Ultimate Chicago Bucket List You’ll Want to Steal (2024)

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Cloud Gate

Chicago Bucket List 

Chicago is one of my favorite Midwestern cities that has a big city feel with local charm. There can be so much to see when visiting Chicago, so I made this simple Chicago Bucket List that includes the top things to do in Chicago and some restaurants and rooftops in Chicago that you have to check out.

I also have an in-depth travel guide of Chicago & Chicago Instagram Spots blog posts you should read after this! 

> For reference, check out the map down below to see where everything I mentioned is located!  

Stay at Hotel with a View

London House Chicago


85 E Wacker Drive

LondonHouse ChicagoThe LondonHouse, located in the heart of Downtown Chicago, has the most stunning views that will make leaving the room a hard decision. You’ll be able to see the Chicago River and it’s many bridges with floor to ceiling windows, just be sure to book a river view.

LondonHouse is a luxury lifestyle hotel with a tri-level rooftop bar, restaurants, and a spa. It’s located in a historic landmark building, and it’s only a 10-minute walk from Millenium Park. The rooms feature updated finishes, sleek modern design, and amazing views

Lunch on the Beach

Shore Club Chicago

Shore Club Chicago ($$$) 

1603 N. Lake Shore Drive

Shore Club Chicago: Have lunch on the beach, are we still in Chicago? Shore Club Chicago offers an experience rivaling those of the best beaches from around the world.

Whether you want to enjoy drinks and appetizers outside in a cabana or have a fun lunch inside the open-aired dining space you’ll have unparalleled views of Lake Michigan. Sample your favorite Mediterranean dishes like yellow beet hummus, salmon ceviche, and lobster tacos with mega-sized pineapple copper cocktails.

This spot is perfect for a girls’ trip, couples, and friends who want to have a fun day out!

Walk Michigan Avenue

In need of some shopping? Walk down Michigan Avenue to shop until you drop. You can find high-end shops like Gucci and Louis Vuitton and other favorites like Zara. 

Chicago Architecture River Cruise

Chicago River Cruise

Chicago’s First Lady Cruises

112 E. Wacker Drive 

Learn more about Chicago’s famous architecture on a 90-minute Chicago Architecture River Cruise (CAFC River Cruise). It’s the #1 tour in the city based on TripAdvisor. All tour guides are highly trained and passionate volunteer docents that provide information that you might not have known about Chicago. 

From the river, you can get the best views of the unique architecture, plus there is a bar if you want to enjoy a drink as you cruise! 

Tickets start at $46.29

Visit Skydeck Chicago

skydeck chicago

skydeck chicago

Skydeck Chicago 

233 Wacker Drive 

To get sky sweeping views of Chicago, heading to the Skydeck Chicago on top of the Willis Tower is a must! Situated 103 floors above the city, only the brave will walk over the ledge that’s literally a glass box that protrudes from the building. 

The Skydeck Chicago offers unparalleled 360-degree views of the city! Recently the building has undergone a renovation that updated the queue to get in. After the tower enjoy some food in the new gorgeous lobby with favorite eats like Shake Shack, Sweetgreen, Brownbag Seafood, Starbucks, and more! 

Ticket Prices are children to adult $22-$26. 

Walk Through Millennium Park 

Chicago Bucket List

Stroll through Chicago’s Millennium Park which is an award-winning center for art, music, architecture, and landscape design. 

Be sure to take a photo at Cloud Gate (aka the Bean) which is an Instagram-worthy public sculpture by British artist Sir Anish Kapoor. You can get some fun photos with the reflection of the city mirrored in the reflective material. 

Currently, there are barricades up to promote social distancing, but you can still enjoy the view with no one in your photo! 

Afternoon at the Art Institute of Chicago 

Art Institute of Chicago

111 S. Michigan Avenue 

The Art Institute of Chicago in Millenium Park is home to the greatest collection of Impressionist paintings outside of Paris, and just recently re-opened to visitors. You can see famous works from Monet, Renoir, Seurat, and Van Gogh. And in the Modern Wing see works from Chagall, Dalí, Matisse, Picasso, and Pollock. 

You’ll have plenty to discover here and it’s the perfect way to add some art to your afternoon! 

Tickets for non-residents are $25 per adult, and $19 for seniors, students, and teens. Free for children under 13. 

Explore Lincoln Park Chicago


Lincoln ParkLincoln Park is one of the most sought out neighborhoods in Chicago and it’s a beautiful place to do some window shopping on Armitage Street, and dine in at some instagrammable restaurants. 

Lunch at Summer House Santa Monica

Summer House Chicago

Summer House Chicago

Summer House Santa Monica ($$)

1954 N. Halsted Street

Summer House Santa Monica gives you an escape to the warmth and laid-back vibes of the West Coast. The menu features market-driven ingredients, local and sustainable farming, and a bakery!

