C H I C A G O: 10 Things To Do


Summer in Chicago is simply perfect.

Now that it’s officially summer, I highly recommend a visit to this great city while it’s still warm!  I finally took my first trip to Chicago last year (2017) during the July 4th weekend and I had a blast!

I can honestly say I was a Chicago lover prior to visiting, I mean I’ve only heard great things about this city.  However, my interest in Chi-town mostly stemmed from my celebrity crush on Common, who is born and raised in the Windy City.

So I finally made it! When your good friend tells you she’ll be in Chicago for the summer and to come visit, I obviously agreed.  I try to take advantage of long weekends to get out and travel somewhere new whenever possible and this was definitely on my list for a long time.  

Below are my suggestions of things we did as tourists over a long weekend.  Heads up, you’ll be doing a lot of walking so bring your comfy sneakers.

#1. Explore Streeterville / Downtown

When you’re short on time and looking to explore a location that has it all, the Streeterville area is a great place to start!  You’ll get many tourist attractions within walking distance of this little neighborhood, including, the Chicago River, Lake Michigan, and the Magnificent Mile portion of Michigan Avenue for some great shopping.

Streeterville is also home to Chicago’s tallest skyscrapers, like the John Hancock Center, and has some of the best rooftop views in the city (see below)! Be sure to stop by the 96th Signature Lounge and the 360 degree observation deck in the John Hancock building.  For more daring travelers, check out the TILT, an enclosed moving platform that literally tilts you out 1,000 feet over Michigan Avenue from the 94th Floor of the John Hancock building.

Rooftop views from Streeterville

#2. Chicago Riverwalk

This was such a cute stroll (1.25 miles) along the Chicago River with shops and restaurants at every step.  You can hop on a boat tour, grab some ice cream, or hangout out with friends at the Island Party Hut, an island paradise on the west end of the river that offers outdoor games, live music, and casual eats. More on the Chicago Riverwalk here.  Also, the Architecture Tour on the Chicago River is a must!

Photo Jul 02, 10 15 15 AM (1)
Chicago River

Photo Jul 03, 2 19 52 PM

Did you Know: The Chicago River is dyed green every year just in time for the annual St. Patricks Day Parade.

#3. The Ledge at Skydeck Chicago

A popular tourist attraction, no trip to Chi-town is complete without a stop at the historic Willis Tower, the tallest building in the Western Hemisphere, and The Ledge at Skydeck Chicago!  Head up to the 103rd floor of Willis Tower for crazy 360-degree views of the city and beyond and if you’re brave enough, you can also step out on The Ledge, a glass balcony that extends over 4 feet outside of the building, for a unique and exciting experience! Don’t look down if you have a fear of heights and be prepared for long lines! The view from the top is worth it.

Photo Jul 04, 10 40 10 AM
The Ledge at Skydeck Chicago

Photo Jul 04, 10 43 18 AM

#4. Cloud Gate & Millennium Park

Everyone who visits Chicago make’s their way to “The Bean,” formally known as Cloud Gate. You won’t miss this stainless steel sculpture in Millennium Park that reflects the Chicago skyline and the clouds above, hence the name “Cloud Gate.”

Photo Jul 05, 6 56 17 PM


#5. Navy Pier

If you’re in Chicago on July 4th, make sure you check out the fireworks at Navy Pier, another iconic landmark in the city.  Luckily, my friends apartment overlooked the pier and we had great views of the fireworks show. For weekly events at the pier, check out navypier.org.

Morning Views of Navy Pier

#6. Lincoln Park and the Northside

In an attempt to explore another neighborhood nearby we traveled just north of downtown Chicago to an area called Lincoln Park.  This area has beautiful upscale homes, lot’s of history, and great eats.  Lincoln Park sits along Lake Michigan and is home to Chicago’s largest park (Lincoln Park), the Chicago History Museum, Lincoln Park Zoo, DePaul Art Museum, and more.  On our walking tour of the Northside of Chicago we came across the historic Wrigley Field, the second oldest baseball stadium and home of the Chicago Cubs, and enjoyed a tasty BBQ lunch at Sheffield’s Wine & Beer Garden.

#7.  Lake Michigan Waterfront / “The Beach”

Coming from Los Angeles where we have actual beaches, I chuckled when I found out that locals refer to Lake Michigan’s waterfront as “The Beach.”  I mean parts have sand and everything and families are out swimming and having a blast so I guess I can’t be mad at them for making the most of what they got!  Either way, you’ll probably end up at the waterfront on a nice summer day, so take a stroll or jump in!

“The Beach” / Lake Michigan

#8. Chicago Style Pizza

While the best deep-dish pizza in Chicago still remains highly debatable among locals, as a visitor you have to go to at least one of the many pizzerias for an authentic slice of Chicago pizza. TimeOut put out a recent list of their favorite deep-dish options here.

After consulting with friends native to the area, we ended up trying Lou Malnati’s Pizzeria for my first authentic experience.  Disclaimer, I’m not big on pizza so I don’t claim to be a pizza connoisseur but I thought Lou Malnati’s was just O.K.  Honestly, I prefer my mama’s pizza better or maybe deep dish just isn’t my thing.  Giordano’s is another pizzeria that kept coming up as one of the top competitors for the best deep-dish pizza in Chicago.  Regardless of my personal taste and the numerous options, you have to try at least one pizzeria if you’re visiting the city or else you’ll regret it.

#9. Andy’s Jazz Club & Restaurant

My friend and I are pretty laid back and both love live jazz. We came across Andy’s Jazz Club and enjoyed a night out.  While we didn’t eat there, the food sounded so tasty given it was a southern/creole flare, one of my favorite cuisines.


#10. Caffe Umbria

For the best coffee in the downtown area check out Caffe Umbria!  The iced vanilla latte was absolutely delicious and perfect on a hot summer day.  As an added bonus, this authentic cafe is based out of my hometown of  Seattle, Washington! No wonder why I love it so much!  


And there you have it, a fun-filled July 4th weekend in the Windy City! What are your favorite things to see and do in Chicago in the summer?  Another trip is definitely in order.




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