15 Bucket List Chicago Activities

Hello readers and friends! If you’ve clicked on this blog I am assuming you’d love to hear all about the exciting adventures that await you when visiting the windy city, or you're just nosy. Well either way I hope you enjoy these top bucket list Chicago items along with some of my favorite photographs that we took while visiting the beautiful city. If you’d like to know more information about the city and other tourist information refer to our complete Chicago Travel Guide. Without further ado, let us jump into our blog. 

1. Sky Deck- This destination was definitely one of the first places that popped up in my head when writing this blog. The sky deck is a museum and deck experience located in the tallest tower in Chicago, on the 103rd floor to be exact. You can take amazing glass box photos, shop in their gift shop, and catch an amazing view of the entire city. A must try activity as long as you are okay with heights!

2. Logan Square- I know I am a little bias because I called this awesome little community within Chicago home for five weeks, but I really do think this neighborhood is a must see if you're touring the area. This community is a combination of unique local businesses and super fun diverse restaurants all located just a ten minute transit outside of the city. Spend the day exploring this super safe area and grab an awesome meal and movie.

3. Chicago based food- The food scene in Chicago is absolutely wild and delectable. When visiting you have to try some of their famous or original dishes like Chicago deep dish, Portillos or visit some of their compilation food halls like revival food halls. You will never run out of food options within this city!

4. Clark Street- Located about one block off of the riverwalk this super popular street offers a lively restaurant, bar, and club scene. With a plethora of activities to enjoy make sure to make reservations since everything is so competitive since the pandemic. Some awesome options located around the area include The Joy District, The Untitled Supper Club, Howl at the Moon, and The Smith.

5. Fulton Market District-Another really interesting neighborhood located just a quick transit train away from the riverwalk, similar to Logan Square, is the Fulton Market District. This community has quickly turned into a fun and hip place for people to visit after work and for the younger twenty-somethings in the area. Come try out their bars and restaurants, and while your visiting check out their awesome graffiti murals.

6. Live Music Bar- Every corner you turn while your visiting you’ll find a beautiful rhythm filling the streets with a diverse sound. Chicago has an amazing music scene all happening in a lot of bar establishments like Jazz Clubs, Piano Bars (Howl at The Moon), and Band bars.

7. Cloud Gate and Park- This infamous monument is a must see when traveling to Chicago along with the beautiful park that surrounds it. Cloud Gate, also known as the bean, is a huge art marvel that provides great insta-worthy shots and you can also touch it which I enjoyed. Spend an afternoon checking out the entire park and the other monuments that reside here.

8. Ride Transit- While in the City, one of my biggest recommendations when transporting is to take their awesome transit train systems. You get some kick-ass views of the city while exploring the neighborhoods, and the transit is also very inexpensive, making it a must try when visiting.

9. Baseball Game- We all know of the lifelong debate between Cubs or White Soxs fans but when in the city it's a must to at least go to one of the stadiums! We visited the Cub's stadium and it was super amazing to see so much history within a building but I was also super impressed with how great the updates looked while touring the building. Grab a hot dog and beer to cheer on your favorite team.

10. Speakeasy- One of the really interesting history lessons of Chicago is they have a long history of mafia and gang violence throughout the city. Due to this when the prohibition happened, Chicagos' bar scene pretty much continued to thrive through the speakeasy industry and some of them still operate today. These secretive and intimate bars are an amazing way to relax and enjoy a different part of Chicago's history.

11. Riverwalk- The famous riverwalk was by far my favorite place to stroll and relax around every time I was exploring the city. Centrally located in the middle of the city and on the river, the entire walk is a dream compilation of the best city, water, and people watching views. There are a ton of different sitting areas, restaurants, and bars located on the walk as well. I highly suggest spending a day getting lost and enjoying the entire river, bridges, and city.

12. Palmer House- This absolutely gorgeous building was originally built for the world fair, and after 3 different models, the Palmer house stands as a true time testament for the city. The beautifully painted ceilings, gold decorating, and a secretive haunted past make for an interesting story and leaving you feeling like royalty. Make sure to grab a drink and a picture when visiting.

13. Chicago Theatre- The Chicago Theatre is one of those monuments that you have to at least walk by and take a quick picture of because the lit up sign is so iconic. If you have the opportunity I highly suggest seeing a show or play within this arena, you won’t regret it!

14. Navy Pier- Very similar to most piers, this water surrounded tourist area offers a plethora of family like activities for people to visit. The pier offers carnival rides, a huge Ferris wheel, restaurants, bike tours, and shopping. There are also a ton of boating adventures offered off this pier if you’d like to explore the water as well.

15. Walking Tour- Last but certainly not least, a great bucket list item is to take one of the super awesome walking tours available here! Walking Tours are an amazing way of learning a ton about the city, exploring the different streets, seeing amazing architecture, and getting your steps in! I have done a free walking tour here and a ‘ghost and gangsters’ tour and both were so much fun and knowledgeable. There is honestly no better way to learn fun facts about the city. 

And there you have it folks, my complete bucket list for the City of Chicago! I hope this inspires you to book that plane ticket out to the city or if you already live around the area to try something new. If you’d like to see more amazing photography from Chicago check out our Chicago Photography blog here. If not we hope you have a fabulous day and we'll see you on our next blog! 

Stay Safe and Happy Travels! 

OnBrand