Chicago is a major city in the state of Illinois in 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 engrained in the history of 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 tour, gangster tour, haunted places tour, street food tour, architecture tour and so on.
It is a city of skyscrapers so city skyline is among the most wonderful things to see in Chicago. There are several buildings which have observation decks for this purpose. You can also take boat cruise tours in Lake Michigan or in Mississippi River to enjoy the architecture of the city. You can also get sailing and kayaking tours. The lake is the epicenter for 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 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 team. 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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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 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 is 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 of 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 the Millennium Park.
4. Chicago Children’s Museum
This museum showcases history through interactive exhibits, games and activities. It is 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 hour’s 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 theatre. You would an hour or two to explore this place when you visit Chicago.
I suggest you must book your ticket of 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 19th and 20th century. 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 a 1000 feet above 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 city becomes a kaleidoscope of lights of various colours with a few patches of darkness. You will need 30 to 45 minutes for this experience.
I suggest you must buy 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 kms 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 by the lakeside.
There are different activities that you can do at Lake Michigan. Here below I have suggested some of activities that you should do at Lake Michigan or Lakefront Trail
- Seadog Speedboat Ride
- Lake Michigan Buffet Brunch, Lunch or Dinner Cruise
- Lake Michigan Skyline Sightseeing Cruise
- Lakefront Segway Tour
- Bike Tour of Lakefront Neighborhoods
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
- Kimpton Hotel Monaco Chicago
- LondonHouse Chicago, Curio Collection by Hilton
- Kinzie Hotel
- The Blackstone, Autograph Collection
- Swissotel Chicago
- La Quinta Inn & Suites by Wyndham Chicago Downtown
- The Godfrey Hotel Chicago
- Sofitel Chicago Magnificent Mile
- W Chicago – Lakeshore
- Radisson Blu Aqua Hotel, Chicago
- Warwick Allerton – Chicago
- theWit Chicago – a DoubleTree by Hilton Hotel
Mid-Range Hotels
- Carlton Inn Midway
- The Chicago Parthenon Hostel
- Heart O’ Chicago Motel
- HI Chicago Hostel
- Villa Dubois Guest House
- Hostelling International Chicago
- Chicago Lake Shore Hotel
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 the airports are connected with CTA trains. O’Hare is connected through Blue Line and Midway through Orange Line.
The Midway Airport majorly receives domestic flights from cities in 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 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 USA such as Milwaukee, St Louis, Omaha, Denver, Salt Lake City, San Francisco, Washington, 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 most cool 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
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