with both native Chicagoans and visitors alike. The pies are technically pan pizzas, which have a thicker bottom crust with a crispy, greasy fried texture to it. Pequod’s is best known for the dramatic halo of toasty, nearly blackened cheese around the rim of its pies. The house specialty sausage pie is definitely the way to go; Pequod’s sausage pieces are the size of gumballs and are plentiful and juicy.
Al's Italian Beef
The purported origins of the Italian beef sandwich can be traced back to this Taylor Street stand in Little Italy. That’s where Al Ferrari and family set up shop in 1938 and started popularizing what would become one of the city's most iconic foods. Today, the original location is still in business, and the beef remains unchanged — marinated in secret spices and dipped in gravy. So stop in, assume the proper upright eating stance, and savor a bit of Chicago history.
Jim's Original
The legend of "Jim's Original" started over 80 years ago, with a young, bright-eyed immigrant named "Jimmy" and a hot dog stand he has made literally "World Famous." Established in 1939, Jim's Original is the longest operating hot dog stand in Chicago. Jim's has been serving up the Original Maxwell Street Polish Sausage Sandwich for over 82 years, made today as it was back when Jimmy first "invented" it in 1943 — with sweet grilled onions and a smear of mustard. Visitors to Jim's can agree, there has never been a pleasure as great and as simple as taking a bite into one of Jimmy's original sandwiches.
Kindling | Downtown Cookout & Cocktails
James Beard Award-winning chef Jonathon Sawyer has taken on the project of creating what might be Chicago’s most opulent Italian beef. The $26 sandwich takes each component to its most over-the-top form, with beef sourced from a boutique farm in Georgia and bread from 3D Baking, a well-regarded local commercial bakery. Chicago’s famed J.P. Graziano’s makes the giardiniera, and those who like to gild the lily can add “raclette whiz” for a slight upcharge.
Monteverde
The first restaurant from former Top Chef and Spiaggia chef Sarah Grueneberg has quickly cemented itself as one of Chicago’s top Italian destinations. The pastas are the stars at this West Loop hot spot, and customers can see cooks hard at work behind the counter rolling out dough and creating the delectable noodles. The restaurant’s pandemic takeout menu remains, but the dining room offers lively options like whole-bird chicken Parm. There’s also a notable gluten-free menu.
Girl & the Goat
As one of the first restaurants on Chicago’s famed Restaurant Row in the West Loop, Stephanie Izard’s Girl & the Goat began in 2010 with a goal of serving bold, global flavors to the local community (and visitors!). The Goat's menu is divided into three categories: vegetable, fish, and, of course, meat. Bread is baked daily, and there are always new creations on the menu. Girl & the Goat sits in the West Loop smack dab in the Randolph Restaurant Corridor, but the location is still gritty enough to appeal to the chef’s integrity. They feature their own blended wine, along with a selection of beers on tap — and if you're lucky, you might come across the elusive collaboration beers that Stephanie personally crafted with a couple of beer buddy cohorts. Girl & the Goat accepts reservations but always welcomes walk-ins, nomads, adventurers, and those of you who don’t like to plan.
Manny’s Cafeteria & Delicatessen
Corned beef is a big deal in Chicago, and one visit to Manny’s and you'll understand why. A South Loop institution since 1942, thanks to its massive and delicious corned beef and pastrami sandwiches, an array of homestyle side dishes, and a family-friendly atmosphere cultivated over generations. The cafeteria-style setting is plastered with decades-old newspaper clippings and letters from Chicago luminaries. The space also houses a new wing for bagels, sweets, coffee, and food to go. In its heyday, Manny’s was where Chicago politicians were often seen brokering deals.
Harold’s Chicken
There’s fried chicken, and then there’s Harold’s fried chicken. The famed chicken shack has been serving locals since 1950, and is now a Chicago institution with locations throughout the city. Lucky for us, Harold's Chicken #62 is located less than a block from the Hilton Chicago. Make sure to order your chicken with Harold’s famous mild sauce.
Harry Caray’s Italian Steakhouse
Filled with Chicago memorabilia, Harry Caray’s serves up thick, aged prime steaks, chops, and classic Italian dishes with a Chi-town twist. Order the “best Chicken Vesuvio in the city” (according to the Chicago Tribune), featuring half a bone-in chicken, roasted with quartered potatoes, sweet peas, garlic, and white wine.
