The TOP 10 Things to do in Chicago

The bean Cloud Gate Chicago

The TOP 10 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 top 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!

Discover now the 10 best activities to do in Chicago!

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

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

My secret tip: 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.

The Bean has to be at the top of your list of the best things to do in Chicago!

Location: Cloud Gate

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! Therefore it’s one of the best places to see in Chicago!

Location: Magnificent Mile

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. I can only recommend it to you in the best things to do in Chicago!

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).

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! But this is one of the best things to do in Chicago whatever the season! It’s also stunning when the river is frozen in winter.

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

My secret tip: 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.

Location: Chicago Riverwalk

Be amazed at 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! If you are not afraid of heights you will love it as one of the best activities to do in Chicago! And I also added it to my list of the best photo spots in the city!

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.

FYI the entrance of the Skydeck is available with the Chicago CityPASS tickets . It 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! I recommend it if you

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

Location: Skydeck

My secret tip: come here at the opening in the morning to avoid the crowds. Or at the end of the day to enjoy the sunset from here (but it’s more crowded)!

Visit the Art Institute of Chicago

The Art Institute of Chicago 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. You shouldn’t miss it in your list of the best things to do in Chicago if you are a culture buff!

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

Opening hours: 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

Location: Art Institute of Chicago

My secret tip: I especially 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.

Enjoy breathtaking 360 degrees views of Chicago at 360 Chicago

This is another place to enjoy Chicago from above and one of the best activities in town! 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!

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).

My secret tip: Wondering which one to visit between The Skydeck and 360 Chicago in case you do not have time for both? I personally prefer my experience at the Skydeck because I could stand in the amazing glass balconies!

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. And in winter you can admire Lake Michigan all frozen: some very impressive sceneries!

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: Beaches of Chicago


North Avenue Beach

Ohio Street Beach

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: Navy Pier

Location: Navy Pier

Eat like a local

Chicago has some pretty good 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. So, you cannot leave Chicago without trying one of these local treats: one of the best things you can do in Chicago!

Deep Dish Pizza

Deep dish pizza Lou Malnati

The most famous Chicago specialty 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.

My secret tip: 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!

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, 1940s Gangster themed. It’s pretty cool!

Popcorn from Garret

Popcorn from Garrett

Another well-known 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!

In Conclusion…

I am sure you will have fun during your trip to Chicago! Which ones of these 10 best things to do in Chicago are you the most interested in?

You should also take a look at my other articles about Chicago:


Let me know in the comments if you have any questions about the best things to do and best places to see in Chicago!

Save it for later on Pinterest!

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!


Let’s keep in touch!

Follow me on Social Media




  • Pingback:10 Pictures and Destinations that will help you escape from home - Limitless Secrets
    Posted at 14:39h, 01 April Reply

    […] Take a look at my article about Chicago for more info: the TOP 10 Things to do in Chicago […]

  • Holidays from Hels
    Posted at 12:20h, 18 April Reply

    The views over the city look incredible! Would love to see Chicago one day. Really want to check out The Bean! Thanks for sharing.

    • Limitlesssecrets
      Posted at 12:02h, 19 April Reply

      Chicago is one of my favorite city in the US, I definitely recommend to visit! The Bean is really cool you will love it!

  • Charu Goyal
    Posted at 13:47h, 18 April Reply

    I loved this trip of yours so much Ophelie! Such beautiful pictures as always 😍 Chicago is definitely on my bucket list now!

    • Limitlesssecrets
      Posted at 12:04h, 19 April Reply

      Chicago is one of the best American cities I have visited so I highly recommend it! It was even better to discover it with a local!

  • madhu sharma
    Posted at 13:52h, 18 April Reply

    Wow those are some amazing pictures .I haven’t been to Chicago yet, on my next visit to USA,I will surely visit

  • galatia savva
    Posted at 14:40h, 18 April Reply

    Chicago looks incredible, ive only visited Nyc in the states! I feel like im missing out now!

    • Limitlesssecrets
      Posted at 12:31h, 19 April Reply

      Chicago has a lot to offer Galatia! It’s really cool to have the river and the beaches close by!

