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Top things to do in Chicago

Chicago Architecture River Cruise Guided Tour
Cruises • Chicago

Chicago Architecture River Cruise Guided Tour

Book now for today
English guided
Free cancellation
Instant confirmation
★ 4.8 (121) • 8K+ booked
From € 33.65
360 Chicago Observation Deck Ticket
Observation decks • Chicago

360 Chicago Observation Deck Ticket

Book now for today
Free cancellation
Instant confirmation
★ 4.6 (60) • 10K+ booked
From € 26.35
Klook Pass Chicago
Attraction passes • Chicago

Klook Pass Chicago

Free cancellation
Instant confirmation
★ 4.8 (59) • 3K+ booked
€ 69.00
€ 86.75
Klook exclusive
Skydeck Chicago Entry Ticket
Observation decks • Chicago

Skydeck Chicago Entry Ticket

Book now for today
Instant confirmation
★ 4.8 (32) • 2K+ booked
€ 36.55
The Field Museum of Natural History Admission in Chicago
Museums • Chicago

The Field Museum of Natural History Admission in Chicago

Book now for today
Free cancellation
Instant confirmation
★ 4.7 (50) • 4K+ booked
From € 24.95
€ 24.99
Chicago CityPASS
Attraction passes • Chicago

Chicago CityPASS

Free cancellation
Instant confirmation
★ 4.8 (94) • 5K+ booked
€ 124.25
Quick Escape 45 Minute Chicago River Architectural Journey
Tours • Chicago

Quick Escape 45 Minute Chicago River Architectural Journey

Book now for today
English guided
Free cancellation
Instant confirmation
★ 5.0 (3) • 900+ booked
€ 24.15
The Art Institute of Chicago Ticket
Museums • Chicago

The Art Institute of Chicago Ticket

Book now for today
Instant confirmation
★ 4.8 (84) • 6K+ booked
€ 34.50
Flyover in Chicago Experience
Indoor games • Chicago

Flyover in Chicago Experience

Book now for today
English guided
Up to 3 hrs
Free cancellation
Instant confirmation
★ 5.0 (7) • 700+ booked
From € 24.10
Chicago Big Bus Hop-On Hop-Off Tours (Open-Top)
Tours • Chicago

Chicago Big Bus Hop-On Hop-Off Tours (Open-Top)

Book now for today
Free cancellation
Instant confirmation
★ 4.4 (35) • 1K+ booked
From € 42.29
First Lady Sightseeing River and Lake Cruise in Chicago
Cruises • Chicago

First Lady Sightseeing River and Lake Cruise in Chicago

Book now for today
English guided
Up to 3 hrs
Free cancellation
Instant confirmation
300+ booked
€ 39.69
Chicago Millennium Park Full-Day City Highlights Tour
Tours • From Chicago

Chicago Millennium Park Full-Day City Highlights Tour

Free cancellation
Instant confirmation
★ 3.0 (2) • 50+ booked
€ 74.75

Top attractions in Chicago

Tourist attraction
4.9/5(136K+ reviews)

Willis Tower

Welcome to the iconic Willis Tower, a marvel of modern architecture and a must-visit destination in Chicago. Originally known as the Sears Tower, this towering skyscraper stands as a testament to human ingenuity and ambition. As one of the tallest buildings in the Western Hemisphere, Willis Tower offers breathtaking views and unforgettable experiences, with panoramic vistas that stretch across Chicagoland and into four neighboring states. This architectural marvel not only redefines the workplace with its flexible office spaces but also offers a vibrant mix of retail and dining experiences. Whether you're a local or a tourist, the Skydeck at Willis Tower promises an adventure like no other, making it a beacon of innovation and culture and a must-visit destination for travelers from around the world.
Tourist attraction
4.9/5(137K+ reviews)

Chicago Riverwalk

Welcome to the enchanting Chicago Riverwalk, a vibrant urban oasis that captures the essence of the Windy City. Nestled along the south bank of the Chicago River, this award-winning, pedestrian-friendly promenade stretches 1.25 miles from Lake Michigan to Lake Street. The Riverwalk is more than just a scenic pathway; it's a lifestyle destination offering a delightful blend of culture, history, and modern attractions. Whether you're a local or a visitor, you'll find a unique experience here with its stunning natural beauty, diverse dining options, and engaging activities. From cultural landmarks to modern amenities, the Chicago Riverwalk is a must-visit destination for anyone seeking to explore the heart of Chicago.
Tourist attraction
4.9/5(137K+ reviews)