Twin Anchors Restaurant & Tavern
Among barbecue restaurants, Twin Anchors Restaurant & Tavern is one of the city’s oldest (established in 1932) and best (having received a Bib Gourmand award from the esteemed Michelin Guide). Located in historic Old Town, the quaint neighborhood tavern is best known for its tender, barbequed baby-back ribs and acclaimed homemade chili.
88 Marketplace
Chicago has many food halls, but none offer the same type of experience as 88 Marketplace, the Chinese grocer in East Pilsen. The grocery store stocks tons of ingredients not readily available at chain supermarkets (which alone makes it a destination), but the second-floor food court is also a culinary wonder not to be missed — including 312 Fish Market, a sit-down restaurant with one of the most creative (and affordable) sushi menus in town. You'll also find dumplings and other delights from A Place in Northeast, along with barbecue duck and more from BBQ King 88.
Carnitas Uruapan Restaurant
Chicago’s Mexican community and food enthusiasts worldwide flock to this longtime family-owned institution in Pilsen that celebrates all parts of the pig. Order carnitas by the pound at the front counter and settle into a table — if one is available — to craft your own individual tacos with a mix of salsas, tortillas, and beans ... or order tacos, soup, and cactus salad ready-made. Do note, you'll want to prepare for lines and waits during peak weekend hours.
Smyth
John and Karen Shields have brought their vision to life in Chicago, pushing fine dining boundaries and delivering an extravagant tasting menu. The techniques, ingredients, and service are all top notch, and they are one of a handful of restaurants that have attained a full three-star rating from the Michelin Guide. Developing close relationships with purveyors all over the Midwest, Smyth dishes out creative dishes with fantastic produce in one of Chicago’s most expensive meals.
Rose Mary
Joe Flamm and his partners went big in Fulton Market, opening a meticulously designed restaurant that’s become a destination for out-of-towners who know Flamm from his Top Chef win. But Rose Mary, described as “Adriatic drinking food,” is also locally beloved for its European culinary creations that fuse Italian, Croatian, and Midwestern sensibilities. The pastas would be at home at Spiaggia, one of the best Italian restaurants in Chicago before it closed, where Flamm cut his teeth. Try the cevapi, a Balkan-style sausage, or the octopus, cooked over a wood grill to perfection. There’s a great energy in the restaurant, which also offers a seasonal tasting table during the warmer months. Reservations are a must for the latter.
Ever Restaurant
It’s so synonymous with fine dining that a semi-fictionalized version of the restaurant had a starring role in seasons 2 and 3 of The Bear. Unlike the end of season 3 of The Bear, the real Ever continues to serve patrons. Chef Curtis Duffy became a superstar when he opened his first award-winning restaurant, Grace, on Randolph Street. Now he’s brought that energy a few blocks west to Fulton Market, where Ever opened in 2020. Duffy is offering only one tasting menu (vegetarians will be accommodated), but he remains committed to showing off precise techniques with playful execution. Case in point: artfully cut ribbons of freeze-dried hamachi. Fine dining tends to be polarizing, but for folks who want a meal with a dash of theatrics, Ever fulfills that niche better than any Chicago restaurant. Just note that this is one of the most expensive meals in Chicago.
The Berghoff
Beer and brats are Chicago staples, and The Berghoff serves some of the best. This family-owned restaurant has been in business since 1898 — an era when a beer cost a nickel and came with a complimentary sandwich on the side. Another historical nugget: The Berghoff obtained the first liquor license in Chicago after Prohibition ended.
Miller's Pub
A Chicago institution, Miller's Pub has been serving up traditional American grub and craft brews since 1935. Once one of the most famous late-night spots Chicago had to offer, where on any night of the week you might find Marilyn Monroe, Mayor Daley, or Chicago baseball legends Bill Veeck and Harry Caray in a booth next to you. Every day thousands of customers visit the multi-level restaurant and bar to enjoy its extensive menu of American cuisine and nostalgic ambiance, accentuated by dark wood, stained glass, and a huge collection of vintage oil paintings. Be sure to check out the numerous photos of Hollywood movie stars, professional athletes, Broadway actors, musicians, and local politicians who have frequented Miller’s over the years.
Moody Tongue Brewing Company
Based in the South Loop neighborhood of Chicago, Moody Tongue presents a selection of chef-driven beers and beer-centric dining experiences. Their Chicago-based production brewery offers beer selections available across a number of states and international cities. The Dining Room at Moody Tongue presents an intimate fine dining experience showcasing a 15+ course tasting menu with curated beer pairings. Or visit the bar for a lively tasting room and restaurant, featuring a la carte menu items as well as a collection of seasonal, perennial, and specialty beers.
