26 Popular Places to Visit and Top Things to Do in Chicago, IL

June 4, 2022 Mustafa Natalwala 2922 Views

Chicago is a major city in the state of Illinois in the United States of America. Also known as the Windy City, Chicago sits on the shore of Lake Michigan where it is met by the Mississippi River. There are a lot of fun things to do in Chicago. It is a vibrant city with a lot of variety. Almost all types of people would find something that interests them. The city has a unique history of its own and is deeply ingrained in the history of the USA as well. Some of the best places to visit in Chicago are historical sites concerning American Revolution, Celebrity House Museums, History Museums, Black History Historical Sites, and City’s History Museum. There are several interesting walking and bicycle tours concerning several aspects of Chicago sightseeing. Some of the popular ones are history tours, gangster tours, haunted places tours, street food tours, architecture tours, and so on.

It is a city of skyscrapers so the city skyline is among the most wonderful things to see in Chicago. There are several buildings that have observation decks for this purpose. You can also take boat cruise tours in Lake Michigan or in the Mississippi River to enjoy the architecture of the city. You can also get sailing and kayaking tours. The lake is the epicenter for the majority of fun outdoor activities in Chicago. It is a place where you can truly experience the leisurely side of Chicago travel. There are walking and cycling trails, beach sports, swimming areas, beach-side bars, street food joints, volleyball courts, and so on. Another one of Chicago’s tourist attractions famous for entertainment and leisure is Navy Pier.

As you explore the city, you will get to understand its culture and spirit. There are fun places to go in Chicago concerning stand-up comedy, food, jazz, performance art, visual art, and more. The city is also known for its adoration of sports teams. So if you want to get in touch with the city’s spirit you should check out a game at any one of the stadiums. They are Chicago tourist spots in their own right. This is also true for some of the food joints. The city is famous for its puff pizza and its own rendition of hot dogs. There are also organized tours to help you cover as many joints as you can when you visit Chicago.

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Table of Contents

Top 26 Tourist Places to Visit in Chicago in 5 Days (Trip Itinerary)

Day 1

1. Alder Planetarium

This was the very first planetarium in the United States of America and now also serves as a National Historic Museum. It is one of the best places to visit in Chicago if you are interested in cosmology and astronomy. You will need about an hour to tour this planetarium.

2. John G Shedd Aquarium

The aquarium was commissioned by John G Shedd as a way of giving back to the city. It is not only popular as an aquarium, but also for its architecture which is inspired by Greek and Roman temples. This place offers a lot of fun things to do in Chicago for family tourists. There are 1500 species of animals in the aquarium and it also puts up a variety of shows and activities with animals. You can easily spend a couple of hours at this place.

I suggest you should book your ticket for John G Shedd Aquarium in advance.

3. Millenium Park

The park was originally intended to celebrate the 2000 millennium. It is spread over 99,000 square meters and there is a lot of stuff to do in Chicago exclusive to this park. You will see public art displays, entertainment venues, sports facilities, leisure activities, and recreational areas in this park. It will take you at least an hour to explore Millennium Park.

4. Chicago Children’s Museum

This museum showcases history through interactive exhibits, games, and activities. It is a great place for children to learn things and to keep them entertainingly engaged. Though if you are not with children, you can skip this place. This museum requires at least 2 hours’ time.

5. Navy Pier

The pier was originally designed in 1916 and was further developed in 2016 to celebrate its anniversary. The pier offers a variety of entertainment activities to do in Chicago. It has themed restaurants, amusement venues, bars, clubs, performances, and theatres. You would have an hour or two to explore this place when you visit Chicago.

I suggest you must book your ticket for Navy Pier with Centennial Wheel in advance.

6. Driehaus Museum

This museum celebrates the “Gilded Age of America”. The exhibits include decorative art pieces from the 19th and 20th centuries. The building itself is quite renowned for its art nouveau design and architectural elements. Some of the most fascinating things to see in Chicago can be found in this museum. You will need an hour to tour Driehaus Museum.

