Chicago in a Day


First time to the city? Returning on a tight schedule? Stopping by on a road trip? This city is the highlight of the Midwest in my opinion. Located right on Lake Michigan with the Chicago River running through it there are stunning views everywhere you walk. It’s a very clean city which is one of the reasons I like it so much.

You can come all year round. If you come at Christmastime you can see the snow-covered lake and Christmas lights. If you come in March you can see the Chicago River dyed green for St. Patrick’s Day. If you come in the summer you’re bound to have gorgeous weather for time at the beach. If you come in the fall you can see the changing colors of trees all around the city.

There are so many things to do here that it’s impossible to accomplish it all in a day. However, you can certainly pick and choose a few favorites. Check out some of my top sights in Chi-town.

Millennium Park

If someone knows anything about Chicago, it’s The Bean. This famous statue draws in almost 5 million visitors each year. While it’s fun all year round, it’s best in the summer and fall when there’s less chance of rain or snow so it’s cleaner. You can see the skyline reflected on its shell, and you can take cool pictures of yourself looking at it. However, the real magic happens when you walk under it!

Don’t miss the rest of the park like the faces on the fountains or the quiet grass areas. You can walk the park all the way out to Lake Michigan.


Navy Pier

The number one tourist attraction in Chicago is Navy Pier. With its shops, restaurants, movie theater, children’s museum, atrium & outdoor space, it’s no wonder. Its best charm is the Ferris Wheel. Ride it up for views of Lake Michigan and Chicago. Walk along the pier to the edge to get a better view of the lake, or even take a boat ride! It’s crowded, especially during peak tourist season in the summer, but its worth the hype. Stop here for lunch.

Michigan Avenue

Continue your walk down Michigan Avenue. There are tons of my favorite shops like Banana Republic, Ulta, Nordstrom, etc. You can see the Chicago Tribune headquarters, this beautiful old clocktower and cross over the Chicago River. In the distance you’ll notice you’re getting closer to the John Hancock building.


Water Tower Place

Located at the base of the John Hancock building is the Water Tower Place. This shopping center has glass elevators that you can ride up quite a few floors. I used to love coming here because of the American Girl Doll store. If you have children, you can take your dolls to lunch here. This is the best place for some shopping downtown, and its surrounded by both the Hershey Company and the Ghirardelli store. Stop in for a free sample of their chocolate!

One of the things I love most about this spot is the history. The Chicago Fire of 1871 was one of this city’s most horrific events in its history. The damages cost about $200 million according to National Geographic (over $1 billion today!) and it left the city in ruins. However, a select few buildings survived because they were made of limestone and did not burn in the fire. The Chicago Water Tower is one of them and has become a great symbol of the city. It used to be one of the tallest structures, but now its dwarfed by skyscrapers. However, it’s surrounded by a tiny park and is almost an oasis in this bustling city.


John Hancock Building

There are two iconic buildings in Chicago: The John Hancock Building and the Willis Tower (formerly known as the Sears Tower). I recommend the John Hancock Building. Both buildings are very similar in price (JH – $23, WT – $24) but with the John Hancock Building you’ll have the Willis Tower in your photos, which makes Chicago so recognizable. Because of John Hancock’s position on the northern end of the city and its 360 observation deck, you can see how expansive Chicago really is and get stunning views of Lake Michigan.


There are hundreds of great places to eat around Chicago, but for the purpose of this walking tour let’s go to Eataly next. Its a huge Italian market that has little restaurants dispersed throughout it. The wait staff is incredibly friendly and there are very classic dishes found on all of the menus. After you eat, head back downstairs and shop around the market more, and don’t forget about dessert! Grab a cannoli, gelato and other well-crafted desserts to have with a glass of Bellini.


Chicago Riverwalk

The Chicago River runs through this gorgeous city and is the perfect place to go after a big Italian meal. You can follow it up above and you can also take stairs down to the river and walk along designated sidewalks. It’s over a mile long and has a lot of places to sit and relax as the sun sets over the city. If you’re up for it you can take a river cruise too!


House of Blues

End the evening with a show. Located right on the Chicago River, the House of Blues is one of my favorite venues of all time. I’ve seen a handful of shows here. It’s compact and personal, and ending the evening with some live music never goes out of style. Check out their website for upcoming shows and times.

And that makes for one spectacular day in the Windy City!

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