DuSable Bridge

Discover the DuSable Bridge, an iconic marvel of engineering nestled in the heart of Chicago. This architectural gem spans the Chicago River, seamlessly connecting the vibrant neighborhoods of the Near North Side and the Loop. As a hidden gem, it offers breathtaking views and a journey through time, standing as a testament to the city's rich history and architectural prowess. The DuSable Bridge not only serves as a vital transportation link but also embodies Chicago's ambition and cultural homage to European elegance. It connects the bustling business district with a Parisian-inspired boulevard, serving as a gateway to the city's rich past and vibrant present. Whether you're a history buff, architecture enthusiast, or simply a curious traveler, the DuSable Bridge promises an unforgettable experience in the Windy City.
Tourist attraction
4.9/5(146K+ reviews)

Navy Pier

Located in Chicago, Illinois, Navy Pier has been around since 1916 and is a must-visit spot in the city. You can enjoy fireworks, music, theater, and cruises in the summer. Even in the fall and winter, Navy Pier is bustling with cool events for everyone to enjoy. With over nine million visitors every year, it's packed with restaurants, shops, shows in the festival hall, family pavilion, and more to entertain you. Get on the giant Ferris wheel, have a blast at the Chicago Children’s Museum, visit the Peoples Energy Welcome Pavilion, catch a free concert, or go on an art hunt, all while taking in awesome views of Lake Michigan and the city skyline. Thrill-seekers will dig the speedboat tours, but a sightseeing cruise with dining cruise boats will do the trick if you prefer a more relaxed vibe. If you're driving, know that parking can be pricey, so consider using public transportation. And if you hop on a Chicago River cruise, you'll cruise by this municipal pier. Don’t miss out on this fantastic spot on Grand Ave!
Museum
4.9/5(143K+ reviews)

The Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and biggest art museums in the U.S., and you won't want to miss it if you love art. Located on Michigan Avenue, Illinois, Chicago, it has the biggest collection of Impressionist and Post-Impressionist art in the world, next to the Louvre. They have over 300,000 pieces of art, including some of the most famous works ever. The museum also has lots of special exhibits and fun events. You'll get to see all kinds of artwork, from paintings and sculptures to prints and drawings that go way back in time. You'll see stuff like ancient pottery, Greek art, and modern pieces like Picasso’s The Guitarist and Hopper’s Nighthawks. Plus, you get to see famous art like Gustave Caillebotte’s Paris Street; Rainy Day, Georges Seurat’s A Sunday on La Grande Jatte — 1884, Grant Wood’s American Gothic, and Vincent van Gogh’s The Bedroom. These are just some of the awesome pieces you'll get to check out at the Art Institute of Chicago.
Scenic spot
4.9/5(146K+ reviews)

Cloud Gate

Discover the mesmerizing allure of Cloud Gate, affectionately known as 'The Bean', a captivating public sculpture nestled in the heart of Chicago's Millennium Park. This iconic masterpiece by artist Anish Kapoor draws visitors from around the globe with its unique reflective surface and stunning design. As a must-see marvel, it offers a unique blend of art and architecture that mirrors the city's vibrant skyline and lush surroundings. Whether you're an art enthusiast or a curious traveler, 'The Bean' promises an unforgettable experience, capturing the essence of Chicago's urban charm and artistic brilliance.
4.9/5(136K+ reviews)

Skydeck Chicago

Located on top of the iconic Willis Tower, Skydeck Chicago is a must-visit attraction in the city. Get set for amazing views of downtown Chicago and up to four states from the highest observation deck in the United States. See amazing views from The Ledge, five glass floor balconies extending 4.3 feet from the Willis Tower’s 103rd floor. Skydeck Chicago has recently undergone a makeover, offering a new museum-like interactive experience that showcases Chicago's unique history and neighborhoods. Don't forget to hop on the multimedia elevator ride, one of the fastest in the world, which points out interesting landmarks as you go up. When you reach the 103rd floor of the Willis Tower, get ready for unbeatable views and top-notch exhibits that will make your visit truly memorable. Book your ticket now for an unforgettable adventure in the heart of Chicago!
Botanical garden
4.9/5(104K+ reviews)

Lincoln Park Conservatory

Nestled in the heart of Chicago, the Lincoln Park Conservatory is a botanical haven that offers a serene escape from the bustling city life. Step into a world of beauty and tranquility at this Victorian Era glass house, built between 1890 and 1895, where the air is rich with oxygen and the scent of tropical flowers fills the atmosphere. Discover this lush oasis, a captivating destination that invites visitors to explore its vibrant plant collections and historic architecture. As part of Chicago's largest and most vibrant green space, the conservatory offers a rich tapestry of nature, culture, and recreation, making it a must-visit destination for nature enthusiasts and history buffs alike.
Museum
4.9/5(135K+ reviews)