The Green Mill
Want to get a glimpse of where Al Capone once hid his bootlegged booze? The Green Mill was Capone's favorite hangout back in the day, when he’d swirl a cocktail and listen to live jazz. His pal, "Machine Gun" McGurn, part-owned the club, which was central to their bootlegging operation. If it’s not too busy, ask the bartender to show you the trapdoor behind the bar that leads down to tunnels where they hid the hooch.
The Art Deco décor hasn't changed much since the 1920s. Seasoned bartenders will shake up a Sidecar or Manhattan or pop open a Pabst for you. But they're best known for their Martini: a crystal-clear, up-with-two-olives, non-fancy-pants, gin bracer. Order that Martini in the afternoon, and it'll be you and a handful of grizzled regulars minding their own business in the dim light. At night, the crowd sharpens, and you'll be drinking alongside serious jazz-heads who will shush you for talking during the sets. Imbibe on a Sunday, and poets will be your companions. The Green Mill is the birthplace of the poetry slam, still held each Sunday evening, which explains why much of the bathroom graffiti is written in verse.
As for sitting where Capone sat, you really can do that, too. His booth is the one at the end of the bar, on the north side — the only seat in the house that has a view of both doors.
Hello Jasmine
Voted Yelp’s #1 Fried Chicken in Illinois, Hello Jasmine is a local staple for authentic boba tea and Taiwanese food. After moving to Chicago from Taiwan, the founders were determined to create Taiwanese bento, snacks, and bubble tea that deliver the exact flavor they grew up loving. They pride themselves in producing genuine Taiwanese dishes and drinks by sourcing high-quality, "real" ingredients responsibly — including loose-leaf tea and brown sugar imported from Taiwan, fresh fruits, and the finest tapioca pearls. Their freshly brewed teas and slow-cooked bubbles are made by the staff daily, along with their celebrated Taiwanese bentos (a lunch box that typically includes protein, vegetables, and rice).
The Original Rainbow Cone
They say “Life’s too short for just one flavor.” The Original Rainbow Cone is a Chicago institution whose signature namesake treat is a cone stacked with slices of orange sherbet, pistachio, Palmer House (New York vanilla with cherries and walnuts), strawberry, and chocolate ice cream. Try the ultra-photogenic treat at Rainbow Cone’s original Beverly location or their Navy Pier outpost.
Garrett Popcorn Shops
Circa 1949, you could have found Gladys Otto, Garrett Popcorn Shops founder, selling bags of flavored popcorn for 5 cents a bag on the streets of Chicago. Today, these treats are still made in copper kettles, much like they were three generations ago. In addition to Buttery and Plain, Garrett’s handcrafted recipes also include Spicy CheeseCorn and four different CaramelCrisp recipes in Pecan, Macadamia, Cashew, and Almond. Don’t pass up trying their best-selling, world-famous Garrett Mix: an addicting mix of cheddar and caramel popcorn.
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Attend iconic shows and events
Chicago Cubs at Wrigley Field
Catch a game at one of America’s most famous ballparks! The Chicago Cubs have a full week of home games scheduled that just so happen to coincide with this year's AG schedule.
Built in 1914, Wrigley Field is the second oldest Major League baseball field in America. Throughout its history, the ballpark has witnessed countless historic moments — from Babe Ruth “calling his shot” in 1932, to “reversing the curse” in 2016. Not to mention, the Cubs have won three World Series titles and longstanding traditions are a key part of the experience.
So if you're a Cubs, Cardinals, or Guardians fan (or just a fan of baseball in general) get your tickets now!
Live Sketch Comedy: The Second City’s 113th Mainstage Revue
The Second City’s 113th Mainstage Revue This Too Shall Slap is a wild sketch comedy show that spins the familiar into the absurd … and makes the absurd feel oddly familiar. Performed by a hilarious six-person ensemble who specialize in chaos, charm, and comedic whiplash, this show will keep you laughing, guessing, and possibly questioning your entire reality.
Teatro Zinzanni
Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls of Spiegeltent ZaZou. Delight in premium cuisine, mesmerizing circus acts, and unparalleled entertainment unlike anything you’ve ever seen. This unforgettable show is an original form of entertainment combining a unique fusion of cirque, comedy, cabaret, spectacle, and live music, all while serving up a multi-course feast. Experience the allure of the Belgian antique Spiegeltent, where the past and present merge to create an unforgettable journey into the heart of entertainment.
