Chicago City Tours

Earn OneKeyCash when you sign in and book an activity

Chicago City Tours

By Cavani Tours

Exceptional

Free cancellation available

See tickets

Features

Free cancellation available
8h
Mobile voucher
Instant confirmation
Selective hotel pickup
Multiple languages

Overview

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalised city tours offer a unique and unforgettable experience, customisable from 2 to 8 hours. From the iconic skyline to hidden gems off the beaten track, I’ll take you on a journey that captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!

Activity location

Millennium Park
- 201 East Randolph Street
- 60601-6530, Chicago, Illinois, United States

Meeting/Redemption Point

Millennium Park
- 201 East Randolph Street
- 60601-6530, Chicago, Illinois, United States

Check availability

Personalised 2-Hour Tour in Multilingual

8h
Opening hours: Mon 0:00-23:59
English

Duration: 2 hours
Personalised 2-Hour Tour: Our 2-hour tour is fully customisable. Choose the specific attractions or experiences you'd like to focus on, and we'll adjus
comfortable car
Pickup included

Travellers

Languages available

Price details

S$257.05 x 1 TravellerS$257.05

Total

Half day Tour (6H) in Multilingual

8h
Opening hours: Mon 0:00-23:59
English

Duration: 6 hours
Free snacks : enjoy the added perk of free snacks to make your experience even more enjoyable.
Half day Tour with Free Pics: Personalise your tour to suit your interests, and take home high-quality photos from your journey
comfortable car
Pickup included

Travellers

Languages available

Price details

S$579.97 x 1 TravellerS$579.97

Total

Day Tour (8H) in Multilingual

8h
Opening hours: Mon 0:00-23:59
English

40 minute break: Take a 40-minute break to relax and recharge with complimentary coffee and a selection of delightful sweets.
Personalised Photo Stops: Select unique and picturesque spots for photo opportunities, ensuring guests can take home beautiful memories.
comfy car
Duration: 8 hours
Free coffee and sweets: As you explore the city in style, enjoy gourmet coffee and delicious sweets at no extra cost.
All day Tour with Free Pics: Personalise your day tour by selecting your preferred route and stops from the itinerary. Your adventure, your way !
Pickup included

Travellers

Languages available

Price details

S$709.14 x 1 TravellerS$709.14

Total

What's included, what's not

Private transport
Bottled water
Snacks
Air-conditioned vehicle
Fuel surcharge
Parking Fees
Service charge

Know before you book

Infants and small children can ride in a pram or stroller
Service animals allowed
Public transport options are available nearby
Specialised infant seats are available
Suitable for all physical fitness levels

Activity itinerary

Millennium Park

Cloud Gate (The Bean): Visitors will see the iconic reflective sculpture, perfect for photos with the Chicago skyline. Crown Fountain: An interactive water feature with video projections and playful water sprays. Jay Pritzker Pavilion: A stunning outdoor amphitheatre, often hosting free concerts and events. Lurie Garden: A peaceful garden offering a scenic spot to relax amidst beautiful landscaping. Interactive Activities and Events: Temporary exhibits and cultural events to engage with during their visit. Biking and Walking: Nearby paths for biking or walking to explore the lakefront and nearby areas. Food and Shopping: A variety of food options and shops for a complete experience. Learn About the History: Opportunities to discover the park's history and cultural significance.

Chicago Riverwalk

Scenic Views: Enjoy stunning views of the Chicago River and iconic architecture. Walking and Biking: Ideal for strolling or biking along the water. Boating: Rent kayaks or take a river cruise to see the city from the water. Dining: Outdoor restaurants, cafes, and bars along the river. Public Art: Discover art installations and sculptures throughout the Riverwalk. Events: Live music, festivals, and entertainment depending on the season. Relaxation: Enjoy quiet spots to sit, relax, and take in the riverfront atmosphere.

Skydeck Chicago - Willis Tower

45m
Admission ticket not included

Panoramic Views: Stunning views from the 103rd floor of the Willis Tower. The Ledge: A glass-floored balcony extending outside for a thrilling view straight down. Interactive Exhibits: Learn about Chicago’s history and architecture. Souvenirs: Unique Chicago-themed gifts available at the gift shop. Photo Opportunities: Perfect spots for breathtaking photos of the city.

360 Chicago Observation Deck

45m
Admission ticket not included

Panoramic Views: Stunning 94th-floor views of Chicago and Lake Michigan. TILT Experience: Lean out over the city in a glass platform for a thrilling view. Interactive Displays: Learn about Chicago's history and landmarks. Observation Decks: Both indoor and outdoor areas for 360-degree views. Photo Opportunities: Great spots for capturing city views

Wrigley Field

20m
Admission ticket not included

Iconic Ballpark: Visit one of the oldest and most famous baseball stadiums in the US Chicago Cubs Experience: Watch a Chicago Cubs game or tour the stadium. Historic Atmosphere: Explore the rich history and tradition of Wrigley Field, including its ivy-covered outfield wall. Museum and Exhibits: Learn about the Cubs’ legacy through displays and memorabilia. Photo Opportunities: Capture iconic shots of the field, scoreboard, and vintage features.

