The Wondrous Sights of the Windy City

Chicago is a top tier city with a reputation that far exceeds itself for a reason. Currently the third biggest city in the US, this mid-west city has a ton of great landmarks and attractions to keep you busy for a long time. Plus all the music, culture, great food, and history made it particularly difficult to choose what made the list. Here’s the long awaited bucket list tour of the Second City. Enjoy!

#10 Visit the Navy Pier

Can’t be a big city without your very own giant Ferris wheel. Find restaurants, rides, and lots more to do at the Navy Pier right off Lake Michigan. With so many events going on its better to check this site so you can decide what to do for yourself. For your own sake I hope you’re reading this in any other season besides winter.

#9 River Boat Architecture Tour

While you’re down at the Navy Pier, might as well check out the highest rated tour of Chicago, Shoreline’s Architecture River Tours. This takes you right through the center of downtown to view some of the most astounding Sky scrapers I’ve ever seen. With lots of history of the Chicago fire and the engineering of the architectural designs, I was actually amazed on how entertaining it was. Absolutely would recommend. Just gazing into that emerald blue water is reason enough.

#8 Buckingham Fountain

Pretty much self explanatory. Just a super big fountain, but still pretty cool to look at. It pays homage to London’s royal palace of the same name. Right in the center of Grant park, it’s definitely a timid detour from the fast paced downtown scene. For all my budget travelers out there, this one is free.

#7 The Second City Comedy Club

This iconic comedy club is known for its famous alumni celebrities. Some of its greatest include, Steve Carell, Stephen Colbert, Chris Farley, Tina Fey, Bill Murray, Mike Myers, and Amy Poehler. It’s a training school for new comics and is guaranteed to provide laughs all night long. Just get your ticket early and don’t sit too close to the front.

#6 Walk the Magnificent Mile

I don’t usually promote walking as a favorite activity of mine, but there’s a few spots to hit on the walk uptown. Basically just a street with lots of high end shopping and fancy restaurants, but the energy from the crowd is a cool experience. At the North-end of Michigan Ave is the Old water tower, which is the last remaining relic before the infamous Chicago Fire. Interesting to see how the old architecture contrasts with the newer surroundings.

#5 Check out the World Class Museums

Chicago is a city flowing with artistic ingenuity, which is present in all of its museums as well. The Art Institute of Chicago, The Field Museum, and the Adler Planetarium are just a few of the great places to spend an entire afternoon. I could make an entire post about all the content held within so I’ll just post some pics. *BONUS* The view of the Chicago Skyline from outside the Planetarium is incredible and worth the visit in itself.

#4 360 Chicago Observation Deck

The best way to experience a city is to view it from high up. This Observatory at the John Hancock Tower offers an amazing view of Chicago from all cardinal directions. And if you’re in the mood for some thrills, purchase a ticket for the Tilt, which places you almost completely horizontal to the ground below. Not for the faint of heart.

#3 Eat a Deep Dish Pizza

Being a self proclaimed food expert means there had to be at least one food experience on this list. Chicago is known for its delicious selections of food and as a lover of pizza, that deep dish style was the priority. And it definitely lived up to its hype. After trying multiple places from a variety of sources and witnessing altercations over the best place (people are serious about their favorite pizza joint), I think Giordanos was the best with Lou Malnati’s as a close second. If your into pizza, then this is definitely a trip you want to make. Some other honorable food mentions (might make a separate post just on all the food) include Chicago style hot dogs, Italian beef sandwiches, and Hannah’s Bretzel for one of the most flavorful sandwiches in the world (maybe top 5).

#2 Willis Tower Sky Deck

I know there was already an observation deck on this list, but the Chicago Skyline is worth seeing from a few different perspectives. My suggestion would be to do one in the afternoon and one at night for a completely different vibe of the city. Formerly known as the Sears tower, This is the tallest building in Chicago and was the tallest in the world at one point. Standing over the Sky ledge is a frightful feat but offers an experience like no other. Become a Part of the Elite 103!

#1 Cloud Gate at Millennium Park

The well deserved top spot of Chicago belongs to the esoteric Cloud Gate AKA the Bean. It might just be my affinity for reflective objects but the optical illusions it offers can lead to some very creative pictures. There’s always something going on in Millennium park so there’s never a shortage of options. Concerts, Rock climbing, or gardens make it easy for time to just pass by. No trip to Chicago is complete without a stop here.

Chicago is a very underrated city and I hope everyone gets to experience it at least once in their lives. If you’re thinking about the best time to go, I would recommend the Fourth of July. Great weather, tons of free concerts, and the famous Taste of Chicago food festival. As always thanks for reading and Keep Leveling up.

*Bonus* I made a video of some of the cool stuff around the city. Part 2 also below!