10 Best Things To Do In Chicago, Illinois – Our Guide to the Top Attractions in Chicago, Illinois

Chicago is the second most visited city in the USA with over 50 Million annual visitors each year. Like a lot of action-packed tourist hotspots, it is not always abundantly clear what to do while visiting the City. But Fear, not the City is packed with incredible sights, attractions, Culture, Cuisine, and Shopping. It’s a real Metropolitan wonderland and should be right up there in most people must see Citys. Our Guide to the Top attractions In Chicago is aimed at guiding you through all the absolute best things to see and do in the City.

10 Best Things to Do in Chicago Illinois

Regardless of what you like to do, our list of 10 Best Things To Do In Chicago, Illinois draws in both tourists and locals, and there is something for everyone. Most of the attractions we spotlight are relatively inexpensive or free and are congregated in or near downtown, allowing for easy use of Chicago’s fabulous public transportation, so there is no need to hail a taxi from stop to stop.

1 – Museums!

Chicago’s rivalry with New York comprises most things in life, buildings, culture, politics, etc… But it even touches their museums. New York is well known as one of the best destinations in the World for Museums, But the truth is Chicago gives it a run for its money! While The offering is somewhat less diverse The Quality is right up there. So Your visit to Chicago really should feature at least one of America’s top Museums.

Art Institute of Chicago

Art Institute of Chicago

Plan for an entire day when visiting the Art Institute of Chicago. This one-million-square-foot mega-museum boasts more than 300,000 permanent pieces in its collection. However, f you don’t have a whole day, you might skip the ancient pottery collection at the front of the museum to get to the highlights of the museum, including the largest Impressionist collection in the world, and the pre-1950 American art gallery, which is home to the most important pieces of art in the building: American Gothic by Grant Wood and Edward Hopper’s Nighthawks. If you plan to scope out the entire complex, go on a Monday or another weekday because the crowds will drive you nuts on the weekends, as you explore art from around the world: Indian, Chinese, Japanese, African, and Himalayan art in the form of sculptures, bronzes, and more.

This Museum is often found in the top 3/4/5 of any list of America’s Best Museums and often in the top 10 in the World! Admittedly it is normally trumped by the Metropolitan Museum of Art in New York…but let’s ignore that!

Field Museum of Natural History

The Field Museum

Department store entrepreneur Marshall Fields hooked up this museum with early funding, so the museum was named after him. While most turn to the Art Institute for their museum fix, those who prefer a look at our anthropological past should visit this Chicago gem. Spread across nine acres, 25 million artifacts call the Field Museum home. Sue is the queen of this castle; she is the largest and most complete record of the Tyrannosaurus Rex in the world. You can also visit ancient Egypt where 20 mummies dwell in an ancient tomb and take a tour through Underground Adventures in which giant insects roam. There are also numerous labs with real scientists studying collected DNA and fossils, as well as a play lab for kids.

The Museum of Science and Industry

Museum of Science and Industry

Stuffy Art museums and dusty collections of stuffed animals are not for everyone. If the last few Museums have bored you rigid the Museum of Science and Industry might be right up your street. The Exhibits here are far more interactive and invite you to be a part of the display. Explore and Replica Mineshaft, Explore a real German U-Boat, or control an actual indoor tornado, Plus a whole lot more in its 14 acres of Exhibit space!


There are loads more Museums in the City, we put together a list of all the best Museums in Chicago so you can see which would suit your family the most.

2 – John G. Shedd Aquarium

shedd Aquarium Chicago

Our loyal readers will know that we like aquariums…we like them a lot. We are more than happy to visit an even less-than-average aquarium to get our fix. However, the Shedd Aquarium is anything but below average! We rank it as number 3 in the States, and that is with some STIFF competition!

The John G. Shedd Aquarium is in a marble building that is octagon in shape and holds a world of water creatures from rivers, lakes, and oceans. The Caribbean Coral Reef is the first adventure in the aquarium, hitting you as soon as you enter the building. The 90,000-gallon tank is a mesmerizing habitat for sharks, sea turtles, stingrays, and barracudas. In addition, you will find a Wild Reef that connects 26 habitats full of sea predators.

There is also a re-creation of the Amazon basin, where you can view piranhas and sleek and colorful jungle frogs. Finally, in the Polar Play Zone, kids can dress up like a penguin and visit real rockhopper penguins, which “bound” instead of wobble and have yellow and black spiky feathers on their heads. Often ranked as one of the top Museums in the USA it’s a real gem and a real must-see in the City!