7. 360 Chicago

This observation deck is situated in the John Hancock Center and sits 1000 feet above the ground. It is one of the best Chicago tourist attractions to visit for a bird’s eye view of the windy city and its dominating skyline of skyscrapers. It is also one of the best things to do in Chicago at night as the city becomes a kaleidoscope of lights of various colors with a few patches of darkness. You will need 30 to 45 minutes for this experience.

I suggest you must buy the Skip-the-Line Ticket of 360 Chicago Observation Deck in advance.

Day 2

1. Lake Michigan / Lakefront Trail

Lake Michigan falls on the east side of Chicago. The 29 km of Lakefront trail is popular among locals and tourists alike for several outdoor activities in Chicago. The trail runs along a beautiful beach and has facilities for bicycle rides, football, volleyball, jogging, tennis, picnics, and so on. You can easily spend a couple of hours enjoying the lakeside.

There are different activities that you can do at Lake Michigan. Here below I have suggested some of the activities that you should do at Lake Michigan or Lakefront Trail

2. Art Institute of Chicago

The museum in this institute has one the best art collection in the country. The exhibits include artworks, artifacts, decorative art pieces, textiles, architectural elements, and photographs from Americas, Europe and Asia. It is one of the most fascinating Chicago attractions. You will come across arts works of renowned artists such as Van Gogh, Monet, Renoir, Picasso, Cezanne, Magritte and Matisse. You will need about 2 hours to explore this place during Chicago travel.

I suggest you should book guided tour of Art Institute of Chicago with Skip the line option.

3. Fine Arts Building

This 10 storey building was first designed to be an art institute and later became a studio. It is well known to have hosted several well known artists like Frank Loyd Wright, William Denslow, Harriet Monroe and more. It is also renowned for its interior elements including decorative arts, furniture, interior designs, paintings and murals. You will need about 30 to 45 minutes to explore this place.

4. Rookery Building

This iconic landmark was designed by Daniel Burnham and John Wellborn Root. It was one of the earliest high rise buildings in the city and is still renowned for its intricate architectural and design features. It is one of the most beautiful places to see in Chicago and will require an hour’s time to explore.

5. Chicago Fed Money Museum

This museum will give you an insight into the federal reserve system and how money functions in the American economy. It is one of Chicago tourist spots with free guided tour which takes place on Mondays and Fridays. The tour takes 45 to 50 minutes.

6. Willis Tower Skydeck

This observation deck stands 442 meters above the ground and is situated on the 103rd floor of the Willis Tower. You get a nice 360 degree view of the city. The observation deck also has a balcony with glass floors. It is one of the most fun places to go in Chicago as you sometimes see people’s different reactions to the glass floors. You will need 30 to 45 minutes for this experience.

I suggest you must get Ticket of Willis Tower Skydeck with Skip the line option in advance.

Day 3

1. Chicago History Museum

This museum tells the story of Chicago. The exhibits include artifacts, documents and photographs. The museum also focuses on the evolution of the city’s culture in terms of trends, food, fashion, music and more. It is definitely one of the best places to visit in Chicago to understand the city and its people. You will need about 2 hours to tour this museum.

You can book your ticket of Chicago History Museum in advance.

2. Lincoln Park Zoo

The Zoo has animals brought in from around the world. Some of the highlights include lions, sea lions, polar bear, swans, zebra and penguins. It is one of the top things to do in Chicago for family tourists. Beside animals, the zoo is also has wonderful statues, relief artworks, entertainment activities and mini-train rides. You will need at least 2 hours at this zoo during Chicago travel.

3. Lincoln Park Conservatory

The conservatory dates back to 1890 and has several elements of Victorian architecture of glasshouses. The four displays of the conservatory has a variety of plants and also a few exotic plants. The glasshouses are among the most magnificent things to see in Chicago. You will need an hour to tour the conservatory.

4. Peggy Notebaert Nature Museum

This natural history museum has indoor and outdoor exhibits focusing on the evolution of life on earth. It is quite popular among Chicago tourist attractions for families. If you have interest in plants, animals and birds, especially the lost ones; you will truly enjoy this museum. It will take you about 2 hours to tour it.