Of course, I had to try my favorites including tuna tare-tare and Avocado Toast. Plus the cocktails are worth mentioning. I could tell all the ingredients were fresh. My favorites were “Prickly Paradisewith Rosa Tequila, prickly Pear, Lime & Black Salt & “Cuz Baby Your a Firework” Mezcal, almond orgeat, blood orange, sour. 

This place does get busy, even for lunch, so be sure to make a reservation in advance. 

Create a Custom Handbag at Laudi Vidini 

Chicago Bucket List

Laudi Vidni 

1007 Armitage Street

I always love some fun shopping when traveling, and I always look for something unique to the destination I am visiting. And in Chicago, you have to visit Laudi Vidini. Spelled Individual backward, at Laudi Vidini you can create your own handbag.

First, you can choose your silhouette from small clutches to larger bags. Then you select your leather out of 50 swatches. After you finish off your bag with choosing your hardware and lining. Prices start at $100 depending on the size and leather chosen.

While Chicago is the only location, you can order a custom bag online and have it delivered worldwide. 


Try Deep Dish Pizza

Giordano’s Chicago

It’s not a trip to Chicago without trying Chicago’s Signature Deep Dish pizza. Head to the source at Giordano’s, where you can find locations throughout the city. 

Opened in 1974 on Chicago’s historic South Side, and for 35 years critics announced Giordano’s has been serving the “best” stuffed pizza. 

But what is deep-dish pizza? It’s made up of two layers of rust filled with ricotta cheese and your favorite additions like mushrooms, onions, etc. Then it’s topped with their signature sauce on top. Definitely a stuffed Pizza. 

Each pie is made on-site fresh so it does take 45 minutes to prepare. Be sure to get your cameras ready for when the cheese sleeve pulls apart. It’s very filling so bring some hungry friends along! 

Check out the Food Scene 

Vermillion ($$$) 

10 W Hubbard Street

Vermillion is a modern Indian Cusine that incorporates Latin Fusion. The cocktails here were super unique, my favorite being the spicy “Bollywood Number”. I am still thinking about the Tandoori Skirt Steak and Blackend Tamarind Ribs, so delicious. If you are looking for something new to try and like the idea of a fusion restaurant it’s a must-try.  

Monteverde ($$$) 

1020 W. Madison Street

Located in Chicago’s West Loop neighborhood, Monteverde is an Italian Restaurant with beautiful decor that blends the traditions of Italian culture and cooking from Chef Sarah Grueneberg’s travels and family heritage. 

Favorite dishes included Stuffed Squash Blossom, Creamy Buratta, and Potato-Filed Žlikrofi. Definitely make a reservation for dinner. Outdoor patio seating is also available as well for a nice evening out. 



1462 E. 53rd Street 

Virtue is a Southern American restaurant that leads with hospitality and kindness. Located in a chic contemporary space with an open kitchen, Chef Erick Williams, chef at Virtue offers elevated southern comfort food in unique ways. 

The CB & J, an upscale classic but this time with cashew nut butter and tomato jam, was delicious for an appetizer. And I loved the Blackend Catfish for dinner. Be sure not to skip out on dessert! A must-try in Chicago. 


Rooftop Bars in Chicago

End the night with sweeping views of Chicago at one of Chicago’s rooftop bars. 

Z Bar at the Peninsula Hotel 

Chicago Bucket List
Z Bar

Enjoy amazing views of the Hancock Tower and Michigan Avenue at Z Bar! I went right at 5 PM so it wasn’t that busy but it’s always best to make a reservation. The service was incredible, and the views were stunning! You can take a cocktail class, just ask ahead. 

LH Rooftop

Rooftop Bars Chicago

Rooftop Bars Chicago
LH Rooftop

Located on top of the LondonHouse is LH Rooftop. Be sure to make a reservation as the line to get in is pretty much busy the entire day. (Due to Covid, no bar seating or standing is available, only tables) But once on top, the views are beautiful and worth the wait!

Nobu Rooftop

The latest rooftop in Chicago is on top of the Nobu Hotel called Nobu. I didn’t get the chance to check it out, but heard from local’s its the new spot to hang out! 


Chicago Bucket List:

  • Stay at a hotel with a view
  • Have Lunch on the Beach
  • Walk Down Michigan Avenue
  • Take a Chicago River Cruise
  • Visit Skydeck Chicago
  • Walk Through Millenium Park
  • Try Deep Dish Pizza
  • Check out Food Scene
  • Drinks on Rooftop Bar

Related Posts: 

Fun Chicago Travel Guide

23 Travel Essentials to Pack for Your Next Trip

Chicago Instagram Spots


Have you checked any of these off your Chicago Bucket List? 

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