Chicago's downtown skyline

Architecture Tours in Chicago

Art Deco architecture, mid-century Modernism, beautiful Beaux-Arts buildings and early examples of the skyscraper: you’ll find it all in the Windy City.

Chicago is a treasure trove of architectural marvels, from century-old riverside skyscrapers and Frank Lloyd Wright masterpieces to movable bridges and the eye-popping sculptural showpieces by Anish Kapoor and Frank Gehry in Millennium Park. Read on for our guide to seeing all these and more on Chicago’s top architectural tours.

Shoreline Architecture River Cruise

Sightseeing river cruise

Shoreline Architecture River Cruise

There are few better ways to get a broad overview of Chicago’s architectural significance than on a cruise of the shoreline. This sightseeing boat ride covers three branches of the Chicago River, taking in skyline icons like the Willis Tower, Jeanne Gang’s shimmering Aqua skyscraper, and the distinctive Spanish Colonial Revival Style of 1920s stalwart the Wrigley Building. Along the way, you’ll learn how Chicago rebuilt after the Great Fire of 1871, see how its architecture has evolved over the years, and hear about the city’s pioneering approach to skyscraper construction in the late 19th and early 20th centuries. There will also be a photo opportunity or six at historic Wolf Point.

Movable bridge on the Chicago River

Top tip #1: If you’re in the market for something a bit more in-depth, the Chicago Architecture Foundation cruise is a good bet. This one’s led by bona fide architecture experts who should be able to answer all your most pressing questions about the city’s prevailing styles, as well as ticking off the feats of engineering innovation that led to Chicago having more movable bridges than any other city on the planet.

Top tip #2: the standard shoreline architectural sightseeing cruise is included with a pass from Go City, which can save you up to 50% on entry fees when sightseeing in Chicago and also includes access to several Frank Lloyd Wright attractions, plus the Field Museum, Shedd Aquarium and more. It also includes a guided tour of Chicago’s Riverwalk, which gets you even closer to downtown titans including the Tribune Tower and Jewelers Building, once the tallest building outside of NYC.

The Loop Walking Tour

The Willis Tower viewed from Lincoln Park

The Loop Walking Tour

Book a guided tour or go it alone on a self-guided walk of the Chicago Loop in the heart of downtown. Here’s where to get up close to some of the city’s best-loved architectural masterpieces. We’re talking the likes of the Willis Tower with its space-age modular design, which held the record of world’s tallest building for nearly a quarter-century before Malaysia’s Petronas Towers took the title in 1996. Then there’s the Chicago Cultural Center with its distinctive Tiffany glass dome, the Rookery with its Frank Lloyd Wright-designed atrium, and the Monadnock Building, a monolithic early skyscraper, built way back in the 1890s. At 215 feet, the Monadnock remains the tallest load-bearing brick building ever constructed. They don’t make 'em like they used to.

Frank Lloyd Wright Home and Studio Tour

Inside the Frank Llloyd Wright Home and Studio
Image: Frank Llloyd Wright Home and Studio

Frank Lloyd Wright Home and Studio Tour

Visionary architect Frank Lloyd Wright lived and worked here in Oak Park Chicago for 20 years at the turn of the 19th Century, in the home he himself designed for his growing family. As well as fathering children (six of them!), this is also where he developed his trademark Prairie Style. Among the 125-or-so buildings he and his associates designed here are the nearby Unity Temple and Robie House (of which more below). Take the 60-minute house tour that’s included with the Go City Chicago pass for an in-depth insight into Wright’s life and works. The museum also offers self-guided audio tours of the neighborhood, including the Unity Temple and many other buildings that were influenced by his vision.

Robie House Tour

The Robie House
Image: The Robie House

Robie House Tour

Considered one of the most important buildings in the history of American architecture, the Robie House exemplifies Frank Lloyd Wright’s vision of the Prairie Style home, a style that emphasizes the use of horizontal lines and open spaces that blur the boundaries between interior and exterior zones. Step inside to eyeball the amazing geometric interiors of this 1910 Wright masterpiece and learn all about the building’s history and recent restoration on a guided tour.

The Robie House’s location in the residential Hyde Park neighborhood also makes it a good springboard for a self-guided exploration of the South Side, where you can also ogle the historic Italianate and Colonial Revival mansions in Kenwood.

