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West Town

Dive into West Town, Chicago, where hip bars buzz, street art dazzles, and aroma-filled bakeries beckon! Stroll through vibrant neighborhoods lined with quirky boutiques and indulge in artisanal eats. Don’t miss the enchanting Humboldt Park—perfect for a picnic or a jog! This eclectic gem will captivate your senses and leave you craving more!

From the Community

Recommendations

Outdoor4.6/5

Wicker Park

Wicker Park is a vibrant urban oasis where art meets local flair! Just a stone's throw from the trendy boutiques and cafés, this pocket of greenery buzzes with energy. Stroll along the paths, admire the stunning sculptures, or kick back on the grass. Bring a picnic, or catch a live music show—there's always something fun happening at this Chicago gem!

Outdoor4.4/5

Pulaski (Casimir) Park

Culture4.8/5

Polish Museum of America

Culture4.7/5

Intuit Art Museum

Self Care4.5/5

AIRE Ancient Baths Chicago

Dive into relaxation at AIRE Ancient Baths Chicago, where history meets luxury! Nestled in a stunning, converted 19th-century factory, this spa transports you to the Mediterranean with thermal baths, massage treatments, and a candlelit atmosphere. Unplug, unwind, and pamper yourself with a unique spa experience that’s perfect for travelers seeking bliss in the Windy City!

Shop$$$4.6/5

Alcala's Western Wear

Landmark4.6/5

The Flatiron Arts Building

Outdoor4.8/5

The 606

Step onto The 606, a vibrant elevated trail in Chicago that blends urban charm with nature’s beauty. Packed with lush greenery and stunning artwork, this pedestrian haven allows you to bike, jog, or stroll through several diverse neighborhoods. Stop by the vibrant parks and cozy cafes along the way, and soak up the city's energetic atmosphere amidst the captivating skyline views.

Shop4.9/5

Paseo Boricua

Culture4.9/5

Church of Saint John Cantius

Landmark4.7/5

The Chicago Academy for the Arts

Culture4.8/5

Ukrainian Institute of Modern Art

The Ukrainian Institute of Modern Art showcases cutting-edge contemporary art while celebrating Ukrainian culture, making it a vibrant hub for creativity and community in Chicago's art scene.

Landmark4.8/5

North Avenue Beach Pier

Get ready to soak up the sun at North Avenue Beach Pier in Chicago! This iconic spot offers stunning views of Lake Michigan, perfect for relaxing or snapping envy-inducing Instagram pics. With sandy shores and plenty of water activities, it's the ultimate beach day destination. Don't forget your sunscreen and swimsuit!

Outdoor4.6/5

Burnham (Daniel) Park

Welcome to Burnham Park, Chicago's lakeside gem! Stretching along the breathtaking Lake Michigan shoreline, this park is perfect for picnics, biking, and leisurely strolls. With stunning views of the city skyline, lovely green spaces, and vibrant gardens, you’ll feel the city's heartbeat here. Don't forget your camera—this is a picture-perfect slice of Windy City joy!

Landmark4.7/5

Wicker Park Farmers Market

Landmark5/5

River West Lofts

Landmark2.3/5

Casa Aztlan

Culture4.6/5

Western Exhibitions

Culture4.8/5

Beta Project (Hubbard Street Murals)

Shop4.5/5

Una Mae's

Stays

Stay4.5/5

The Robey

The Robey in Chicago is a trendy hotel with a rooftop bar offering panoramic city views. The stylish rooms are adorned with vintage decor and modern amenities. Located in the vibrant Wicker Park neighborhood, guests can easily explore local boutiques, restaurants, and nightlife. Don't miss the chance to snap Instagram-worthy photos on the hotel's rooftop deck!

Things To Do
Provided by

5/5

2 h

Small-Group Sightseeing Boat Tour in Chicago

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!

$89.00

5/5

2 h

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

$566.82

5/5

1 h 45 mins

Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

$35.00

5/5

1 h 30 mins

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!

$90.00

5/5

1 h

Chicago Photo Walk to Bean and Landmarks

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building - all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery - you’ll have also visited many of the MUST-SEE places in downtown Chicago.

$169.00

5/5

2 h

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.

