Chicago Bucket List

Chicago Bucket List

With an endless list of things to do in Chicago, you’ll probably start to wonder if it’s possible to get through all of it in just a few days. Truth is, probably not. However, for your convenience, I have summed up a bucket list to help you get through the best of the best for your stay in one of America’s largest cities, Chicago!


1. Take a helicopter ride

Nothing beats seeing the city from the sky. If you’re not afraid of heights, do it. If you are afraid of heights, then you should still do it. The views of Lake Michigan, Millennium Park, skyscrapers, Grant park… you’ll thank me later.

2. Visit the Buckingham Fountain

One of the world’s largest fountains and a landmark of Chicago you cannot miss! I recommend seeing it by night when it’s all lit up in lights.

3. Take a selfie at Cloud Gate

Also known as “The Bean,” it is an enormous sculpture that will instantly make you want to snap a photo of yourself with it! Walk around it and underneath it, so you can fully see all the different perspectives it gives you from your reflecting image.

4. Go on the ledge at SkyDeck

My favorite spot to go to every time I visit Chicago! Located in the Willis Tower, make your way up to the 103rd floor for amazing panoramic views of the city and dare to step out on the ledge. Snap photos of yourself standing, sitting, or laying down on it- it’s sure to give you a quick adrenaline rush!


5. Enjoy a boat ride on Lake Michigan

Book a quick cruise for a ride on Lake Michigan, or even an architectural boat tour on the Chicago River. You’ll be impressed with the city’s skyline from afar.

6. Eat a deep dish pizza slice

One simply CANNOT leave the birthplace of deep dish pizza without trying a deep dish slice of deliciousness yourself! I recommend going to Pizzeria Uno, where it was originally invented.

7. Stroll along the Magnificent Mile

Get ready to shop until you drop, ladies and gents! Or… you could just window shop all along N. Michigan’s 13 blocks full of departments, hotels, and restaurants. Either way, it is definitely a magnificent mile you must experience.

8. Visit the Art Institute of Chicago

Known to be one of the United States’ largest and oldest art museums ever, you’ll be sure to spend a good few hours here exploring exhibit after exhibit. Book your tickets in advance or arrive early in the morning when it opens, so you don’t get caught waiting in line for too long.


9. Sweet it up at Rainbow Cone

Ice cream lovers or not… You. Will. Love. This. Place. Just go…now.

10. Tilt over the city at 360 Chicago

Another amazing skyscraper, John Hancock Center, offering to actually TILT you over Michigan Avenue at a 30° angle. And don’t worry, it’s 100% safe and pure of adrenaline rush.

11. Take a photo op at Big Monster Toys

If you find yourself near 21 S. Racine Avenue, then stop for a really quick photo in front of a humongous, monster door! Think I’m crazy? Then check this out.

12. Watch a game at Wrigley Field

Home to the great Chicago Cubs, book a tour or stay for a game if you happen to be in town while it’s baseball season.


13. Hang out at Millennium Park

Or Grant Park! Both parks are basically right next to each other, so take a couple hours out of your busy day to relax, stroll around, have a picnic, or simply people watch. Makes for a perfect day break!

14. Be a kid at Navy Pier

Navy Pier will surely bring out the kid in every single one of you! Ride the ferris wheel, souvenir shop, dine, and the best part… stay for the incredible fireworks in the evening.

15. Catch a show at the Chicago Theatre

A landmark in Chicago you’ll want to visit! Check in advance (here) for any special events that will take place while you’re there.

16. Stargaze at the Adler Planetarium

If you love anything to do with space, then this spot’s for you! Being America’s first planetarium to ever open, you’ll wind up leaving impressed after checking out a couple of exhibits.


17. Eat lunch at Toppers Pizza

Toppers Pizza is not your ordinary pizzeria. Plan to have your lunch or dinner here and you won’t regret it! My favorite is the Loaded Tot-zza….pizza with tater tots! Crazy good!!

And if you’re 21 years of age…

18. Grab a few beers at Beermiscuous

If you love beer like I do, then this is the place for YOU. With over 300 selections of craft beer, you can mix and match your favorites for a good price. Bring along a meal or a snack, friends or a laptop (free wifi) and hang out! Here’s their beer menu you can check out before you head over.

And if you’re really up for it…

19. Attend Lollapalooza

One of the greatest music festivals ever takes place right in Chicago’s Grant Park every summer! If you can make a trip here over the summer, try to make it on time for Lollapalooza! You can read all about Lollapalooza right here!


What else would you add to this bucket list?

3 thoughts on “Chicago Bucket List

    1. Thank you so much, Jackie! I truly appreciate it 🙂 I’m sure you’ll visit Chicago someday too! I just followed your blog, it’s so cool that you’ve been to so many countries already!!!! Such an inspiration ❤️


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