Historic Skyscrapers Tour

The Carbide and Carbon Building in Chicago

Historic Skyscrapers Tour

Chicago led the world in skyscraper construction, with its first (indeed the world’s first) high-rise going up in 1885. Run by the Chicago Architecture Center, this tour of the Windy City’s most iconic tall buildings calls at the site of the aforementioned Home Insurance Building (sadly no longer with us), plus the opulent Art Deco grandeur of the Carbide and Carbon Building (pictured), and the Reliance Building, one of the world’s first fully glazed high-rise buildings. Expect fascinating insights into Chicago’s early urban development, plus photo opps at some of the oldest steel-framed buildings on the planet.

Tour of Millennium Park

Anish Kapoor's Cloud Gate aka 'The Bean'

Tour of Millennium Park

No visit to Chicago would be complete without nabbing a selfie or six in front of (and underneath) Anish Kapoor’s extraordinary Cloud Gate sculpture, better known as ‘The Bean’. This huge gleaming icon creates twisted, ever-morphing reflections of the surrounding cityscape and its inhabitants. You’ll find it in Millennium Park, where Frank Gehry’s astonishing Jay Pritzker Pavilion is a futuristic vision in stainless steel and makes for a memorable venue for open-air concerts. Also in the Millennium Park neighborhood, Renzo Piano’s design for the Art Institute of Chicago’s Modern Wing is another fine example of modern architecture. And the collection within – Matisse, Picasso, Kandinsky, Dalí, Miró and more – is no less spectacular.

See Chicago for Less!

On the Skydeck at Willis Tower

See Chicago for Less!

If your appetite has been whetted by our round-up of top architectural tours in Chicago, you’ll be pleased to know that many of the tours mentioned above are included with a pass from Go City. The pass can save you up to 50% and includes entry to Frank Lloyd Wright attractions, plus a movie locations tour, the Skydeck Chicago observation platform at the Willis Tower, the Griffin Museum of Science and Industry, and more. Click the buttons below to find out more and choose your pass!

Stuart Bak
Stuart Bak
Freelance travel writer

Stu caught the travel bug at an early age, thanks to childhood road trips to the south of France squeezed into the back of a Ford Cortina with two brothers and a Sony Walkman. Now a freelance writer living on the Norfolk coast, Stu has produced content for travel giants including Frommer’s, British Airways, Expedia, Mr & Mrs Smith, and now Go City. His most memorable travel experiences include drinking kava with the locals in Fiji and pranging a taxi driver’s car in the Honduran capital.

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Things to do in Logan Square, Chicago

