25 Best Things To Do In Chicago (IL)

Chicago, fondly referred to as the Windy City, is action packed with culture which include art, film, theater, music and comedy, and is also home to some fairly awesome sporting teams. This Illinois city with over 2.7 million residents as of 2012 is the third largest city in the United States. Famous too for its fabulous, iconic buildings and skyscrapers, the city draws in over 50 million domestic and international visitors a year. Why not be some of them yourselves?!

Let’s have a look at the 25 best things to do in Chicago:

1. Art Institute of Chicago

Art Institute of Chicago

Source: grayline

Art Institute of Chicago

Chicago Art Institute is North America’s pride and joy, with over 300,000 works of art in its permanent collection which include a complication of Impressionists and Post-Impressionist art as well as the institute hosting 30 special exhibitions and hundreds of gallery events, lectures, performances and talks every year. Founded in 1879, it is popular with everybody, locals and visitors alike. Whether you enjoy photography (drop into the expansive photography section) to the weird and wonderful (The Nighthawk and American Gothic) the whole family will appreciate a visit here, which is also very child friendly.

2. Millennium Park

Millennium Park, The Bean

Source: flickr

Millennium Park, The Bean

The Millennium Park offers 25 acres of interesting architecture, pretty landscape and a fascinating collection of public art. The park celebrated its 10th anniversary in 2015 and remains popular as it continues to stage dozens of free programs and events, which include outdoor concerts and films screenings, to name just a few. A trip to the park will be a fun outing for everyone, with a walk around the Lurie Garden; an urban oasis paying homage to Chicago’s motto “Urbs in Horto,” or City in a Garden, to grabbing a bite to eat at the Park Grill restaurant, or enjoying a picnic on the main plaza in the spring and summer months.

3. Wrigley Field

Wrigley Field

Source: flickr

Wrigley Field

One of the oldest National League ballparks, Wrigley Field, nicknamed ‘The Friendly Confines’ by Hall of Fame personality Ernie Banks, has a seating capacity of 42,495 and was home to the renowned Chicago Bears of the NFL between 1921, and 1970. It is now home to the Chicago Cubs, one of Chicago’s two Major League Baseball (MLB) franchises. Built originally in 1914 for the Chicago Wales, it was taken over by chewing gum magnate William Wrigley, Jr. in 1921. Besides enjoying a game, why not take the family for a ‘behind the scenes’ tour of the iconic grounds? You can have a fabulous time hearing all about the field and the various players from one of the venue’s very informative guides.

4. 360 Chicago Observation Deck

360 Chicago Observation Deck

Source: 360chicago

360 Chicago Observation Deck

This 100 story, 1,127 ft skyscraper is situated in the John Hancock Center. When the building was finished in 1968 it was then the tallest building in the world outside of New York City. These days it is the fourth tallest building in Chicago and the seventh tallest in the U.S. It is home to offices, restaurants and about 700 condominiums. Talk about living the high life! The 360 Observation Deck which is situated on the 95th floor, has a café and bar, together with an open air Sky Walk (Chicago’s only) offering a breathtaking view of downtown Chicago and its lakefront, extending as far away as four neighboring states! And for the very brave members of the family, don’t forget the Tilt, which leans out over the city from one of the windows!

5. Museum of Science and Industry

Museum of Science and Industry

Source: wikipedia

Museum of Science and Industry

Known to be the largest science museum in the western hemisphere, a trip to the Museum of Science and Industry is one way for the family to spend some time learning and exploring all manner of subjects. Some of its truly awesome exhibits include the Apollo 8 spacecraft that had carried the first humans to orbit the Moon, the first diesel-powered stainless-steel passenger train (Pioneer Zephyr), a full-size reproduction coal mine in which the kids can enjoy the Coal Mine Ride and, last but far from least, a U-505 German submarine captured during WWII!