3 – Lincoln Park Zoo

Polar Bear Lincoln Park Zoo

Speaking of must see’s, The Lincoln Park Zoo is open every day, meaning every day, and it’s FREE. So, on that cold day when everyone is hiding inside warm museums or warming their insides at the local pub, you can put on a few layers and head to the zoo to explore 49 acres of rolling pathways, flower gardens, and of course, a myriad of habitats that bring you an African Journey, a Small Mammal-Reptile House, and a Sea Lion Pool. Nothing is missed in these exhibits, including everything from Pygmy hippos to hissing Madagascar cockroaches. Furthermore, if you do decide to visit during the winter months, you will be met with holiday lights and an ice skating rink.

4 – Ravinia Festival

Ravinia Festival Lawn
Ravinia Festival by Donna Sutton on CC2.0

Chicago has become a festival destination for the culinary world, music, and dance, and the Ravinia Festival is the best of the bunch, due in large part to its location. Ravinia was once an amusement park when it opened in 1904, providing a casino, dance hall, and baseball to the public, but since 1936, it has been the summer home of the Chicago Symphony Orchestra. Now, you can lie on the grass, and as the stars flood the sky, watch exhilarating performances by the Symphony, blues and pop acts, opera, and dance. During the Ravinia Festival, the oldest outdoor festival in the United States, locals bring picnic baskets full of fine food and wines, and their home’s best China, all of which are allowed into the venue with a paid ticket on the lawn for a steal of $15-$45. So, you should do the same. The Ravinia Festival season runs from mid-June to Labor Day, and is a reason to visit all by itself!

5 – Get up High

Chicago and New York have always been Rivals and apart from their political tussles, the Race for the Sky is their most famous battle and the most visible. This rivalry has left both cities with some of the most breathtaking Skylines in the world. And one of the BEST ways to see this is from up high. There are two incredible Obsevatinos Decks available (with a 3rd on the way!), both with their own unique charms. We really advise seeing both and deciding which is best.

Willis Tower Skydeck

skydeck gallery ledge

For 25 years, Chicago’s Sears Tower was the tallest building in the world, and it was the tallest building in the United States up until 2014. Now, the department store chain Sears has filed for bankruptcy, and the tower has been renamed Willis Tower. This historic building has a Skydeck on the 103rd floor, which is made up of a row of glass boxes that hover over the city. The floor is a 1.5-inch glass ledge that gets your heart racing and leaves some folks with an imbalanced equilibrium, but 1.5 million people test the glass floor on a yearly basis. It is the tallest observation deck in America, and you get a staggering 50-mile view that gives you a glimpse of four states.

360 Chicago

360 Chicago John Hancock Tower

Not Quite as high but an arguably better view is the 360 Chicago. Being right in the shore of Lake Michigan you get a fantastic view up and down the coastline. While it is probably a secondary experience to the Skydeck, It’s still a great experience and includes “The Tilt” experience, where you lean against the window that proceeds to tilt outwards giving you a face-first view of the drop below. You also get to see the amazing Willis Tower, which you obviously miss if you are standing on top of it!

Tip – If you are considering an attraction pass, most include BOTH attractions. We suggest doing one in the daylight and the other at night to get the best of both worlds. Better Still time it for Sunset to get a fantastic view of the city as it changes from day to night!

6 – The Parks in the Loop: Grant Park and Millennium Park

Grant Park Chicago
Grant Park Chicago by Marco Verch on CC2.0

The lakefront park system in Chicago is a magnificent metropolitan outdoor environment that ranks among the best parks in the world. Grant Park is the backyard of Chicago, and the city built the park on sandbars and landfills that included the charred debris from the Great Chicago Fire in 1871. The final result was a park that is modeled after the Versailles gardens with giant lawns, paths, plants, and alleys of trees. There are also museums and open spaces that extend from the original shoreline to Michigan Avenue. From Michigan Avenue, on the northwest corner of Rudolph Street, you run into Millennium Park. Meant to inspire a new millennium, the monumental public works project that opened in 2004 is full of brilliant landscaping and architecture, an ice skating rink, and a theater, with the Jay Pritzker Pavilion as its centerpiece. The dazzling building with massive ribbons of spiraling steel seats 4,000 people who visit for free shows all summer long. The park is a cultural nirvana that is welcoming to locals and tourists alike.

7 – Navy Pier and Centennial Wheel

Navy Pier centennial wheel

If you have had enough of Culture, Museums, and Architecture, then the Navy Pier might be the perfect place to unwind. It is unashamedly touristy and offers fun and mild thrills with its rides and attractions. It’s free to enter but the individual attractions will cost. The Main Feature is the 200ft Ferris wheel that provides an incredible view of the Skyline. Most Wednesday and Saturday Evenings there is a fireworks show throughout the summer (May-September) So plan your visit to coincide with this, although queues will be long.

