36 Hours in Chicago: A Whirlwind Adventure

Even with just 36 hours in Chicago, you can have an incredible experience in the Windy City. We recently embarked on a quick trip to this iconic city, and despite the short timeframe, we packed in some amazing activities and unforgettable moments. Here’s how we made the most of our whirlwind adventure.

Arrival and Check-In

Our adventure began with a morning direct flight to Chicago. After landing, we hopped into a taxi and headed to the Cambria Hotel in the theater district. (For more info on the hotel, check out Cambria Hotel Chicago: The Perfect Stay for a Night at the Theatre.)

Luckily, we were able to check in early, which allowed us to drop off our bags and get started on exploring the city. Spending 36 hours in Chicago meant making every moment count, and we were off to a great start.

Pizza, Parks, and the Past

No trip to the Windy City is complete without deep-dish pizza. Our first stop was Giordano’s, and it did not disappoint. This was, without a doubt, the best pizza I’ve ever had.

Stuffed and happy, we walked to Millennium Park to see the iconic Cloud Gate, affectionately known as “The Bean.” Standing before this shimmering sculpture was a quintessential Chicago experience and a must-see when you have only 36 hours in Chicago.

Next on the agenda was the Chicago Crime Tour. This fascinating tour delved into the city’s notorious history, including tales of Al Capone and the Prohibition era. It was an intriguing way to explore Chicago’s darker side while learning about its past. Find out more: Secrets of Chicago’s Underworld: A Mob Tour Through History

Dinner and a Show

After the tour, we returned to the hotel to change for the evening. Dinner was at Petterino’s, a wonderful Italian restaurant. The food was delicious and set the tone for the highlight of our trip: seeing Les Misérables at the Cadillac Palace Theatre.

This beautiful venue enhanced the experience of watching my favorite musical, which was, as expected, phenomenal. Seeing a show like this is a perfect addition to any Chicago itinerary.

Morning in the Windy City

The next morning, we started the day with breakfast at the Corner Bakery Cafe. This spot is always a reliable choice for a hearty meal to fuel a busy day.

Energized, we embarked on the Chicago Architecture River Cruise—an absolute must-do in the city. This was my third time on the tour, and it never fails to captivate. The blend of fascinating narration and stunning views of the skyline is unmatched. Despite the chilly weather, it was a fantastic experience. Read my post for more info: Why I Can’t Get Enough of This Chicago Tour

After the cruise, we warmed up with hot chocolate at a nearby Starbucks before indulging in some souvenir shopping at Bye Bye Chicago. This fun shop had plenty of unique items to remember our trip.

Art and Departure

Our last stop was the Art Institute of Chicago. Wandering through its galleries and admiring its rich treasures was the perfect way to wrap up our visit. Read more: Unexpected Finds at the Chicago Art Institute

As our quick trip to Chicago came to an end, we headed back to the airport. While our flight was delayed for de-icing, it gave us a chance to witness the process, which was surprisingly fascinating.

36 Hours in Chicago: Final Thoughts

What started as a quick trip to see Les Misérables turned into a memorable mini-adventure. Chicago’s vibrant energy, iconic landmarks, and rich cultural offerings ensured that even in just 36 hours in Chicago, we left with lasting memories. So, if you’re debating whether a short trip to the Chi-town is worth it, the answer is a resounding yes!