Welcome to the Windy City! | 10 Attractions in Chicago, Illinois

Welcome to the Windy City!

view from a hotel in Chicago

My first visit to Chicago, Illinois involved, like a lot of my early trips, a band bus. My high school band played in the annual Thanksgiving parade in Chicago so we headed up in chilly November to participate. Despite being in the city for the better part of a week, I barely remember much about the city. I have vague memories of pizza (tragic considering how great pizza is in Chi-town) and vivid memories of freezing my ass off. I definitely remember having numb toes before I finished marching in the parade.

Needless to say, I had to revisit Chicago–if only so I could actually experience the city.

What to See and Do

Um, how do I jam two days’ worth of WOW into a post? Chicago has so much going on that I’m sad I didn’t get to do everything. From the moment the plane touched down I bounced from site to site, event to event, park to park.

Honestly, I could have wandered around downtown everyday, all day and not felt I wasted my trip. Chicago exudes beauty I wasn’t prepared for.

But, for the purposes of my post, how about I break this whirlwind–literally! hold onto your hats–down into ten attractions to check out in Chicago, Illinois:

1. The Views

View from Hancock Center in Chicago
Can you believe I’m standing in the girls’ bathroom at the John Hancock center?? Beautiful views…

Because seriously, this city is made for views. Hotel views, Willis Tower views, city street views, river front views… Views as far as the eye can see. People come far and wide for the views. In fact, I noticed the view in the Lyft ride from the airport and stared as if star struck. The city slowly opened as the day drifted from early morning into afternoon. I kept waiting for the awe to wear off, but every time I stared outside my hotel window, the view struck me all over again. I felt like a school-girl with a crush, giddy at the sight of high rises. Chicago truly has one of the best skylines in the country (and I say that as a woman who loves a good skyline).

For a fantastic (and free) view? Ride up to the 96th floor of the John Hancock Center and look out. Get a little fancy and if you have some cash, buy a drink while you’re there!

2. Walk through Downtown…

Downtown Chicago

For fun, for exercise, for the view, for the FOOD! Downtown has so many twists and turns, loops and lifts, so many sections that you would almost swear you were in a new city. From the Magnificent Mile (more on that below!) to one of the many parks, or even the theater district. I’d walk a few blocks with restaurants on every corner, then I’d turn and suddenly I’m in a shopping district. I spent every morning walking through downtown. Walking or riding through the Loop (the business district) will have you craning your head up just to take in the sights. You’re never quite alone on those city streets, no matter what time of day or night.

3. Magnificent Mile

shops downtown Chicago

SHOPPING!! And for those with money to spend, or a credit card to burn, this strip will call your name all day. Magnificent Mile holds several high-end stores and boutiques. The strip also has some more reasonably prices stores glamored up in bright lights and large signs. The John Hancock Center is right at the northern tip of the strip. Personally, I enjoyed the views along this “mile” the most… Don’t want to spend that kind of cash? Don’t worry, a few blocks in the opposite direction you’ll find more shopping for the budget conscious spender (like myself!)

4. Chicago Theater

Chicago Theater

Truthfully, I walked down this street just for a shot of the iconic theater. I wanted to break into song and dance–” and all…that…JAAAAAAAAAAAAAAAZZ!” I didn’t to go in, but the theater is still active; if you’re in the area, don’t hesitate to check out a play or performance.

5. A Walk Through the Park

Jay Pritzker Pavilion in Millennium Park
Jay Pritzker Pavilion in Millennium Park

Just pick one! Chicago has so many parks there’s no way to visit them all in a day. Grant Park, Lincoln Park, and of course the famous Millennium Park. The latter features Cloud Gate, which I get more into next! I booked a hotel right in front of Millennium Park and a short walk from Grant Park so I wandered through both every morning. Best to visit parks in the golden hour before tourists and visitors crowd around. Especially if you just want to enjoy the peace.

6. Cloud Gate

Cloud Gate in Chicago

Or the Bean as it’s more affectionately called. And really, you can obviously see why. The iconic attraction literally looks like a giant, silver bean. If you do nothing else in Chicago, you must do this very touristy, very ‘Gram-worthy visit. You must take your photo with the Bean and post it to social media. Trust me, you have to. It’s akin to walking in Times Square or eating a beignet at Café Du Monde. You haven’t really visited Chicago if you don’t do this. I wouldn’t recommend touching the Bean though…

woman standing in front of Cloud Gate in Chicago
my touristy photo in front of the Bean

As previously recommended, get up early to get the best shots of Cloud Gate–any later than 9am and you’ll have hundreds of people in your selfie.

7. Chicago Riverwalk

RiverWalk ChicagoSeems every city I visit has a river walk, right? Well Chicago is no different. The new renovated riverwalk spans about 9 blocks down the Chicago River and features restaurants, boat tours, shops, and even kayaking! The vivid color of the Chicago River struck me–only on gulf-water beaches do I normally see such a mixture of aquamarine. And this isn’t the ocean; the Chicago River merges into Lake Michigan. With beautiful views of the city in every direction, walking or riding along the river is a must when visiting downtown. Speaking of beautiful views…

7. Architectural Boat Tours

boat tour along the Chicago RiverOkay, so I know I told you that you must visit Cloud Gate and take a picture, but if you have time for two things, you must do a boat tour of the skyline. In fact, make time for two things and take the tour. Literally the absolute best thing I did while I traveled in the Windy City. The knowledge of the buildings aside, riding along the river felt so peaceful after a full day of running around the city. Chicago has several different boats that offer a variety of tours. I took the twilight tour and loved it! My only recommendation? If you visit anytime after August, bring a jacket…hell, bring a coat! You’ll thank me later.

8. Navy Pier

Centennial Wheel at Navy Pier in Chicago
Centennial Wheel at the Navy Pier

My only regret? I didn’t visit Navy Pier in the daylight. Not quite a fair or carnival, Navy Pier has local shops and restaurants to choose from. Of course, being a pier, a few boat tours also dock here–the view of the Chicago skyline from the pier will take your breath away! Not to mention the iconic Centennial Wheel! And of course I rode the Ferris Wheel…you know I can’t resist. Navy Pier also features exhibits and events throughout the year for locals and tourists alike.

9. I’ll Take the Deep Dish Please… FOOD!

deep dish pizza in Chicago
from Giordano’s

Before my visit to Chicago, I would not have guessed the city had so many different flavors to choose from. Vegan, Vietnamese, sweets, and of course, their famous deep dish pizza! I truly dined on some of the best food of my travels in this beautiful city…can’t wait to take you on a food tour of Chicago!

10. Climb Sears Tower (or Willis Tower)

views from Sears Tower in ChicagoFormerly the tallest building in the world–not to mention formerly known as Sears Tower–the [now] Willis Tower remains the tallest building in the city. And yes, holds some pretty spectacular views of the entire city from over 100 stories up. If you can stand waiting in line to ride up the elevator until your ears pop…and then waiting in crowds to get a clear shot of the glass…and then waiting in line to get your chance at the skydeck, then you should check out Sears Tower.

(though I still maintain you should go to Hancock Center–cheaper, equal views, and you get to grab a drink!)


I wanted to visit Lincoln Park, Logan Square, but I didn’t get the chance to make it up that way. I wanted to sample burgers from Au Cheval but never made west of the Loop. I really wished I had made it for Lollapalooza just so I could say I’ve been! But, if you do head to Chicago, I would also recommend walking through the Pedway system under the city streets!


Did I forget one of your favorite places? Tell me where I should go on my next visit!


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