Day 4

1. International Museum of Surgical Science

The museum showcases evolution of surgical science over the centuries. The museum has some unusual artifacts, sculptures, paintings and more to highlight milestones in the field. It is one of the most interesting Chicago attractions and will require an hour to explore.

You can book your ticket of International Museum of Surgical Science in advance.

2. Museum of Contemporary Art (MCA Chicago)

The museum exhibits artworks created after 1945. The exhibits include paintings, art installations, sculptures, video art, photographs, performance art, pop art and more. The museum is an integral part of Chicago sightseeing and will require about 2 hours of time to tour.

I suggest you should get your ticket of Museum of Contemporary Art in advance.

3. McCormick Bridgehouse & River Museum

This museum focuses on the relationship of the city, the rivers and the movable bridges. It is not a very well known Chicago tourist spots but gives quite an interesting insight into the city’s history. You will need 30 to 45 minutes to tour this museum.

4. Field Museum of Natural History

This natural history museum has a lot to see and enjoy. Aside from variety of artifacts, this museum has wonderful scale models and 3D movies. It is one of the most fun places to go in Chicago. You will need at least 2 hours to tour this museum.

You should book your ticket of the Field Museum of Natural History in advance.

Day 5

1. Museum of Science and Industry

This is the largest museum in the western hemisphere. The museum focuses on science, technology and industrialization. It not only exhibits world of the past but also showcases upcoming technologies. The museum is also popular for recreational and hands-on activities to do in Chicago. You will need 2 hours to tour this museum.

2. Frederick C. Robie House

This house is located on the University of Chicago’s campus and was designed by Frank Loyd Wright. It is included among top places to see in Chicago as a prime example of Wright’s Prairie style of architecture. It will take you 30 to 45 minutes to explore this place when you visit Chicago.

Get your ticket of Frederick C. Robie House in advance.

3. Oriental Institute Museum

This museum showcases artifacts concerning history and culture of the Near East. The exhibits hail from civilizations of Egypt, Mesopotamia, Syria, Iran, Israel and so on. The museum will require at least 2 hours of time to explore.

4. DuSable Museum of African American History

This is oldest as well as the largest museum dedicated to the history and culture of the African Americans in the USA. The museum has several different types of exhibits including artifacts, documents, photographs, art installations, paintings, sculptures, video footages, portraits and more. You will need about 2 hours to tour this museum.

5. Chicago Botanic Garden

There are 25 display gardens and 4 recreated natural habitats on these premises. You will see a variety of flora hailing from different parts of the world in these gardens. It will take you at least an hour to explore these gardens.

If you are looking for more cool things to do in Chicago, check out the sections below. We have put together an exhaustive list of places to explore and fun stuff to do in Chicago.

Things to do in Chicago

Monuments, Museums & Historical Places to Visit in Chicago

The Art Institute of Chicago
Field Museum
Museum of Science and Industry
Cloud Gate Sculpture
Museum of Contemporary
Adler Planetarium
Chicago History Museum
Chicago Culture Center
Frederick C. Robie House
The Chicago Theatre
Chicago Children’s Museum
Frank Lloyd Wright Home & Studio
DuSable Museum of African American History
Oriental Institute Museum
Peggy Notebaert Nature Museum
Museum of Contemporary Photography
National Museum of Mexican Art
Smart Museum of Art
Unity Temple
Baha’i House of Worship
The Richard H. Driehaus Museum
Chicago Water Tower
City Gallery
American Writers Museum
Jane Adams Hull House Museum
International Museum of Surgical Science
Newberry Library
Museum Campus
Thomas Hughes Children’s Library
Pullman National Monument
Glessner House Museum
Block Museum of Art
The Renaissance Society
Illinois Holocaust Museum and Education
Chicago Symphony Orchestra
Intuit: The Center for the Intuitive and Outsider Art
S. R. Crown Hall
Hyde Park Art Center
DePaul Art Museum
Pritzker Military Museum & Library
Graceland Cemetery
WNDR Museum
Kavi Gupta Gallery
Swedish American Museum
The Arts Club of Chicago
Henry B. Clarke House
Calder’s Flamingo Sculpture
Loyola University Museum of Art
Woman Made Gallery
Medieval Torture Museum
Joliet Iron Works Historic Site