  • Paula Martinelli
    Posted at 14:48h, 18 April Reply

    I LOVE this detailed itinerary and I am saving for when I finally go to Chicago. I have been living in USA and traveled the whole country, but I cannot believe I haven’t yet been in Chicago. Thanks for the inspiration.

    • Limitlesssecrets
      Posted at 12:06h, 19 April Reply

      Chicago is so cool Paula, you can only love it! I hope you can visit it soon!

  • Katie | KatieGoes
    Posted at 14:56h, 18 April Reply

    I can’t believe that Chicago hasn’t been on my list up until now! Looks fantastic! I must remember to walk up at sunrise for the bean though!

    • Limitlesssecrets
      Posted at 12:06h, 19 April Reply

      It’s better for the experience as you will have it all to yourself Katie! Chicago is really an amazing city to discover!

  • Taylor
    Posted at 16:54h, 18 April Reply

    This is amazing Ophelie! I have been to Chicago once for work a few years back, so I definitely need to go back and truly explore the city. 🙂 I have had Garrett Popcorn before though and it’s so delicious! 🙂

    • Limitlesssecrets
      Posted at 12:08h, 19 April Reply

      I never had such a combo of sweet and savory in a popcorn before! I was surprising but so good! Hope you can go back to Chicago soon Taylor!

  • roshni
    Posted at 17:11h, 18 April Reply

    wow loving that skydeck, the view is amazing

    • Limitlesssecrets
      Posted at 12:08h, 19 April Reply

      It’s really an exceptional experience to be up there! The views are breathtaking indeed Roshni!

  • Caroline Muller
    Posted at 17:28h, 18 April Reply

    Chicago does look like a cool city and that pizza really does look super tasty;

    • Limitlesssecrets
      Posted at 12:09h, 19 April Reply

      This is one of my favorite city in the USA Caro! And that deep-dish pizza is so good! I had a vegetarian version and it was delish!

  • Amy M
    Posted at 17:58h, 18 April Reply

    I was in Chicago last year. It was for work so unfortunately there wasn’t much time for exploring, but it was a great city. Managed to eat some incredible food. ALSO. How addictive are tater tots? I’m new to exploring the US and am completely addicted!

    • Limitlesssecrets
      Posted at 12:10h, 19 April Reply

      I didn’t try the tater tots in Chicago unfortunately, I need to add this to my list Amy! I hope you can go back to Chicago and enjoy more of this amazing city!

  • Shannon
    Posted at 18:00h, 18 April Reply

    Great summary! I couldn’t agree more about the food- Chicago deep dish pizza is the best! And everyone should try an Italian Beef. There’s lot of debate about the best Chicago beef spot, but I agree with you on Portillo’s! The Art Institute is great, I also really enjoy the Field Museum.

    • Limitlesssecrets
      Posted at 12:12h, 19 April Reply

      I am glad we agree on some of the best spots of Chicago Shannon! I have to see that Field Museum next time, thank you for the tip!

  • Kriszti
    Posted at 18:02h, 18 April Reply

    Your pictures are so beautiful Ophélie! I really hope I can visit Chicago this year, it’s such an amazing city. I love high places so I’m sure the Skydeck would be my favourite 🙂

    • Limitlesssecrets
      Posted at 12:12h, 19 April Reply

      You will adore the Skydeck Kriszti! One of the coolest place to take pictures for sure!

  • Linnea
    Posted at 18:10h, 18 April Reply

    All your dresses here are stunning! Chicago is one of my favorite cities! If you visit during baseball season next time you need to see a Cubs game! They’re so fun!

    • Limitlesssecrets
      Posted at 12:13h, 19 April Reply

      Can you believe I have never seen a baseball game Linnea?! It’s definitely on my list for next time!

  • Bettina
    Posted at 18:20h, 18 April Reply

    I absolutely love this post! You have captured the city so well and make me want to go back immediately! These are definitely all my favorite things to do in Chicago as well! Also, your Skydeck photos are stunning! <3

    • Limitlesssecrets
      Posted at 12:14h, 19 April Reply

      Thank you Bettina! It was so awesome to discover the city with you and Talia! I hope we will get the opportunity to meet there again in the future!

