Best Tours in Chicago

Chicago is known for its history, culture, architecture, and it's also full of many famous film locations. This tour is hinged on an idea to showcase the city's downtown via movies — an excellent experience for a movie buff! You'll start exploring the Chicagoan cinematic scenery from the Union Station, a railroad station used as a backdrop for a whole bunch of motion pictures. Continue with the Willis Tower, a set for the "Divergent" movie that invites you to see an aerial view of the city from Skydeck, an observation deck on the 103rd floor. Then, take a few selfies with Chicago's most notable public sculpture, the fabulous Cloud Gate, affectionately called "The Bean." From there, come over to spacious Daley Plaza and contemplate a whimsical "Untitled" sculpture by Pablo Picasso, another iconic emblem of Chicago. After that, you will pass by the Chicago Theater that сonceals a stunning ornate architecture inside, outshining its punchy neon sign. Another eye-catcher on the route is the Seventeenth Church of Christ Scientist, a distinctive building in the area with a supernatural exterior. Next, you will cross the bridge over the Chicago River to explore more buildings of concrete and glass that often get spotted in movies. Downtown Docks is the place to chill at the end of the tour. Lay back at the wooden benches watching Marina City and the river cruises passing under the bridges. Join the tour and imagine yourself being on a film set!

Embark on a journey through Chicago's awe-inspiring sights with this in-app audio tour, designed for enthusiasts of architecture and cultural vibrancy. With the ticket to Skydeck Chicago included, you'll start high above, relishing unrivaled urban vistas, and then gradually descend into the streets teeming with architectural marvels and historic tales. The tour begins at the majestic Skydeck Chicago atop Willis Tower and leads travelers on an enriching route through the city's iconic landmarks. You'll marvel at The Rookery Building's intricate designs, take in the public art prowess at the Chicago Picasso, and feel the cultural pulse at the historic Chicago Theater. Your self-guided itinerary ensures a memorable exploration of the Windy City's most captivating spots. From the grandeur of Buckingham Fountain to the towering presence of 875 North Michigan Avenue, your journey through Chicago is punctuated with moments of wonder. Remember, while you'll have an enlightening self-guided tour of Chicago's streets and sights, an audio tour inside Skydeck Chicago will not complement your visit there.

Satisfy your sweet tooth at the famous Museum of Ice Cream, in Chicago. Explore a sugary wonderland curated by experts in confectionary craftsmanship. Located within The Shops at Tribune Tower, this sugary paradise covers 13,500 square feet, making it a must-visit in Chicago. Enjoy a 60 to 90-minute tour through 14 delightful installations, indulging in sweet surprises along the way. Forget about your waistline worries and taste the irresistible treats (you only live once, after all). Take a ride on the Sprink-L line, try your hand at mini-golf, or jump into a pool filled with colorful sprinkles. Come hungry and leave with a newfound appreciation for the delicious world of taste and texture.

This self-guided audio walking tour explores Rosehill Cemetery through the lives, memorials, and monuments that shaped Chicago and the United States. It is ideal for travelers interested in local history, Civil War memory, architecture, reform movements, business leaders, and the quieter side of the city. The route begins at the Rosehill Cemetery Entrance in Chicago and leads you along a winding path past graves and monuments tied to early settlers, soldiers, inventors, artists, politicians, and nationally known figures. Along the way, you will encounter memorials to Union troops, the Chicago Board of Trade Battery Monument, the Horatio N. May Chapel, and notable resting places including Frances E. Willard, Charles Gates Dawes, Oscar Mayer, Elisha Gray, Ignaz Schwinn, Myra Bradwell, and John Wentworth. The walk ends at the grave of John Wentworth, former mayor of Chicago. By the end, the most memorable experiences will likely be standing among Civil War monuments, discovering how many famous Chicago stories meet in one peaceful landscape, and noticing the striking contrast between solemn stone memorials, grand funerary art, and the calm beauty of this historic cemetery.

This self-guided audio walking tour introduces first-time visitors to the heart of downtown Chicago. It is ideal for travelers interested in city design, architecture, public spaces, and the layered history hidden between busy streets and famous landmarks. Your route begins in the Chicago Pedway, the underground network of passages beneath the Loop, where tiled corridors, storefronts, and station connections reveal a lesser-seen side of the city. From there, you head to City Hall to see its grand neoclassical facade and the civic center of Chicago. The tour then leads you toward the Chicago River, where bridges, boat traffic, and canyon-like towers show why this waterway shaped the city’s growth. You continue to the gleaming white Wrigley Building and the Gothic crown of Tribune Tower before turning south toward Millennium Park and Cloud Gate. The walk ends in the Chicago Loop, the district that gave downtown its name and still pulses with trains, office towers, theaters, and sidewalks full of movement. Along the way, the most memorable moments include stepping from the dim Pedway into bright streets, looking up at ornate skyline details, watching the river cut through steel and stone, and seeing your reflection ripple across the polished curve of Cloud Gate.