Museum Of Contemporary Art Chicago

Discover the vibrant world of contemporary art at the Museum of Contemporary Art Chicago, a cultural gem nestled in the heart of the Windy City. This dynamic hub for art enthusiasts and cultural explorers offers a captivating journey through modern creativity. With its innovative exhibitions and thought-provoking performances, the museum challenges and inspires visitors from around the globe. Whether you're an art aficionado or a casual visitor, the Museum of Contemporary Art Chicago promises an ever-evolving array of exhibitions and programs that push the boundaries of artistic expression. Located in the heart of Chicago, this museum is a must-visit destination for anyone looking to explore the cutting edge of contemporary art.

Hotels in Chicago

Warwick Allerton - Chicago
Hotels • Chicago

Warwick Allerton - Chicago

Instant confirmation
★ 4.3 (2,993)
From € 124.49
Congress Plaza Hotel
Hotels • Chicago

Congress Plaza Hotel

Instant confirmation
★ 4.0 (10,190)
From € 113.81
Freehand Chicago
Hotels • Chicago

Freehand Chicago

Instant confirmation
★ 3.9 (3,255)
From € 99.16
River Hotel
Hotels • Chicago

River Hotel

Instant confirmation
★ 4.4 (5,390)
From € 132.10
The Whitehall Hotel, BW Premier Collection
Hotels • Chicago

The Whitehall Hotel, BW Premier Collection

Instant confirmation
★ 4.2 (3,943)
From € 149.30
L7 Chicago by LOTTE
Hotels • Chicago

L7 Chicago by LOTTE

Instant confirmation
★ 4.8 (4,489)
From € 176.55
Hilton Chicago O'Hare Airport
Hotels • Chicago

Hilton Chicago O'Hare Airport

Instant confirmation
★ 4.2 (2,363)
From € 210.25
The Chicago Hotel Collection - Magnificent Mile
Hotels • Chicago

The Chicago Hotel Collection - Magnificent Mile

Instant confirmation
★ 3.9 (1,878)
From € 156.65
Holiday Inn & Suites Chicago - Downtown by IHG
Hotels • Chicago

Holiday Inn & Suites Chicago - Downtown by IHG

Instant confirmation
★ 4.3 (1,125)
From € 126.15
Hyatt Regency McCormick Place Chicago
Hotels • Chicago

Hyatt Regency McCormick Place Chicago

Instant confirmation
★ 4.6 (1,233)
From € 194.00
Hotel Chicago West Loop, SureStay Collection by Best Western
Hotels • Chicago

Hotel Chicago West Loop, SureStay Collection by Best Western

Instant confirmation
★ 4.1 (1,158)
From € 173.59
Hilton Chicago
Hotels • Chicago

Hilton Chicago

Instant confirmation
★ 4.3 (3,018)
From € 170.16

Reviews of Chicago activities

CHU **********
2026-05-22 09:18:47
Fantastic 5.0
Booking the Chicago Architecture Boat Tour on Klook was absolutely the best decision of this trip! The 90-minute cruise sailed along the three branches of the Chicago River, with stunning skyscrapers lining both banks. Our guide, Liam, was incredibly professional and humorous, sharing fascinating stories from Chicago's rebirth after the Great Fire of 1871 to the art of modern steel structures and glass curtain walls (like Marina City and Willis Tower). Even someone with no architectural background could thoroughly enjoy it. The views from the boat were excellent; it was convenient to either enjoy the breeze and take photos on the open-air upper deck or relax in the air-conditioned lower cabin and grab a drink. I highly recommend this classic tour to all first-time visitors to Chicago – it's not to be missed! (It would be even better if multilingual commentary were available in the future.)
Klook User
2026-03-10 03:10:25
Fantastic 5.0
Very easy of booking with Klook, straight forward and fast. The 360 Chicago Observation Deck was amazing. Up there just take your time and enjoy the view.
Klook User
2026-04-09 20:19:32
Fantastic 5.0
I found this to be the better option than other citypasses since it fit the attractions I wanted to go to. Just be sure of the dates you're going on because once you do that the ticket is nonrefundable and unchangeable.
erickson ****
2026-05-17 16:07:15
Fantastic 5.0
Fantastic museum with amazing exhibits and rich history. Seeing Sue the T. rex was incredible, and the museum was very well maintained and educational. Great experience for all ages!
Joel *******
2026-06-01 12:00:34
Fantastic 5.0
The 45 min river cruise is a definite must see on your Chicago itinerary. A guide will give a highlight for each major building.
Mariel ******
2026-06-06 06:11:55
Fantastic 5.0
I bought tickets for 8PM and it was perfect because it was still slightly bright outside and we could see watch the sunset. It was pretty organized and not too crowded on a Thursday night.
erickson ****
2026-05-17 16:08:41
Fantastic 5.0
One of the best ways to experience Chicago! The tour was informative, relaxing, and the city skyline views were stunning. Learned so much about Chicago’s architecture while enjoying the river cruise.
JS **
2026-05-05 21:39:40
Fantastic 5.0
it's a fun experience to see the city. very immersive fly through with video and music although it would be good to give some more info during the flyover.
CHEN ******
2026-03-31 02:40:58
Fantastic 5.0
The Chicago architectural aesthetics tour led by Peter was an incredibly wonderful experience, truly deserving of high praise! The itinerary covered the geography, history, and architectural art of Chicago, USA, along with local cuisine. Iconic landmarks such as the Chicago Tribune Tower, Wrigley Building, DuSable Bridge, Trump Tower, and Marina City were all connected, from historical to modern architecture, providing a more comprehensive understanding of Chicago. The tour also included visits to McDonald's headquarters and the United Center, showcasing the integration of corporate and urban development. The breathtaking 360-degree observation deck offering panoramic city skyline views was truly stunning. Furthermore, the Art Institute of Chicago extended the journey beyond architecture to the aesthetics of art and public spaces. Peter's explanations were insightful and vivid, making it easy to understand the stories behind each attraction. It was a highly rewarding and recommended cultural tour!