  • Polly
    Posted at 18:30h, 18 April Reply

    Love this article. As always your pictures are absolutely stunning, Ophelie. Chicago was on my list for this year, but I think this will have to be postponed. Loved the riverwalk igea. Thank you for the great post! 🙂

    • Limitlesssecrets
      Posted at 12:15h, 19 April Reply

      I am happy I gave you some ideas for your future trip Polly! Hopefully you can visit soon! Also thank you for the compliments!

  • A Capone Connection
    Posted at 21:45h, 18 April Reply

    Your pictures are beautiful! I’ve been seeing so much about the Sky Deck and now I feel like I HAVE to see it for myself. Thank you for sharing your experience!

    • Limitlesssecrets
      Posted at 12:17h, 19 April Reply

      Thanks a lot for the compliments! The Skydeck is such an exceptional experience, you will love it!

  • Jenn - The Solivagant Soul
    Posted at 22:07h, 18 April Reply

    First, let me compliment you on the dresses, so beautiful! Second, I have had Chicago on my go-to list for ages and besides the bean, my main attraction there is to try Chicago-style pizza hahaha. In any case, thank you for all the additional ideas for places to visit. I wont be as fashionable as you but I am sure I will enjoy it anyways!

    • Limitlesssecrets
      Posted at 12:19h, 19 April Reply

      Thank you for the compliments Jenn! The deep-dish pizza is so good, it’s a must to taste it! And I am sure there is no dress code to have fun visiting a place, especially not in Chicago! hopefully you can visit soon 🙂

  • Suzanne
    Posted at 22:17h, 18 April Reply

    Chicago is fantastic city and this is great list to guide visitors to all the best places.

    • Limitlesssecrets
      Posted at 12:20h, 19 April Reply

      I am glad you like my top 10 things recommendations for Chicago Suzanne! Thank you!

  • Alexandra Booze
    Posted at 00:24h, 19 April Reply

    I had no idea that had architecture boat tours! I am going to have to do that next time I am in Chicago. You shed light on a lot of things that I didn’t know were possible to do in Chi Town!

    • Limitlesssecrets
      Posted at 12:21h, 19 April Reply

      The Windy City is full of cool activities and experiences Alexandra! The architecture boat tour was one of my highlights for sure, a way to discover the city from another perspective!

  • Katie
    Posted at 00:46h, 19 April Reply

    Some great things to do in Chicago. I loved the food, the beaches and the architecture when I visited. The architecture boat trip sounds amazing!

    • Limitlesssecrets
      Posted at 12:22h, 19 April Reply

      There are so many cool things to do in Chicago Katie! That’s why I would love to visit again! I really enjoyed seeing the city from another angle with the architecture boat tour, it’s a must!

  • Dani
    Posted at 01:07h, 19 April Reply

    I had the pleasure of travelling to Chicago for work last October, and was so surprised at what an awesome city it was. Your photos are stunning!

    • Limitlesssecrets
      Posted at 12:23h, 19 April Reply

      I didn’t expect to love it so much at first sight either Dani! Now I recommend it to everyone! Thank you for the compliment!

  • Jill Robbins
    Posted at 04:18h, 19 April Reply

    Great tips – I love all your dresses!

    • Limitlesssecrets
      Posted at 12:23h, 19 April Reply

      Many thanks for your feedback Jill!

  • Laura
    Posted at 12:42h, 19 April Reply

    Awesome guide to Chicago – I’d love to visit!

    • Limitlesssecrets
      Posted at 10:35h, 20 April Reply

      Chicago is the kind of city that you cannot forget! I highly recommend it if you are in the USA Laura!

  • Jiayi Wang
    Posted at 13:45h, 19 April Reply

    Love your beautiful shots of Chicago Ophélie!! This is such a useful guide, I’ve saved it and will definitely be reading it again before I make my way to the windy city! 🙂

    • Limitlesssecrets
      Posted at 10:36h, 20 April Reply

      Thank you Jiayi! Chicago is one of my favorite city in the US and has so many things to offer!

Post A Comment

error: Content is protected !!