The Ultimate One Day Chicago Itinerary



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!