The TOP 10 Things to do in Chicago

The bean Cloud Gate Chicago

The TOP 10 Things to do in Chicago

Here are the top 10 of the best things to do in Chicago!

I have spent 2 weeks in Chicago for the first time at the beginning of Fall 2019 and I enjoyed it a lot! Therefore I have gathered here a list of the 10 best things to see and do in Chicago!

This American city located in the state of Illinois on the shores of Lake Michigan has a lot to offer. For me it was love at first sight! The skyline is amazing and the architecture of the skyscrapers is stunning. The presence of the Chicago River in downtown adds a lot of value the city. That one of the reasons why it makes it very pleasant to discover!

Travel tip: the Chicago CityPASS tickets will allow you to see the top 5 attractions with savings over regular admission prices. You can purchase it online or buy it at any of the partner attractions. It will also help you to skip many ticket lines!

More info here:

1. See The Bean and Millennium Park

The most famous landmark of Chicago is Cloud Gate.
This sculpture is nicknamed The Bean because of its shape. It’s pretty cool to capture it because of the reflection of the skyline of Chicago inside it.

You should walk around and below to experience it to the fullest!

If you go there at sunrise you will have the opportunity to have it all to yourself. Indeed it gets pretty crowded during the day.

Once you are there, you can wander in the alleys of Millenium Park as this green space is full of other installations and things to see: the Millennium Monument, the Jay Pritzker Pavilion, the Crown Fountain, the Lurie Garden and more.

More info here:

2. Walk the Magnificent Mile

The Magnificent Mile is a 13-block section of North Michigan Avenue running from the banks of the Chicago River to the south to Oak Street to the north.

Not only Chicago’s largest shopping district, you will also find there a lot of restaurants, hotels and attractions including shows, theaters, galleries, museums and tours!

More info here:

3. Do an Architecture Boat Tour

The architecture in Chicago is very impressive and makes the reputation of the city worldwide! One of the best ways to take in all of the stunning buildings is from the river or Lake Michigan. Therefore you will find many boat tour offers.

I got on board with Shoreline Sightseeing and cruised the Chicago River during 75 minutes to learn about the city’s vibrant history.

It was very insightful and funny! From hidden architectural treasures to the city’s most famous landmarks, the expert guide told us how Chicago’s buildings, architecture and engineering made the city famous.

More info here:

Prices: Adult prices, Monday – Thursday $37, Friday & Sunday $39, Saturday $41, Holiday & Special Events $43. Child prices, Monday – Thursday $19, Friday & Sunday $20, Saturday $22, Holiday & Special Events $24. Infant(s) free, (taxes not included).

4. Stroll on the Riverwalk

One of the things I like the most about Chicago is that you can walk along the river. The Chicago Riverwalk is an open, pedestrian waterfront located on the south bank of the main branch of the Chicago River in downtown Chicago. I was lucky enough to experience a sunny weather during my visit and it was very nice to wander here!

It’s open from 6am to 11pm and you can find restaurants, park seating, boat rentals, and other activities.

In the evening, from Wednesdays to Sundays, a video installation takes over the side of the Merchandise Mart. The projections with images and colors begin approximately 30 minutes after sunset and run for approximately 2 hours.

More info here:

5. Be amazed with the spectacular views from the Skydeck

On the 103rd floor of the Willis Tower you will find the Skydeck. This is the highest observation deck in the United States!

The elevators reach the top in about 60 seconds. Up there you will have the incredible opportunity to stand in The Ledge: 4 glass balconies, which extend approximately 1.2 m (4.3 feet) from the façade at 410 meters (1,353 feet) in the air. They will allow you to see the streets below. It is very impressive!

The Skydeck offers unbeatable views of the city and beyond: you can see parts of 4 different states (Illinois, Wisconsin, Indiana & Michigan), Soldier Field, Chicago River and more.

CityPass: the entrance of the Skydeck is available with the CityPass!

More info here:

Admission: Adult – Ages 12 and up $25.00, Youth – Ages 3 to 11 $17.00, Children under 3 are free

6. Visit the Art Institute of Chicago

This museum is one of the oldest and largest art museums in the United States. Its permanent collection of nearly 300,000 works of art, includes iconic works such as Georges Seurat’s A Sunday on La Grande Jatte, Pablo Picasso’s The Old Guitarist, Edward Hopper’s Nighthawks, and Grant Wood’s American Gothic. It is augmented by more than 30 special exhibitions every year.