Always...Patsy Cline
Besides being a delightful tribute to the renowned country singer, "Always..." is based on the true story of the friendship between Patsy and her most devoted fan, Louise Seger. One of the most popular stage musicals in the country, the heartfelt show has enjoyed great success all over the United States, including a successful run off-Broadway.
The musical is filled with down-home humor, true emotion, and the story of a relationship that any fan would dream of having with their idol. It features many of Patsy's unforgettable hits, including "Crazy," "I Fall to Pieces," "Sweet Dreams," and "Walkin' After Midnight." That's 27 songs in all, with a six-piece band on stage.
Summer Festivals and Events
Chicago SummerDance: Learn to salsa, waltz, swing, and more during these free, open-air dance lessons paired with live music in city parks.
NASCAR Street Race Weekend: NASCAR returns for two full days of action-packed racing, musical performances, family-friendly activities, and so much more throughout iconic Grant Park.
Millennium Park Summer Film Series: Watch free movies under the stars at this beloved summer event, screening family favorites, cult classics, and beyond.
Millennium Park Music Series: Grab a spot on the grass and enjoy free weekly concerts by local and national artists.
Chicago Craft Beer Festival: Dive into the city’s craft beer scene at this long-running fest in Lincoln Park, where you’ll find sips from more than a dozen local spots.
Grant Park Music Festival: This 80-year tradition brings free classical music to Millennium Park all summer long.
Jazzin’ at the Shedd: This weeknight series features a festival-worthy lineup of Chicago’s top jazz ensembles, along with access to the aquarium, cocktails, and unbeatable city views.
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History and design unlike any other
Griffin Museum of Science and Industry
Located in Jackson Park on Chicago’s South Side, the Griffin Museum of Science and Industry is not only one of Chicago’s most popular attractions, but one of the largest science museums in the world. Filled with endless interactive exhibits about science, innovation, and engineering feats from around the globe and throughout history, the museum features popular permanent exhibits including the Coal Mine, U-505 Submarine, and the Mirror Maze, with exciting new temporary exhibits added each year. Be sure to block out an entire morning or afternoon to visit — the museum is massive!
Museum of Contemporary Art
Unlike the Art Institute of Chicago, the Museum of Contemporary Art features constantly rotating exhibitions by contemporary artists. This museum is family-friendly, but students and adults may especially appreciate the more nuanced, and often heavier, subject matter. Still, there is artwork for everyone to enjoy. The museum also offers live performances, events, and programs for the community. Expect to spend around an hour to two here, at least.
Chicago Children’s Museum
At the Chicago Children’s Museum, children of all ages can enjoy a space to play and learn. Located at the Navy Pier, the museum itself is comprised of more than a dozen exhibits that cater to different interests and experiences. Exhibits like Tinkering Lab, Skyline, and Dinosaur Expedition will allow children to tinker, build mini-skyscrapers, and even dig for dinosaur bones. At the Art Studio, children can let their imaginations soar with painting, drawing, and pottery-inspired workshops.
Additionally, children can learn practical life skills and take the lead at exhibits like Kids Town and Michael’s Museum. And for some overall fun, there are tons of exhibits for your little ones to climb, play, explore, and learn.
Chicago History Museum
Located near the lake in the southeastern corner of Lincoln Park is the Chicago History Museum. One of Chicago’s oldest cultural institutions, a visit to this museum will walk you through the city’s historic past to learn about what makes Chicago, well, Chicago.
Exhibitions explore topics like freedom, democracy, and the history of Chicago. A film is also available to learn about the city’s growth and events like the Great Chicago Fire of 1871. There’s even an exhibit for uncovering the city through the five senses.
Jane Addams Hull-House Museum
Hull-House, Chicago's first social settlement, was not only the private home of Jane Addams and other Hull-House residents, but also a place where immigrants of diverse communities gathered to learn, to eat, to debate, and to acquire the tools necessary to put down roots in their new country.
A National Historic Landmark, free and open to the public, the Jane Addams Hull-House Museum hosts exhibitions and programs that connect histories of social transformation to the present. For the University of Illinois Chicago and for national and international visitors, the museum endures as a site of activism, creative expression, research, and education.
Richard H. Driehaus Museum
Located just steps from The Magnificent Mile, the Richard H. Driehaus Museum explores the art, architecture, and design of the late 19th-century with a focus on the Gilded Age. The exquisite building was saved twice, first by a collective of over 100 Chicago citizens in 1919, and then by philanthropist Richard H. Driehaus, who sponsored its restoration from 2003-2008.