$162.50

5/5

2 h

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walking among gigantic towers of downtown, we will learn why and how Chicago became a global force in culture, commerce, and architecture. We will explore building interiors like the world's oldest skyscrapers, City Hall, the underground Pedway, and the old library. We will observe public art like the Picasso and the Bean. We will hear the stories of Chicago history while immersed in the places where it happened. This deep dive walking tour aims to enhance your understanding of modern-day Chicago by an exploration of its history. Your guide to the city is the friendly and well-informed Dave Lineal: local artist, culture vulture, and historian. Dave is tested and certified by the Chicago Tour-Guide Professionals Association. This is an outdoors / indoors all-weather walking tour with a duration of two hours. We will meet under the marquee at the Chicago Theater, 175 N. State Street.

$33.00

5/5

2 h

Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.

$315.00

5/5

2 h

Lincoln Park Zoo & Nature Museum Private Tour

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!

$274.98

5/5

1 h 45 mins

Intro to Chicago Architecture

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired European styles to bold American Art Deco and Modernist innovations to today’s Contemporary designs that continue to set the pace for world-leading architecture. As you journey through Chicago’s spectacular skyscraper canyons and stunning interiors, you’ll see how economics, technology, creativity, and gritty determination shaped Chicago’s ever-evolving skyline. Whether you’re a visitor or you’re a Chicagoan who has never explored the architectural masterpieces you see every day, join us today on this enlightening adventure.

$35.00

5/5

1 h 30 mins

Chicago River Cycleboat Cruise

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!

$65.00

5/5

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience

$180.00

5/5

3 h

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior (Ferris Bueller's Day Off), the Chicago Board of Trade exterior (The Dark Knight), Union Station's staircase (The Untouchables), and Millennium Park's Cloud Gate (Source Code). Enjoy a seamless and comfortable experience exploring these famous sites.

$315.00

5/5

3 h

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting monuments, you’ll discover the history, architecture, art, mob, cinema and secrets that made Chicago one of the most influential cities in the world. You’ll walk through iconic places and corners that most visitors never get to know: the Riverwalk, the fascinating Pedway, spectacular Tiffany domes, historic buildings, movie settings like The Intouchables, Batman and Transformers, plus the stories of Al Capone, Eliot Ness, the Dry Law and other characters that marked the city. Our 100% Spanish tours are guided by certified experts who turn each stop into an exciting story. You won’t just know Chicago; you’ll understand why millions of people fall in love and why this experience will be one of the best memories of your trip.

$45.00

5/5

4 h

Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city landmarks such as the Tribune Tower, Wrigley Building, and Buckingham Fountain. Led by a friendly local guide, this experience blends Chicago’s most famous eats, rich culture, and great photo ops — the perfect way to enjoy the best of the Windy City in one delicious day. Tour Ticket Includes: • 1 Portillo’s hot dog • 1 small Garrett’s Popcorn • 6" Al’s Italian Beef Sandwich • 1 slice of authentic Chicago deep dish pizza

$288.00

5/5

2 h

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.

$44.99

5/5

2 h

Chicago River Guided Ghost Tour

Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and the Eastland Disaster. You are welcome to bring your own beverages and food/snacks to fully enjoy your time on the water. Departing from the Chicago Riverwalk, this is a fun and engaging way to experience the spooky side of the city. This tour is typically smaller allowing for you to interact with the tour guide! Ask all the questions, we are ready! - 120-minute ghost tour on the Chicago River for up to 18 passengers - Fun bring-your-own beverage/snacks experience with a u-shaped bar and coolers - Learn about Chicago's haunted history and significant events - Departures from the Chicago Riverwalk—15-minute early arrival required to allow time for check in and depart on time.

$65.00

5/5

1 h 15 mins

The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin an immersive journey through the galleries. Together, we'll explore the museum's most celebrated highlights, featuring masterpieces by Monet, Picasso, Van Gogh, Dalí, Warhol, Hopper, and more. I'll share fascinating stories that bring the art and its creators to life, revealing the hidden meanings and personal histories behind. Along the way, I'll capture beautiful, candid photographs at the best photo spots. Using your phone or my iPhone 14 Pro, I'll guide you with simple posing tips and angles to ensure you receive stunning, professional-quality images perfect for memories or social media. Anyone looking for more than just a museum visit, you'll leave with gallery-worthy images plus knowledge that transforms how you experience art—an unforgettable blend of photography, storytelling, & culture. Looking forward to hosting you!

$101.00

5/5

2 h

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.

$44.99

5/5

2 h

Chicago Scavenger Hunt Adventure

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!