Looking for a cool place to stay in Chicago? Give Logan Square a go. This up-and-coming district is full of modern fun for any discernable customer. Let us tell you why! These are the best things to do in Logan Square, Chicago! Including: Logan Theater Logan Arcade Farmers Market Lincoln Lodge Rosa's Lounge and more! Catch a flick Suggesting a cinema visit might seem a strange suggestion for a vacation, but when your theater is named after the district you're in, and its sign is one of the area's most recognizable, that changes things somewhat. Inside The Logan Theater, you'll find multiple screens playing both big-budget blockbusters and lesser-known indie darlings. The sound and visual quality on offer are well known throughout Chicago, so you can expect an excellent experience when you go. Compound all that with the theater's lounge, where you can grab a drink or even catch a comedy show or pub quiz, and myriad midnight screenings of cult gems, and you've got yourself a nailed-on night out. Game on Want to put your friends and family to the proverbial digital sword? Take them down to Logan Arcade. Inside this repurposed hardware store, you'll find a number of excellent old-school arcade cabinets featuring nostalgic greats like Pac-Man, Q-Bert, and Street Fighter 2, as well as pinball machines themed around old films and games. Keeping the whole thing aloft is a fantastic bar with local craft beers, spirits, and cocktails to keep you refueled. And, if all that gaming gets you hungry, Fry Like An Eagle is in residency there, offering delicious vegan junk food to all and sundry. Farm to your table Do you long for fresher produce than your local supermarket? Do you want to give back to the local community? Are you planning on making your own meals while visiting Chicago? If you answered yes to some or all of these, go seek out Logan Square Farmers Market. Every Sunday, you'll find seasonal produce, fresh meats, delicious fruit and veg, and even some baked delights ready to be eaten! In warmer months, you'll find the market sprawled out to make the most of the sunshine. When things take a turn, they retreat into a nearby building. To the benefit of everyone, we're sure you'd agree. Get funny When they say laughter is the best medicine, are they insinuating that it's only needed by the sick and infirm? Something for you to ponder. In the meantime, leave your existential thinking at the door and enjoy some great comedy at the Lincoln Lodge! The self-proclaimed longest-running independent comedy shop in America, Lincoln Lodge host a number of improv, stand-up, and sketch performers every week. With previous luminaries including the likes of Hannibal Burress, you've every chance to find the next big thing when you go! Music and drinks Many things don't go hand in hand quite like music and drinks. So why not combine the two and head to Rosa's Lounge, Logan Square's premier blues club? For nearly 40 years, it's been the go-to for blues lovers who want to sit, sip a cocktail, and tap their foot to some old-school R&B. The real old-school R&B, not the synchronized dancing sort. This family-run joint has a rotation of regular acts throughout the week. However, every weekend, performers from across the country make the pilgrimage to play on the lounge's stage. So, if you want some great music to pair with a cocktail or two, give Rosa's Lounge a look in. Park hangs Let's move from inside to out, into the warm embrace of nature. Parks are the city dweller's escape from the concrete jungle, giving them the chance to touch grass and look at colors other than grey. Lucky for you, Logan Square has some great spots to sit down and take a breather. Humbolt Park may be a far cry from its original, animal-rich self, but there's still plenty of green to see and things to do. Take a tour of the lagoons, play a few sports on the available courts, go for a run on some of the back paths, or go see the Humboldt Boathouse for yourself. They don't make buildings quite like it anymore. Or, go for a walk around The 606. This disused railway track worms its way through parts of the city, giving you the chance to see many of Chicago's amazing landmarks. It's popular, mind, so you will not be alone. However, ignore the pedestrians and pretend you're an explorer in the post-apocalypse. Or something, you do you. Food for thought All that exploring's gonna get you hungry, there's no doubt. Thankfully, you've got some great spots that'll sort that rumbling tummy right out. Nothing beats pie, and nothing beats Bang Bang Pie Shop's pie. Sweet pies, savory pies, meat pies, veggie pies, they've got it all, along with a fantastic selection of freshly-made biscuits with just about whatever you want on them. Yes, please. Formerly acclaimed joint Fat Rice, Noodle Bird has now taken over. Offering up a delicious selection of Asian street food, it's as good on the go as it is at the table. Their signature dish is live-fire charcoal-grilled chicken, with an assortment of veg and rice. Pick up some canned wine while you're there, and pretend you're more sophisticated than you really are. How about some New American cuisine to make you feel even more sophisticated? Daises do just that, with a seasonal rotation of pasta dishes with a New American twist. And as a modern joint, you can expect vegetarian alternatives for each dish. Do yourself a favor and get the gnocchi. Sublime. Chicago Nights Let's end this list on the nightlife. Your last port of call when the daylight hours are dwindling. Surprising no one, Logan Square has a great selection of nighttime haunts to test out. Longman & Eagle is a hipster spot where you can expect '60s whiskey cocktails from Millennials with tattoos. It's a great spot to spend the night and strike up a conversation with the bar hands or patrons. And hey, why not make new friends in a new city? You never know when you'll be back. Another great cocktail spot is Scofflaw, which has a more colorful variety of drinks on offer. Their focus is gin, which is all the rage these days. Mother's ruin has become the go-to spirit of the millennial crowd. And with good reason. Or, have a dance and play a few rounds of Skee Ball at Slippery Slope, which has plenty of beers, cocktails, and LGBT-friendly nights to boot! And that's our list of the best things to do in Logan Square, Chicago!
Dom Bewley
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Things to do in The Loop, Chicago