6. Michigan Avenue

Skyscrapers Along the Michigan Avenue Bridge

Source: flickr

Skyscrapers Along the Michigan Avenue Bridge

As the home of high-end shopping area the Magnificent Mile as well as being close to a variety of city attractions, Michigan Avenue is a well known destination for both Chicago natives and visitors to the city. Clean and safe with wide sidewalks, this is a comfortable area in which to employ your credit card! You will find every upscale store imaginable here, as well as plenty of restaurants and coffee shops in which to count the day’s (monetary) damage! From women’s apparel to men’s sporting outlets and plenty of shops to interest the kids, it will be very easy to spend some quality family time here!

7. The Magic Parlour

The Magic Parlour

The Magic Parlour became a regular weekly attraction at the House Theater of Chicago after a winning performance by magician Dennis Watkins who, with his astounding card tricks and other clever capers, managed to win over the audience with his crafty delivery of classic magic entertainment. He has entertained guests from all around the globe and now doing the same for his Chicago audience. The number of guests at the revue is limited, so everyone has a chance to get a good view. He also uses quite a few members from the audience to assist with his tricks, which is great fun for all!

8. Cloud Gate

Cloud Gate

Source: flickr

Cloud Gate

Cloud Gate is a public sculpture cast by Indian-born British artist Anish Kapoor. The very unusual piece is actually the centerpiece of Millennium Park’s AT&T Plaza and draws in tourists from everywhere. Nicknamed The Bean because of its shape, it consists of 168 stainless steel plates that were welded together, with its amply polished exterior having no visible seams. It weighs almost 100 tons and is a great talking point! You can walk around and under its 12 ft high arch where you will be able to see the sculpture’s concave chambers that multiply reflections, and see not only yourselves reflected but also the city’s wonderful downtown skyline.

9. Chicago Pizza Tours

Chicago Pizza Tours

I couldn’t imagine visiting Chicago without indulging in one of the city’s famous pizzas, and a fun way of doing so would be to take a tour of the city’s famous offering! Chicago Pizza Tours will transport you to four different pizza restaurants to sample four very different pizzas, from deep dish to newer recipes and, along the way, the very informative tour guide will be there to tell you lots of fascinating and fun facts about Chicago and its history. You will be able to order drinks at your stops and even get some pizza to take home with you. The kids will love it – not to mention the adults!

10. Shoreline Sightseeing

Shoreline Sightseeing

Source: flickr

Shoreline Sightseeing

This is an excellent way for the family to see Chicago – by water! Seated atop the 100 plus passenger boat, you will be able to both understand and appreciate the marvelous city from a different view. As you sail past the classical and modern buildings, Shoreline Sightseeing’s guide will provide you with seventy five minute’s worth of informative and entertaining anecdotes as well as lots of up to date news all about the city’s future constriction. Taking this tour is sure to provide the family with some terrific insight and historical perspective about Chicago.

11. Chicago Cultural Center

Chicago Cultural Center

Source: flickr

Chicago Cultural Center

Opened in 1897, the center is a true city landmark and worth a visit, if only to admire the building’s Tiffany mosaic glass dome and stunning Italian marble! There is loads more to it than that, of course, particularly when you learn that the center features over 1,000 exhibitions and programs that cover an enormous range of literary, performing and visual arts, not to mention witnessing presidents and dignitaries passing through its gracious doors. It is also headquarters for the Chicago Children’s Choir so check if there are any performances while you are visiting the city. Entrance is free and you might even be fortunate enough to stumble into a piano recital or so! The whole family will enjoy the architecture and exhibits within this wonderful historic building.

12. Holy Name Cathedral

Holy Name Cathedral

Source: flickr

Holy Name Cathedral

Holy Name Cathedral has replaced the Church of the Holy Name and the Cathedral of Saint Mary, both of which had been destroyed in the Great Chicago Fire of 1871. In 1875 it was then dedicated. The church has some beautiful woodwork as well as “Red Hats” of past Cardinals that hang from the church’s rafters, together with a striking pipe organ. A number of influential Cardinals have had their seat here too. There are also a few notorious landmarks within the surrounding area which include a cornerstone inscription still bearing the marks of the murder of Hymie Weiss, the infamous North Side Gang member, who had been killed on the street opposite on October 11, 1926.