Nature & Wildlife Tourist Spots in Chicago

Northerly Island Park
Waterfall Glenn
Des Plaines River
Matthiessen State Park
Busse Woods
Kankakee River State Park
Glacial Park Conservation Area
Edward L. Ryerson Conservation Area
Rock Cut State Park
Moraine Hills State Park
Castle Rock State Park
The Morton Arboretum

Entertainment & Leisure Tourist Spots in Chicago

Navy Pier
Shedd Aquarium
Millenium Park
Lincoln Park Zoo
Skydeck Chicago
Grant Park
Garfield Park Conservatory
Brookfield Zoo
360 Chicago
Maggie Daley Park Ice Skating Ribbon
Lakefront Trail
Chicago Architecture Center
Soldier Field
The 606
Lincoln Park Conservatory
Jay Pritzker Pavilion
Jackson Park
Lurie Garden
Lincoln Park
Alfred Caldwell Lily Pool
Oz Park
Centennial Wheel
Humboldt Park
Chicago Zoological Society
Time Out Market
Legoland Discovery Center

Shopping in Chicago

The Merchandise Mart
State Street
Woodfield Mall
Lincoln Square
The Magnificent Mile
900 North Michigan Shops
Andersonville
Belmont Avenue
Streeterville
Oak Street
Jeweller’s Row
Lincoln Park
Roscoe Village
Maxwell Street Market
Water Tower Place
Gurnee Mills
Fashion Outlets of Chicago
Bucktown and Wicker Park
River North
Armitage Venue

Beaches & Islands in Chicago

Lake Michigan Beach
Lane Beach
North Avenue Beach
Oak Street Beach
Montrose Beach
Gold Coast Beach

Offbeat Places, Tours, & Adventure Activities to Do in Chicago

River Cruise
Lake Cruise
Motorboat Tour
Sailing
Yacht Tour
Gangsters / Mafia Tour
Hiking
Camping
Kayaking
Haunted Places Tour
Architecture Tour
Ice Skating
Bicycle Tour
Helicopter Tour
Nature Walk
Skydiving
Indoor Skydiving

Sightseeing in Chicago

Willis Tower
Buckingham Fountain
Wrigley Field
875 North Michigan Avenue
Chicago Riverwalk
Tribune Tower
Crown Fountain
Rookery Building
The Wrigley Building
Chicago Board of Trade Building
DuSable Bridge
Promontory Point
Richard J Daley Center
Marina City Goldberg Complex
Sullivan Center
The Chicago Picasso Sculpture
Monadnock Building
McCormick Tribune Plaza
Northerly Island
North Clark Street
Reliance Building

Food, Dining, Restaurants, & Street Food in Chicago

Lou Malnati’s Pizzeria
Superdawg Drive In
Pequod’s Pizza
Little Italy
Piece Brewery
Portillo’s Hot Dogs
Spacca Napoli Pizzeria
Longman & Eagle
Shokolad Pastry & Cafe
Fatso’s Last Stand
Cindy’s Rooftop
Wolfy’s
Daisies
Chicago’s Dog House
Fontano’s Subs
The Duck Inn
Mi Tocaya Antojeria
Lola’s Coney Island
Cityscape Bar
Redhot Ranch
Giant
The Rosebud
Paulie Gee’s
Z Bar
Owen & Engine
Lula Cafe
Kyoten

Where to Stay in Chicago?

Here we have listed Top Rated Luxurious, Mid-Range and Budget Hotels in Chicago. You can check below listed hotels for your perfect stay in Chicago.

Luxurious Hotels

Mid-Range Hotels

Budget Hotels

Custom Tours Package in Chicago

How to Reach Chicago?

By Air

The city of Chicago is served by two airports: O’Hare International Airport and Midway Airport. You will get cabs and buses to reach places to visit in Chicago. But the cab fares can be expensive, especially during high traffic hours. You can also choose the metro to get around the city. Both airports are connected by CTA trains. O’Hare is connected through Blue Line and Midway through Orange Line.