This self-guided audio walk introduces first-time visitors to downtown Chicago through public art, river views, grand architecture, and the city’s lively waterfront. It is a great fit for travelers who want an easy-to-follow route with famous sights and a clear sense of how Chicago looks and feels on the ground. Your route begins at Cloud Gate in Millennium Park, where the polished steel surface bends the skyline, the trees, and your own reflection into a shimmering curve. From there, you head toward the Chicago Riverwalk to follow the water between tall towers and bridges, then dip into the Chicago Pedway, a hidden network beneath the busy streets above. The walk continues to Tribune Tower, where carved stones from world landmarks are set into the walls, and then along the Magnificent Mile, lined with storefronts, flags, and high-rises. The tour ends at Navy Pier on Lake Michigan, where the open water, the long boardwalk, and the Ferris wheel create a festive finish. Along the way, the most memorable moments include standing beneath the mirror-bright arch of Cloud Gate, hearing the river move under steel bridges, spotting Gothic details high on Tribune Tower, and reaching the lakefront where the city opens into sky and water.

Delve into the essence of Chicago on a riveting self-guided audio tour that will take you through 200 years of history along the iconic Chicago River. This tour is tailored for anyone with a curiosity about the city's vibrant past, architecture, and transformative milestones. It's an exploration of the river that has been the lifeblood of the city, attracting both settlers and tourists alike. Embarking from the historic McCormick Bridgehouse, you'll journey along a well-marked path, venturing through time from the early days of Chicago's first settler, to the hustle and bustle of its great 1800s harbor, and into the present day where the river is a centerpiece of urban delight. The endpoint of this revealing tour is at the prestigious Michigan Avenue, also known as the Magnificent Mile, renowned for its rich history and contemporary charm. As one traverses the route, visual treats along the way include impressive drawbridges, monumental buildings, and commemorative sites—each with its own story. You'll experience the unique wonder of watching the river glisten with emerald green on St. Patrick's Day and understand why Chicago holds such an esteemed place in America's narrative. By the tour's conclusion, not only will your footsteps have traced the ebbs and flows of time, but your mind will be awash with the sights and sounds of a city that has continued to reinvent itself while honoring its profound heritage.

Dive into Chicago's River North neighborhood with a self-directed audio walkthrough designed for urban adventurers eager to uncover the city's lesser-known treasures. This excursion offers a blend of Chicago's savory eats, vibrant street art, peculiar shopping venues, and sports legends, all crafted for those looking for an atypical journey beyond the usual sights. Starting at the Merchandise Mart, once the largest building in the world, the tour wraps up at the solemn Eastland Disaster Memorial. This audio guide leads you through a series of remarkable spots nestled in the urban landscape of River North. Travelers will engage with the haunting tales of the Old Chicago Historical Society, visit the birthplace of the deep-dish pizza, walk along the Chicago Riverwalk, and glimpse the Chicago sports legacy immortalized in handprints on La Salle Street. On this route, the pulsating heart and soul of the city are revealed in places like the Blues House, offering lively entertainment, and the vintage Reid Murdoch Building, showcasing Americana charm. This tour offers a chance to experience the city's dynamic spirit through your own eyes and curiosity, creating a memorable journey of Chicago's River North.

Delve into the enchanting streets of Chicago with this in-app audio tour, tailored for explorers keen to uncover the secrets of Streeterville, absorb the beauty of the Lakefront Trail, and indulge in the buzz of the Magnificent Mile. Perfect for anyone with a curious mind and a thirst for urban tales, this tour is your audio compass to the jewel of the Midwest. The journey begins at the bustling DuSable Bridge, gradually meandering through the historic Streeterville, alongside the sandy shores of Lake Michigan, and culminating amidst the grandeur of the Magnificent Mile, at the historic Green Door Tavern where mobsters used to hang out. Along the route, you'll be guided to iconic sites like the venerable Water Tower, the plush Oak Street Beach, and the towering John Hancock Building, all while unraveling the layers of Chicago's storied past. This walking expedition promises to paint pictures of disastrous shipwrecks, draw you into legendary battles, and place you in the footsteps of the city's most influential gangsters. By the end of this adventure, you will have not just traversed Chicago’s grand avenues but journeyed through the very history and heart that pulse beneath its surface.

Unlock the lesser-known tales of Chicago with an in-app audio adventure through the opulent Gold Coast neighborhood. History buffs and urban explorers alike will find themselves transported back in time to the Gilded Age, uncovering the city's affluent past and hidden gems along the way. This audio guide is not only a journey through space but also through time, offering an immersive experience into Chicago's yesteryears. The tour launches outside the Chicago History Museum and takes a winding path through Lincoln Park, the Couch Mausoleum, and along the grand streets of the Gold Coast. The route introduces travelers to the Playboy Mansion's secrets, a wood-block paved alley, and concludes with a melodious finale at Zebra Lounge—Chicago's oldest piano bar. Along the way, stops at mansions, historic sites, and alleyways reveal the hidden fabric of this storied neighborhood. Highlights of the journey include exploring the original Playboy Mansion grounds, walking down a 19th-century alley, and enjoying live piano music in an iconic bar. Each step echoes with tales of the past, from the rise of tycoons to the legacy of architectural triumphs, leaving travelers with a rich sense of the city’s heritage and an unforgettable experience of Chicago's Gold Coast.