You there! Are you visiting Chicago at some point in the future? Are you wondering which districts to check out during your visit? Do you like loops? Well, The Loop might just be the perfect place for you to visit during your vacation. Here are some of the best things to do while you're there! Including: Grant Park Shedd Aquarium Eat Drink Shopping and more! Grant Park Let's begin, then, with one of the city's most significant green zones; the one and only Grant Park! Named after the late, great Ulysses S. Grant, this behemoth of a park measures over 300 acres. Step inside, and you'll find a world of entertainment. Perhaps the park's biggest draw is Millennium Park, where you'll find Cloud Gate. Referred to locally as The Bean, this massive, chrome, reflective sculpture by artist Anish Kapoor is one of the most recognizable landmarks in Chicago, and has featured in many films and TV shows. But alongside The Bean, you'll find Buckingham Fountain, Maggie Daley Park, Art Institute of Chicago, The Court of the Presidents, and much more at Grant Park! The Field Museum Want to discover over 4 billion years of history in one place? Then you should check out the Field Museum! There, you'll meet Maximo, the largest recorded dinosaur ever found on Earth. Weighing in at over 70 tons, they were quite the beast! You can also experience what it's like to be a tiny bug at the Underground Adventure exhibit, observe scientists extract DNA in real-time at the DNA Discovery Center, and also watch fossils being prepared at the Griffin Halls of Evolving Planet. All that and much more await you at the Field Museum. So, what are you waiting for? The Art Institute of Chicago Let's get cultural for a second, and talk about some art. In The Loop, you'll find the Art Institute of Chicago, one of the best-known art museums on Earth! Inside, you'll find hundreds of pieces from all across the globe, from older, more traditional masterpieces to modern marvels. With fixed collections as well as a rotation of amazing seasonal experiences, there's sure to be something inspiring at the Art Institute of Chicago! Skyline Lake Tour Want to see the city from a different perspective? Check out a Skyline Lake Tour. Take to the seven seas, or just the one in this case, and enjoy amazing views of Chicago's heavenly skyline as you spot some of the city's biggest and best landmarks. Beginning at Navy Pier, your trip will take you past the likes of the Adler Planetarium, Field Museum, and beautiful Grant Park. And, with a learned robot, or prerecording, narrating the significance of each spot, you'll learn all about modern Chicago. American Writers Museum Words. Powerful, plentiful, and often misused, words are the backbone of our civilization. Want to discover how Americans have used words over the centuries? Then head to the American Writers Museum in The Loop. Novels, speeches, poetry, and more are all housed within. See how historical events changed the approach of American authors, whether through war, financial collapse, or in response to cultural shifts. Learn how speechwriters changed the course of history. And discover how American poets touched the hearts and minds of millions. With a huge variety of words in all their forms on display, you're sure to find something mind-opening at the American Writers Museum. Shedd Aquarium Next, let's take a trip under the very oceans themselves. At Shedd Aquarium, you'll find a whole new world of wonder in the heart of The Loop. See exotic species of marine life from all corners of the world, from sharks to stingrays, and plenty more too! There are a wealth of exhibits to explore within, including a 360-degree tour at the Caribbean Reef, a look at South American fish species that occupy the Amazon at Amazon Rising, and a look at how a local community saved their coral reef from being wiped out at Wild Reef. All that and more ocean fun awaits you. So go get your snorkel and suit up! Eat! After all the activity, you might be feeling peckish. Never fear; we've got your hunger covered. The Loop has plenty of places to eat a wide variety of cuisine. Can't decide which to pick? Head to Revival Food Hall, which houses a large number of food vendors under one roof. Whether you're in the market for pizza, seafood, or Italian, you're sure to find something to turn your head there! Want a little fusion in your life? Head to Saucy Porka, which mixes Asian delights with Latin deliciousness. Wonder what a bao bun would be like if it was filled with some fried meat and beans? Look no further. Or, if you just want a snack to refuel you during the day, stop by Gayle's Best Ever Grilled Cheese. Sure, it's simply a collection of grilled cheese sandwiches. But grilled cheese is good. And these are some of the best you'll ever taste. Drink! Need a little refreshment in The Loop, or looking for a quality night out? You're in luck, because there are some great spots in the area you should check out. Monk's Pub combines a medieval exterior and modernized interior, replete with a load of beers on tap and bites to sample. Want a little blues with your booze? Head to Buddy Guy's Legends, which combines foot-tapping tunes with a delightful selection of drinks. Or, if you're feeling super fancy and the weather is fine, check out a rooftop bar like Raised or Boleo. Whichever you pick, you'll find top cocktails, good vibes, and great views of the beautiful Chicago skyline. Shop! And finally, let's end our list on a little shopping spree. The Loop has a load of great boutiques where you can pick up some slick accessories, threads, and everything in between. Of course, there's Macy's, where you'll find a world of shopping bliss and pretty much whatever you need. But there are also specialized shops like Optimo Hats for all your headwear needs, Madison Hall for your continental clothing supplies, and Graham Crackers Comics if you're looking for some special editions. And that's our list of the best things to in The Loop when visiting Chicago. Enjoy!
Dom Bewley

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