13. Maggie Daley Park

Maggie Daley Park

Source: flickr

Maggie Daley Park

A positive force behind many of Chicago’s non profit organizations, the park’s namesake, Maggie Daley, worked hard to improve the lives of children in many ways, including programs like After School Matters, which is now the nation’s biggest teenage out of school program. The park is truly a marvelous venue for the family to spend some fun time in, offering all sorts of outdoor amenities such as tennis courts, picnic area, ice rink and play area for all ages with sand, slides, swings and jungle gyms; in fact, everything you can imagine to keep the kids amused!

14. Trapped In A Room With A Zombie

Zombie

Source: thesixthirty

Zombie

Sounds scary? Actually it’s really not! More of a fun, challenging and unique experience for the adults and teens of the family! Consisting of riddles and puzzles that the family has to solve before the zombie is released into the room in which you’re trapped, this wonderful family team building experience just builds and builds as you encounter all the twists and turns and creative clues which will help you escape. The staff are helpful too and great at pairing up extra members to make up a full team.

15. The Field Museum

The Field Museum

Source: flickr

The Field Museum

This is one of the largest natural history museums in the world, attracting up to 2 million visitors every year who come to see the museum’s extensive collections that is made up of over 24 million objects and specimens including about 275,000 books and journals, gems, meteorites, fossils and cultural artifacts from around the globe. The museum caters for all ages, too, from the handy soundproof room where kids can play some instruments to a small Adobe hut with corn, a Galapagos movie, marvelous dinosaur information and a small area where the little ones can be read to. A must visit for all the family.

16. Lincoln Park Zoo

Polar bear at Lincoln Park Zoo

Source: flickr

Polar bear at Lincoln Park Zoo

Founded in 1868, this is one of the oldest zoos in North America. It is also one of the few free admission zoos (always a nice to know!). The zoo is home to approximately 1,110 animals made up of 200 species, including polar bears, gorillas, monkeys and chimps, reptiles, penguins, and the big cats. The zoo caters for all ages, with carousel rides and a small ice skating rink, as well as a friendly café offering reasonably priced food. There is a well stocked gift shop too. Nicest of all, by walking on the boardwalk at the back of the zoo, you will see some of the best views available of the stunning Chicago Skyline!

17. Lookingglass Theatre Company

Lookingglass Theatre Company

Source: wikipedia

Lookingglass Theatre Company

The Lookingglass Theatre Company was founded in 1988 by graduates of the Northwestern University, whose (successful) aim was to create and present cutting edge theatrical works. The theatre’s main aim is set to reconfigure the stage and audience so each performance is different. There is well spaced and comfortable seating for 240, 60 of whom can sit at balcony level. There are some wonderful performances by world class actors that would be appealing to all the family.

18. Shedd Aquarium

Shedd Aquarium

Source: flickr

Shedd Aquarium

The Shedd Aquarium was for some time the world’s largest indoor aquarium with 5,000,000 US gallons of water, and welcomes over 2 million visitors a year who come to view its amazing 1500 species, which include fish, marine mammals, amphibians, birds, snakes and insects. The aquarium also put on some exciting events that will please all the family, including watching staff train the majestic Beluga whales, dolphins having fun showing off as they love to do, and more. Best of all, the aquarium allows you to get up close with many of its residents, both in and out of the water!

19. Buckingham Fountain

Buckingham Fountain

Source: flickr

Buckingham Fountain

Buckingham Fountain is one of the largest fountains in the world and certainly worth a visit while you are in Chicago! Inspired by the breathtaking Latona Fountain at the Palace of Versailles, the fountain, designed by beaux arts architect Edward H. Bennett, is surrounded by four sea horse statues created by French sculptor Marcel F.Loyau that symbolize the four states – Illinois, Michigan, Wisconsin and Indiana in an allegory to Lake Michigan itself. Built in a rococo wedding cake style, this stunning fountain can be enjoyed year round, with pretty water and evening color light shows during the months April to October, and during the winter, decorated with festive light.