8 – Frank Lloyd Wright Home and Studio Tour

In the early days of its existence, the Frank Lloyd Wright Home and Studio was nothing more than just that; a home and escape for Wright to work his wonders. Wright was an innovative architect – one of the most revered of all time – who developed a style that combined broad horizontals to match Midwest landscapes, natural materials, and the seamless transformation between exteriors and interiors. Over time, his home became the experimental grounds for his suburban vision. Wright’s whimsical lab is full of grand ideas and niches to explore, almost as if you are traveling through the architect’s mind.

9 – The Violet Hour in Wicker Park

The Violet Hour
The Violet Hour by Edsel Little on CC2.0

I am a beer snob of sorts, so I am definitely not put off by a bar that takes alcoholic beverages seriously. Not only does Violet Hour take the art of drinking seriously, but they also make it clear that they don’t want your business if you plan to stare at your phone through the night. In fact, visiting The Violet Hour comes with a few rules that might turn some away. First, this speakeasy-style bar does not allow your black mirror in the joint, with a strict ban on phones in the lounge. Furthermore, there are “No O-Bombs. No Jager Bombs. No bombs of any kind. No Budweiser. No light beer. No Grey Goose. No Cosmopolitans.”

I left mainstream beer behind in college, and I often give long hard stares to folks in my party who spend too much time on their phone, so The Violet Hour was a wonderful escape for this old-timer. Instead of hanging out on Instagram, live in the moment for a bit, and instead of a Bud Light, order some bourbon within a ferocious blend of ingredients called the Scribble Scrabble. Finally, like any solid speakeasy, the door is hard to find, so look for the line of snappy dressers off Damen Avenue in Wicker Park.

10 – The Magnificent Mile

Magnificent Mile
Magnificent Mile by Tony the Tiger on CC3.0

The Magnificent Mile lurks in the background of your visit to Chicago. While the Windy City is ripe with free shows and free landscapes that make your high-priced hotel seem reasonable, the Magnificent Mile is a place to spend whatever is left of your budget on the final day of your trip. The eight-block area on Michigan Avenue, from the Chicago River to Oak Street to the north is something like Rodeo Drive in Beverly Hills or Fifth Avenue in New York City. It is where the rich go to splurge, while the rest of us look upon stroke-inducing price tags of high fashion items. Malls live upon malls here, and boutiques line the streets with great density, along with 19th Century taverns, unique hotels, and other hidden shops that might draw you into their lair.

BONUS – Road Trip!

route 66

We think Chicago is possibly the best city in the world to Start a Road Trip, Why? Route 66! While this iconic roadway can be started in either Chicago or LA, It really should kick off in Chicago as that is the direction most of the original travelers of the route took as they escaped the dustbowl in the north for potential prosperity in the south.

A few days soaking up the culture of this incredible city is the perfect way to get you started and ready for the ultimate USA Route 66 Road trip!

The Final Word on Chicago Attractions: Chicago’s Authentic Experience

the Loop

Chicago is not built on an ocean beach and is not a center for amusement park activities, so touring Chicago is more of an authentic experience that has been built over nearly two centuries. In other words, Chicago “is” the attraction, and you can find complete happiness in just experiencing the city on your first time around.

In fact, you can find cheap and cultural enjoyment by riding the “L,” Chicago’s elevated rail system, to get a great look at the city from a point of view much different from the ground. The Brown Line is your best opportunity to see the city unfold, as the cityscape sits in close proximity to your train window. Offices, apartment buildings, and homes zip by as you skate through urban areas, outer urban areas, and the suburbs.

You can also cheer with the locals at iconic Wrigley Field for a Cubs’ baseball game, or head to Soldier Field for a Bears’ football game. In addition, basketball fans can catch a Chicago Bulls game, hockey fans can turn to the Chicago Blackhawks, for soccer fans there is the Chicago Fire, and there is even a second professional baseball team, the White Sox.

Finally, many magnificent architects lived and performed in Chicago, making the city a study in architecture. Innovative structures throughout Chicago continue to spark the imagination of young designers and awe visitors. Make sure you take notice of every niche of the city as you ramble around Chicago visiting our choices for the best attractions.

On a Budget? Check out our choices for the best FREE attractions in the City

Have Your Say?

Let us know your Favourite things to do in Chicago. Do you agree with our List? Have we missed something out? Have we included an Attraction you hate? Let us know in the comments below! Or if you have any questions just drop us a comment we would love to hear from you!

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