The Driehaus Museum engages and inspires the global community through exploration and ongoing conversations in art, architecture, and design of the late nineteenth and early twentieth centuries. Its permanent collection and temporary exhibitions are presented in an immersive experience within the restored Nickerson Mansion, completed in 1883, at the height of the Gilded Age, and the 1926 Murphy Auditorium. The Museum’s collection reflects and is inspired by the collecting interests, vision, and focus of its founder, the late Richard H. Driehaus.
Chicago Architecture Center
Get double the architectural history at One Illinois Center! Not only was it designed by Ludwig Mies van der Rohe, but it’s also the location of the Chicago Architecture Center, the perfect starting point for your discovery of Chicago’s downtown architecture. Enter through the main doors and you’ll have your pick of over 85 walking, bus, and boat tours.
Wander up one level for the main attraction, "Building Tall" in the Skyscraper Gallery. Towering scale models of the world’s most famous skyscrapers frame views through massive windows onto, well, some of the world’s most famous skyscrapers. The center is located above the Chicago Riverwalk, with a dedicated dock for the center’s signature Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady.
Frederick C. Robie House
An iconic landmark in terms of Chicago architecture and design, the Frederick C. Robie House was designed by famed Chicago architect Frank Lloyd Wright and is best known for showcasing his Midwestern Prairie-style.
Built in 1910, it’s now a museum where you can witness this Prairie-style architecture up close. Tours show off the exterior and interior, including its unique woodwork. The house is also located on the University of Chicago’s campus, so be sure to wander around for more unique architectural sights.
The Rookery Building
Hailed as one of Chicago’s coolest buildings, the Rookery Building is a stellar example of the city’s architectural boom that followed the Great Chicago Fire of 1871. Considered by many to be an “architectural masterpiece,” the building itself was designed by Daniel Burnham and John Root. However, Chicago architect Frank Lloyd Wright had his hand in redesigning the lobby in 1905.
Historic Water Tower
With a detailed Gothic Revival facade, Historic Water Tower bursts with charm. It was built as part of Chicago’s municipal water system, originally housing a 135-foot iron standpipe used to regulate water pressure, and one of the few city structures to survive the Great Chicago Fire. Today, it’s the City Gallery at Historic Water Tower, and the place to go for free rotating art exhibits. The original pumping station, another survivor of the fire, is just across the street.
Tribune Tower
The Tribune Tower is a striking Gothic Revival tower that formerly housed the Chicago Tribune newspaper. Made of Indiana limestone, the design incorporates Art Deco, Medieval, and French-cathedral-inspired details.
The building’s first story walls are embedded with roughly 150 fragments from the world’s most important historic buildings and sites, including the Berlin Wall, the Winter Palace in Beijing, Westminster Abbey in London, the Great Pyramid in Giza, and the Parthenon in Athens.
The Monadnock Building
The Monadnock Building (historically the Monadnock Block) is a 16-story skyscraper located at 53 West Jackson Blvd. in the south Loop area of Chicago. The north half of the building was designed by the firm of Burnham & Root and built starting in 1891. At 215 feet, it is the tallest load-bearing brick building ever constructed. It employed the first portal system of wind bracing in the United States, and its decorative staircases represent the first structural use of aluminum in building construction. The later south half, constructed in 1893, was designed by Holabird & Roche and is similar in color and profile to the original, but the design is more traditionally ornate. When completed, it was the largest office building in the world. The success of the building was the catalyst for an important new business center at the southern end of the Loop.
Pullman Historic District
Take a trip back in time with a stroll through the charming streets of the Pullman Historic District. The first planned industrial community in the U.S., the Pullman neighborhood is a hidden gem known for its innovative urban design and stunning architecture. The area was designated a National Monument by President Obama in 2015, making it Chicago’s first and only unit of the National Park System.
The neighborhood was meticulously planned by George Pullman in the 1880s as housing for employees of his Pullman Palace Car Company. Today, visitors can stop by the Pullman Factory where the railroad cars were constructed, the Hotel Florence, named for his daughter, and the A. Philip Randolph Pullman Porter Museum, which documents the first African American labor union in the country.
The Last Wooden Street in Chicago
Before the Great Chicago Fire, many of the city’s streets were made of wood and covered with tar. But after the fire set streets aflame, wooden blocks fell out of favor. The last remaining wood-paved street is located between Astor and State Streets, behind the sprawling mansion of the Archbishop of Chicago. Walk through the alley’s 919 square yards, which were restored and placed on the National Register of Historic Places in 2002. After, you can explore the rest of the Astor Street District, which boasts historic 19th-century houses that make up one of the city’s most affluent neighborhoods.