I particularly enjoyed the following collections: the American Art section, the Impressionist and Post-Impressionist paintings from the European Art section, and the Modern and Contemporary Art section.

CityPass: the entrance of the Art Institute is available with the CityPass!

More info here:

The museum is open daily 10:30–5:00 and Thursdays until 8:00.

Pricing: Adult $25.00 (includes tax), Students and Teens (14–17 years) $19.00 (includes tax) – Free for children

7. Enjoy breathtaking 360 degrees views of Chicago at 360 Chicago

This is another place to enjoy Chicago from above! The 360 CHICAGO observation deck is located 1000 feet above the famous Magnificent Mile in the iconic John Hancock Building. Here you can get 360 degrees views of the city: Navy Pier, Lake Michigan, Magnificent Mile and more.

I enjoyed the interactive learning opportunities on the city’s rich history and iconic architecture.

If you want to spice up your visit you can try The Tilt: an enclosed, glass and steel moveable platform. It will slowly tilt outward to an adventurous angle, generating downward-facing views of Chicago – from 310 meters (1,000 feet) above The Magnificent Mile.

CityPass: the entrance of 360 Chicago is available with the CityPass!

More info here:

Wondering which one to visit between The Skydeck and 360 Chicago? Check this website: I personally prefer my experience at the Skydeck because of the glass balconies.

Opening hours: every day from 9:00am to 11:00pm, last entry at 10:30pm

Pricing: Adult – 12+ years $22.00 (includes tax), Youth – 3–11 years $15.00 (includes tax). Tilt: $8 (includes tax)

8. Go to the Beach

Yes Chicago has beaches! It’s really amazing to be able to escape from the busy city in only a few minutes. During Spring and Summer this is the perfect place to relax, to stroll and to workout.

You will find sandy lakefront hangouts all along the coast of Lake Michigan. I went at North Avenue Beach and in Ohio Street Beach and I loved them both! Those two beaches will offer you great photography spots with epic views of the skyline: at the end of the jetty in North Avenue beach and in Olive Park close to Ohio Street Beach.

More info here:

9. Have fun at Navy Pier

Navy Pier is located on the Chicago shoreline of Lake Michigan. There are more than 50 acres of parks, gardens, shops, restaurants, family attractions and exhibition facilities. It is one of the most visited attractions in the entire Midwest and is Chicago’s number one tourist attraction!

More info here:

10. Eat like a local

Chicago has some pretty cool food specialties! Here are 3 of them that I had the pleasure to taste: deep-dish pizza, Chicago-style hotdog and the popcorn from Garret.

Deep dish pizza Lou Malnati

Deep Dish Pizza

The most famous one is a very special pizza named deep-dish pizza. Its crust is very deep, creating a very thick pizza that resembles a pie or a quiche more than a flatbread. Deep-dish pizza is baked in a round, steel pan that is close to a cake or pie pan.

I tried one at Lou Malnati’s Pizzeria and chose The Lou (a vegetarian version). I really liked it but you have to know it is very filling. We ordered a medium version with 6 slices and we took half of it to go as we could not finish it!

More info here:

Chicago-style hot dog

Portillo's menu - Chicago

Chicago also has its own version of the hot dog. The Chicago-style hot dog includes the all-beef sausage on a poppy seed bun and is topped with mustard, onions, sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. The complete assembly of a Chicago hot dog is said to be “dragged through the garden” due to the many toppings!

I ate one at Portillo’s, a chain specialized in in serving Chicago-style food such as hot dogs, Maxwell Street Polish, and Italian Beef. I went to the restaurant located in 100 W Ontario St. Each Portillo’s location is decked out in the theme of a different decade and this particular location is 1930s, ’40s Gangster themed. It’s pretty cool!

More info here:

Popcorn from Garret

Popcorn from Garrett

Another well-know specialty from Chicago is the popcorn from Garret. Garret has a unique mix that combines caramel and cheddar cheese popcorns. This pretty surprising duo of sweet and savory flavors is actually quite good!

More info here:

I am sure you will have fun during your trip to Chicago!

If you are visiting Chitown, make sure to check the website of ChooseChicago! This is the official destination marketing organization for Chicago. You will find there plenty of useful information about things to do in Chicago and how to organize your trip there!

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About Me

Hello! I am Ophélie, an avid traveller, photographer and foodista. I am French and I live in Paris.

This blog, will give you all my secrets: my best addresses (sightseeing and food) all around the world and in Paris, and my travel and lifestyle tips!


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