Lincoln Park

Free Admission: Explore one of the oldest and most popular free zoos in the US Wildlife Exhibits: See a wide variety of animals, including lions, gorillas, and penguins. Historic Conservatory: Visit the Lincoln Park Conservatory with beautiful plant displays and seasonal flowers. Beautiful Gardens: Stroll through well-maintained gardens, perfect for relaxation and photography. Family-Friendly: Enjoy activities and exhibits suitable for all ages, making it a great spot for families. Lincoln Park Zoo and Conservatory offer a mix of wildlife encounters, lush gardens, and family-friendly experiences, all in a scenic, accessible setting.

Field Museum

40m
Admission ticket not included

World-Class Exhibits: Explore natural history exhibits, including fossils, ancient civilisations, and rare artefacts. Sue the T. rex: See the famous and largest T. rex skeleton ever discovered. Interactive Displays: Engage with hands-on exhibits and educational programmes. Cultural Exhibits: Learn about global cultures through diverse collections from around the world. Family-Friendly: Features activities and exhibits designed for all ages, making it great for families. The Field Museum offers a fascinating journey through science, history, and culture, with iconic exhibits like Sue the T. rex and engaging displays for all ages.

Skyspace At University Of Illinois At Chicago

Iconic Landmark: One of the largest fountains in the world, located in Grant Park. Impressive Water Show: Enjoy the spectacular water display, with water shooting up to 150 feet high, especially at night with colourful lighting. Historic Design: Built in 1927, it’s designed in the Beaux-Arts style and features four bronze sea horses. Scenic Views: Located near the lakefront, visitors can enjoy views of the fountain with the Chicago skyline in the background. Photo Opportunities: A popular spot for photography, especially during the fountain’s evening light shows. Clarence F. Buckingham Fountain offers a beautiful and historic landmark with stunning water shows, scenic views, and excellent photo opportunities.

Navy Pier

A bustling entertainment hub featuring a 15-story Ferris wheel, theatres, restaurants, and seasonal events, drawing approximately 8 million visitors annually

The Magnificent Mile

A premier shopping district along Michigan Avenue, lined with luxury boutiques, historic landmarks, and renowned eateries.

The Art Institute of Chicago

One of the oldest and largest art museums in the US, housing an extensive collection spanning centuries and cultures.

Museum Campus

A scenic lakefront area encompassing the Field Museum, Shedd Aquarium, and Adler Planetarium, offering insights into natural history, marine life, and astronomy.

Chicago Cultural Center

A stunning architectural gem hosting free art exhibitions, performances, and public events.

Jackson Park's Japanese Garden

A historic park on the South Side, home to the Museum of Science and Industry and beautiful lagoons.

North Avenue Beach

A popular spot for sunbathing, beach sports, and skyline views.

The Chicago Theatre

An iconic venue hosting concerts, plays, and special events in a historic setting.

Frank Lloyd Wright's Robie House

1m
Admission ticket not included

A Frank Lloyd Wright masterpiece located in Hyde Park, exemplifying Prairie School architecture.

Marquette Building

The Marquette Building, located at 140 S. Dearborn Street in Chicago’s Loop, is a celebrated example of early skyscraper design and a cornerstone of the city’s architectural heritage

The Rookery Building

The Rookery Building remains a cherished piece of Chicago's architectural heritage, reflecting the city's innovative spirit and historical depth.

Palmer House Hilton Historic Lobby

Originally opened in 1871 as a wedding gift from Potter Palmer to his bride Bertha Honoré, the hotel was rebuilt after the Great Chicago Fire and has since become a symbol of resilience and luxury. It holds the distinction of being North America's longest-operating hotel.

Union Station

Chicago Union Station stands as a remarkable blend of functionality and architectural beauty, reflecting the city's rich history and its pivotal role in America's transport network.

University of Chicago

a must-see destination for visitors to the city. Its beautiful campus blends Collegiate Gothic architecture with striking modern buildings, set among tree-lined quads and lush gardens. Highlights include the Rockefeller Memorial Chapel, the iconic Harper Library, and the Robie House—an architectural masterpiece by Frank Lloyd Wright.

Location

Activity location

Millennium Park
- 201 East Randolph Street
- 60601-6530, Chicago, Illinois, United States

Meeting/Redemption Point

Millennium Park
- 201 East Randolph Street
- 60601-6530, Chicago, Illinois, United States

Best Deals on Things to Do

Experience the wonders of the world up close with great deals on things to do near and far. Expedia offers one-of-a-kind activities that allow you to explore Chicago your way. Whether you love nature, culture, food or a bit of adventure, we have the perfect activity for you.

Top experiences in Chicago

With so many things to do in Chicago, planning the perfect day out may seem like a daunting task. Expedia is here to take the hassle out of finding the best attractions, tours and activities in Chicago. Families, couples and business travellers can all find the perfect activity in Chicago to create life-long memories with the help of Expedia.