The Midway Airport majorly receives domestic flights from cities in the USA such as Orlando, Los Angeles, Las Vegas, Phoenix, New York, Atlanta, Denver, Dallas, Tampa, Houston, Boston, Detroit, Philadelphia, Charleston, New Orleans, Nashville, San Diego, San Francisco and many more. It also receives International Flights from cities in Canada, Jamaica, Dominican Republic, and Mexico. You can reach Chicago through Midway airport from Toronto, Cancun, Morelia, Montego Bay, Punta Cana, and so on.

The O’Hare International Airport receives flights from cities in the USA. It is the premier airport for international flights. You can get direct flights to visit Chicago from major cities in Europe, South America, North America, and Asia such as Dublin, Mexico City, Montreal, Paris, Delhi, Auckland, Tokyo, Vienna, London, Hong Kong, Shanghai, Panama City, Dubai, Abu Dhabi, Taipei, Helsinki, Beijing, Madrid, Amsterdam, Reykjavik, Seoul, Krakow, Warsaw, Munich, Frankfurt, Doha, Copenhagen, Stockholm, Baltimore, Zurich, Lisbon, Istanbul and many more.

By Road

You can direct buses to reach Chicago from several cities in America such as Atlanta, Cincinnati, Cleveland, Columbia, Dallas, Detroit, Iowa City, Kansas City, Louisville, Madison, Memphis, New York, Nashville, Omaha, and many more. You also get buses from Mexico and Canada.

Chicago sits on several Amtrak routes including Hiawatha, Illinois Service, Lake Shore Limited, Michigan Services, Southwest Chief, Texas Eagle, Capitol Limited, Cardinal, and City of New Orleans. These routes connect Chicago to various cities in the USA such as Milwaukee, St Louis, Omaha, Denver, Salt Lake City, San Francisco, Washington DC, Pittsburg, Cleveland, New York, Charlottesville, Seattle, Boston, Detroit, and many more.

If you are planning for Chicago travel by road, you should head for routes I-55, I-90, I-94, I-88, I-355, or I-294.

By Water

There are a few boat cruises and tours of Lake Michigan which connect with Chicago. Although these are only used for sightseeing. The cruises are among the coolest things to do in Chicago but they are not a travel option.

Image Reference

Adler Planetarium – Terence Faircloth / Flickr
John G. Shedd Aquarium – Tony Hisgett / Flickr
Millennium Park – Kristina D.C. Hoeppner / Flickr
Chicago Children’s Museum – Lawrence G. Miller / Flickr
Navy Pier – Marit & Toomas Hinnosaar / Flickr
Driehaus Museum – Joyofmuseums / Wikimedia Commons
360 Chicago – Olivier Bruchez / Flickr
Lakefront Trail – The West End / Flickr
Art Institute of Chicago – ajay_suresh / Flickr
Fine Arts Building – Eric Allix Rogers / Flickr
Rookery Building – A Ryan / Flickr
Chicago Fed Money Museum – Steve Rhodes / Flickr
Willis Tower Skydeck – Bari D / Flickr
Chicago History Museum – Alanscottwalker / Wikimedia Commons
Lincoln Park Zoo – opacity / Flickr
Lincoln Park Conservatory – esimpraim / Flickr
Peggy Notebaert Nature Museum – Carolien Coenen / Flickr
International Museum of Surgical Science – darius norvilas / Flickr
Museum of Contemporary Art (MCA Chicago) – hibino / Flickr
McCormick Bridgehouse & River Museum – Jeremy Atherton / Wikimedia Commons
Field Museum of Natural History – Heather Paul / Flickr
Museum of Science and Industry – Day_Photo / PixaBay
Frederick C. Robie House – Teemu008 / Flickr
Oriental Institute Museum – Aaron Volkening / Flickr
DuSable Museum of African American History – Self-photographed / Wikimedia Commons
Chicago Botanic Garden – winpod / PixaBay