Chicago, Illinois… The 3rd largest city in the US with an estimated 2.7 million residents within it’s 234 square miles! Being home to 2 MLB teams, an NFL, NHL, and MLS team, iconic foods like the Chicago Dog and Deep Dish Pizza, and sites like Willis Tower and Cloud Gate (The Bean), we knew that we couldn’t visit Illinois without making a stop in the Windy City! Just like many of our itineraries, our time in Chicago was short, sweet, and packed full of activities, so hang onto your seat and we’ll show you how we made the most of our one day in Chicago!
*Check out our "Chicago for a Day" vlog for a closer look at our time in the Windy City!*
Let's get into it!
If you’re like us, then you need caffeine (and sometimes sugar) to get the day started! There are tons of great coffee and breakfast spots to choose from in Chicago, but here are a few suggestions to get you started. We normally try to stick to local spots when we visit places, but Natalie loves Nutella, plus, it's super close to Millennium Park/Cloud Gate (AKA The Bean) which is where we wanted to hang out while we ate our breakfast and drank our coffee.
9:00 am: Coffee/Breakfast
Nutella Cafe (where we went)
Dollop Coffee Co.
Sawada Coffee
After a relaxing start to the day, it’s time to check out some of Chicago’s amazing parks!
10:00 am: Explore Parks
Millenium Park
Maggie Daley Park
Lakefront Park
Buckingham Fountain
Grant Park
Now that you’ve worked up an appetite after walking through the beautiful green spaces, it’s time to get a taste of Chicago for lunch!
12:00 pm: Lunch
Portillo’s/Barnelli’s (where we went)
Gene & Jude’s Red Hot Stand
Superdawg Drive-In
Fatso’s Last Stand
Chicago’s Dog House
Before our visit, we asked multiple friends that lived in Chicago for their “must-do” activities in the city, and all of them said that we HAD to do the Architectural Cruise, and we must say… It was totally worth it!
1:30 pm: Architectural Cruise with Shoreline Sightseeing
This 75 minute tour takes you on all three branches of the historic Chicago River past dozens of landmark buildings all while the docents entertain you with the stories behind the Chicago landmarks.
No trip to Chicago (especially if it’s your first time) would be complete without a stroll down the Magnificent Mile! Being home to one of only six Starbucks Reserve Roasteries in the world and offering more high end shopping than even a Kardashian could dream of, you won’t be disappointed!
3:00 pm: Explore the Magnificent Mile
Starbucks Reserve Roastery
Zara
Saint Laurent
Saks Fifth Avenue
Bloomingdale's
Neiman Marcus
Prada
Gucci
Jimmy Choo
Louis Vuitton
Christian Louboutin
Tiffany & Co.
If there’s one thing that there’s no lack of in Chicago, it’s rooftop bars with amazing views! And we’ve put together a list of some of the best ones in the city!
5:30 pm: Happy Hour with a view
The Signature Lounge at the 96th
Rooftop at Nobu Hotel
Kennedy Rooftop
Cindy’s Rooftop
London House
Before ending your time in the Windy City, you HAVE to have some Chicago Deep Dish Pizza! No matter which side of the pizza spectrum you stand on (New York or Chicago), you can’t deny that there’s something special about the delicious, buttery crust on a classic deep dish!
7:30 pm: Dinner
Lou Malnati's (where we went)
Giordano's
Gino’s East
And just like that, our time in Chicago has come to an end! Of course there are SO many more things to do and sites to see in this amazing city, like Willis Tower, Navy Pier, Wrigley Field, Chicago Riverwalk, Lincoln Park Zoo, and much more, but there are only so many hours in a day! That said... We hope that this itinerary helps you in planning your next trip to the Windy City!