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Lower West Side

Dive into the vibrant chaos of Chicago's Lower West Side! Colorful murals dance on brick walls, while tantalizing aromas waft from neighborhood taquerias. Explore quirky shops, groove to live music, and savor sensational street tacos. Don’t miss the scenic views along the Chicago River! This eclectic neighborhood is a true urban heartbeat bursting with culture and flavor!

From the Community

Recommendations

Culture4.8/5

National Museum of Mexican Art

This Chicago art museum brings Mexican art and Mexican American history into its galleries. A section focuses on political activism.

Transport4.7/5

18th

Landmark

Pilsen Art Community Murals

Landmark4.7/5

Cermak Road Bridge

Landmark3.5/5

Canal Street Bridge

This Chicago bridge crosses the South Branch of the Chicago River, with wooden planks underfoot on its sidewalks.

Landmark4.5/5

Harrison Park

Landmark4.5/5

Dvorak (Anton) Park

Landmark4.5/5

South Water Market Produce

Produce wholesaler in Chicago.

Landmark4.6/5

Monadnock Building

Culture4.9/5

Pilsen Arts & Community House

Chicago community art gallery and class space. Local artists show and sell work, with art displayed on both floors.

Eat$$4.9/5

Aloha Wagon

Aloha, beach lovers! Swing by Aloha Wagon for a taste of Hawaii in the heart of Chicago. Indulge in refreshing shaved ice treats and mouthwatering poke bowls. Located at 2023 S Western Ave, it's the perfect pitstop for a tropical escape in the Windy City. Mahalo!

Eat$$$4.7/5

The Duck Inn

Tucked away in vibrant Bridgeport, The Duck Inn is a cozy gem where craft cocktails and mouthwatering comfort food collide! Enjoy a delightful menu featuring duck specialties and hearty classics in a charming, laid-back atmosphere. With a lovely patio for sunny days and a warm interior, this spot is perfect for foodies and socialites alike. Quack on over! 🦆✨

Eat$$4.4/5

The Jibarito Stop

This Chicago sandwich shop serves Puerto Rican jibaritos, with fried plantains standing in for bread.

Eat

Alulu Brewery and Pub

Brewery and pub in Chicago's Pilsen neighborhood.

Eat$$$4.4/5

Pilsen Yards

Chicago Mexican restaurant with piña colada ceviche served with banana chips. Crunchy chips come with mole sauce, too.

Eat$$4.6/5

Carnitas Uruapan Restaurant

Eat$$$4.5/5

5 Rabanitos Restaurante & Taqueria

Eat$$4.3/5

Taqueria Los Comales Pilsen

Eat$$$4.5/5

Pochos

Eat$$$4.7/5

Parkview Restaurant Grill

Things To Do
Provided by

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

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became a global force in culture, commerce, and architecture. Our tour 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. While immersed in the places where it happened, Chicago's colorful stories will vividly spring to life. This walking tour aims to enhance your understanding of modern-day Chicago by a deep dive 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

Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At the museum, visit the Butterfly Haven and Birds of Chicago exhibit; admission is included. Walk through Victorian-style greenhouses with orchids and tropical palms, and see zoo habitats while hearing conservation stories from your guide.

$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

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

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

Chicago Haunted Interior Architecture Ghost Tour

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn from expert guides what makes Chicago one of the spookiest places in the world! Note, tour does not finish where it starts

$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

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

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.

$49.99

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

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!

$29.00

5/5

2 h 30 mins

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

$55.00

5/5

1 h 30 mins

Private Chicago Highlights Photography Session

Visitors to Chicago who want to capture fantastic vacation photos shouldn’t settle for smartphone selfies when you can book a professional photographer. With this photo shoot experience, simply meet your photographer-guide and enjoy a session with iconic Chicago landmarks as your backdrop. Photo shooting spots in Chicago: Millennium Park (including Cloud Gate) Willis Tower Skydeck Chicago Riverwalk Navy Pier North Avenue Beach The Magnificent Mile Wicker Park Lincoln Park Rooftop Chicago (extra charge may apply depending on the venue) Capture your most memorable moments during this private photo shoot. Return from your trip with beautiful, high-quality vacation photos — the best souvenir you can take home. PLEASE NOTE: This photo shoot package covers only one location from the list. Adding more locations will increase the package fee. The service fee mentioned is per person. This is not a group price. Please specify your preferred location from the list when making your booking.