Chicago at a glance

When is the busiest time for Chicago activities?

Book earlier for peak months

Busier than usual Quieter than usual
+200%
+100%
Typical
-100%
0%
Jan
-91% Quietest
Feb
-65%
Mar
-48%
Apr
+39%
May
+17%
Jun
Busiest +104%
Jul
-30%
Aug
-61%
Sep
+31%
Oct
Busiest +104%
Nov
-44%
Dec

Demand for Chicago peaks in July and November (about +104% vs a typical month) while February is much quieter (about 91% below a typical month); travellers from the Philippines should book early for July and November peaks to secure availability and avoid crowds. Based on Klook historical booking data.

When is Chicago cheapest?

Find months that fit your budget. Prices in USD.

$500
$400
$300
$200
$100
$0
Avg $98 Priciest $465 Cheapest $28
Jul Aug Sep Oct Nov Dec Feb Mar Apr May Jun

Activities in Chicago are typically cheapest in March (around USD 28), roughly 94% below the priciest month in February; this cheaper March aligns with the quiet February demand window, so expect better value and availability in that period. Based on Klook booking data, July 2025 – June 2026.

How far ahead should you book?

Plan ahead so you don’t miss out

0 daysLast-minute
1 daysTypical
8 daysEarly

Most travellers book about 1 day ahead, with the early-booking side at about 8 days, so travellers from the Philippines have flexibility but should book earlier during the July and November peaks named on the demand chart. Based on Klook booking data, February 2026 – July 2026.

Quick facts about Chicago

General info
  • Time zone

    No time difference

  • Currency

    1EUR = 1.16USD

  • Official languages

  • Best time to visit

    Chicago Blues Festival

What to know before visiting Chicago

Chicago at a glance — museums, observation decks and cruises

Chicago’s top bookings on Klook cluster around observation decks, attraction passes, museums and cruises, so the city suits travellers who enjoy skyline views, cultural stops and lakefront experiences. Demand peaks strongly in July and November, with much lighter interest in late winter and early spring.

When to visit — peak months and price rhythms

Klook booking data show the busiest months are July and November, while demand is lowest in February. Prices move unevenly through the year: they climb into late autumn and winter and hit unusually high levels in February, but Klook data also show March as typically the cheapest month for activities. If you want lower prices and smaller crowds, plan for March or other shoulder months when demand is softer; for lively, peak-season atmosphere, aim for July or November. Note that prices and demand don’t always match perfectly — the most expensive month by Klook activity prices is February even though February is a trough for bookings.

Tips for travellers from the Philippines

Most visitors from the Philippines on Klook tend to book very close to travel dates, typically around a day ahead, so a flexible or spontaneous trip works well. If you’re travelling in the busy months named above, consider locking popular activities in earlier (around a week ahead) to secure spots. Use Klook to compare passes, observation-deck tickets and museum options so you can build an efficient itinerary quickly.

FAQs about Chicago

When is the best time to visit Chicago?

When is the cheapest time to visit Chicago?

How far ahead should I book Chicago activities if I'm travelling from the Philippines?

How much do activities in Chicago typically cost?