20. Oriental Institute Museum

Oriental Institute Museum

Source: uchicago

Oriental Institute Museum

The Oriental Institute is the perfect attraction for those interested in the history, archaeology and art of the ancient Near East. Established in 1919 it is used by the University of Chicago as its research center for this fascinating period. The museum showcases interesting objects that had actually been excavated by the institute, and include remarkable items relating to ancient Egypt, Persia, Syria, Nubia, Mesopotamia and Anatolia such as religious and royal artifacts as well as everyday objects like tapestries, fabrics and furniture. The Egyptology room is guaranteed to leave you spellbound with their massive statue of King Tut. There is even a mummified baby crocodile to see! The museum also features a very good gift shop with publications and souvenirs, and fun items for the kids, like coloring books and stickers.

21. Lincoln Park

Lincoln Park

Source: flickr

Lincoln Park

Named after US President Abraham Lincoln, Lincoln Park is a great spot for the whole family to enjoy. From its colorful conservatory to the inclusion of its (free) zoo, and from its ice skating rink to its many jogging and running trails plus its lagoon, this large public park is a popular family and friend meeting place. If you are here over the winter season holidays you will be able to enjoy the famous zoo lights placed all around the zoo as well as the park’s Christmas music. Whatever time of year you visit though, you will always have a wonderful view of Lake Michigan and Chicago’s beautiful skyline!

22. Jazz Showcase

Jazz Showcase

Source: flickr

Jazz Showcase

Jazz aficionados in the family should try not to miss an evening at the Jazz Showcase!

This national treasure was founded in 1947 by Joe Segal and now owned and operated by Joe’s son Wayne, and, as you walk through the door, you will feel as if you were walking in the footsteps of some of the most famous jazz players ever. From great names such as Count Basie to Dizzy Gillespie (who had appeared there on his birthday for many years), dropping by to enjoy an evening of jazz entertainment is a must. There is live music 7 nights a week, with the club’s 4 pm Sunday Matinee geared towards families (with free admission for kids 12 and under).

23. Garrett Popcorn

Garrett Popcorn

Source: flickr

Garrett Popcorn

Why not drop into Chicago’s iconic Garrett’s Popcorn shop for a savory reminder of your visit? Imagine a store that specializes in popcorn and sells nothing but! Have fun choosing from Garrett’s gourmet popcorn which is all handcrafted throughout the day in old fashioned copper kettles. Founded in 1949, Garrett’s has grown from strength to strength (or should I say from kernel to kernel?). Choose from their plain, buttery, cashew, almond, caramel, pecan or macadamia crisp (and if that isn’t enough choice, check out their seasonal flavors that appear from time to time too!).

24. Amazing Chicago’s Funhouse Maze

Chicago's Funhouse Maze

Source: flickr

Chicago’s Funhouse Maze

Certainly not your average 30 second maze by a long shot, the Amazing Chicago Funhouse Maze on Navy Pier is 4,000 sq. ft. of light and tunnel effects, mirrors & interactive family fun! Everyone will have a blast venturing through the Rainbow Tunnel, Funny Floor, Mirror Maze, Big Squeeze and other mind blowing puzzles. Suitable for all ages, kids will especially enjoy Time Freak which challenges players to complete against the clock and Atomic Rush, where you will pick a color and the chase it around the game arena – as long as it’s your color, of course!

25. Wander Bikes Chicago Electric Bike Tours & Rentals

Wander Bikes Chicago

Source: wanderbikes

Wander Bikes Chicago

For a healthy and fun way to see Chicago, Wander Bikes is the only tour in the city that extends from Grant Park to Wrigley Field. It might sound like a long way but actually Wander Bikes electric bikes will be doing all the hard work for you! You have the choice of two tours, one where you will be traveling 15 miles (though it will feel like 5 miles on a conventional bicycle) and lasts two and a half hours, the second 10 miles (feeling like 3 miles) for just under the same time. You will ride past many of Chicago’s major landmarks, sights and buildings as you really get a feel for this wonderful city. The tour is suitable for ages 16 and over.

Where to stay: Best Hotels in Chicago, Illinois (IL)
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25 Best Things To Do In Chicago (IL):

Millennium Park, The Bean