My daughter Amily turned 18 this past weekend, and instead of buying her something she would forget about in a few weeks, I decided to give her a memory instead. She loves all things quirky and eclectic, so I wanted to take her to a big city full of lights, sounds, and all the other things that ignight your senses.
Neither of us had ever been to Chicago, and it's vibe was just what we were looking for. So, we hopped a quick flight from Birmingham, and we were taxiing into Midway Airport in little over an hour.
Follow us as we maximize our mini break in this vibrant and bustling metropolis nestled along the shores of Lake Michigan. From iconic landmarks to delicious deep-dish pizza and a touch of spooky history, our weekend in Chicago was jam packed full of adventure.
Day 1: Arrival & Navy Pier
I usually blame the penny-pinching on my husband, but the truth is, I'm pretty frugal myself, so forgoing a $40 airport taxi in favor of cheap public transportation was really a no brainer. To be honest, our family actually loves public transportation because it gives us a glimpse of local life. And, Chicagoans have certainly mastered the art of public transit.
We followed the clearly marked signs through the airport and down a few winding corridors lined with local children's artwork to the CTA (Chicago Transit Authority) train station that's literally connected to the airport. Midway is the start/end of the Orange Line, which is the only line there, so you can't really mess this up. We used the kiosk and bought two 3-day unlimited passes for $15 each. These were good not just for the ride from the airport, but for unlimited rides on all lines on the "L" trains, the subway, and busses for our entire trip. Trains run every 15 minutes and were downtown in about 25 minutes with zero traffic!
Our hotel, the Hampton Inn Chicago Downtown/North Loop was a great choice offering clean, comfortable rooms with an elegant art deco vibe in the lobby. It's location, just a block and a half from the State/Lake "L" station in the heart of the city, made it the perfect base for our explorations, and the complimentary breakfast was the cherry on top. The staff was very helpful and friendly, and I would definitely stay there again.
After we dropped our bags, we headed straight to Navy Pier on Lake Michigan's shoreline. Navy Pier was built between 1914 and 1916 as part of a larger initiative to provide docking and warehouse facilities for cargo ships and to serve as a training center for the U.S. Navy during World War I. At that time, it was known as "Municipal Pier. Today, Navy Pier is a bustling entertainment complex featuring a wide array of attractions, including restaurants, theaters, museums, shops, and the iconic ferris wheel the Centennial Wheel.
And speaking of ferris wheel, did you know that the first ferris wheel was the Chicago Wheel that was featured at the 1893 World's Colombian Exposition Chicago? It was a groundbreaking engineering marvel for it's time, and each of it's 36 cars were capable of holding a whopping sixty people. That's a ridiculous 2,160 people at full capacity. The Centennial is significantly smaller, but still offers stunning views of the city's skyline and Lake Michigan.
After our ride on the Centennial, we ate dinner at Giordano's, a Chicago institution known for its legendary stuffed deep-dish pizza. It was our first time experiencing Chicago style pizza, and we embarassed ourselves with the amount of food we devoured. Chicago wished Amily a happy birthday with the last fireworks show of the summer season, and we hit the pillows hard after a perfect 18th birthday.
Day 2: Exploring the Loop and Haunted History
Our second day began with a guided tour called "The Loop and Millennium Park." Did you know that most major cities have companies that offer free tours? Yes! They are "pay what you like" tours and the guides work strictly on tips, although you do have to sign up for the tour in advance. We selected a tour by Free Tours By Foot. Our guide was Mike and he's lived in Chicago for the past 46 years. We learned so many interesting details about Chicago from him, and it was clear he loved his city. As we made our way through the streets, he pointed out hidden features and told us about the city's fascinating history including facts about the Great Fire of 1871 and rapid post-fire reconstruction, Millennium Park and the Cloud Gate sculpture (more commonly known as "The Bean") and so many other interesting features. We even learned that the nickname for Chicago, the "Windy City, isn't because of how windy the city is. It's actually not any more windy than many other cities in America. After the Great Fire, the city rebuilt an ultra modern city at record speed. It's leaders wanted to show it off by hosting the 1893 Expo. Politicians in Washington were so sick of all the bragging, they called Chicago a city full of hot air and wind...The Windy City!
We headed back to our hotel to let our brains decompress from all that knowledge we soaked in on our tour. After a good veg-out, we uncrossed our eyes and embarked on the spine-tingling "Haunted History" tour, exploring Chicago's darker side. This was another Free Tours by Foot by tour guide Kelli, a historian, researcher, and amazing storyteller. She scared the pants off us with tales of psychopaths, unsolved mysteries, and the eerie occurrences that have left their mark on the city. The experience added a unique dimension to our trip.
Day 3: Skydeck, Chinatown, and Art Institute of Chicago
Our final day in Chicago was packed full of experiences that highlighted the city's cultural richness. We started bright and early with an 8 AM visit to the Skydeck at the Willis Tower. Formerly known as the Sears Tower, the Willis Tower was completed in 1973 and stood as the world's tallest building until 1998. Today, it is an iconic skyscraper that offers breathtaking views from its famous glass-floored observation deck. The experience was thrilling and slightly nerve-wracking, but the views were definitely worth it.
After the Skydeck, we hopped the Redline south to venture into Chicago's energetic Chinatown where we strolled through streets steaming with flavors of Bao Buns and dumplings. We enjoyed exploring the colorful streets, authentic markets, restaurants, and unique shops.
Our last excursion was the Art Institute of Chicago, where we were lucky enough to score tickets for the special exhibit Van Gogh and the Avant-Garde: The Modern Landscape on its last day at the museum. The Institute is home to one of the most extensive and impressive art collections in the world. It boasts over 300,000 works of art, spanning thousands of years and encompassing diverse cultures and artistic movements. It's no wonder we spent almost four hours admiring masterpieces by Picasso, Matisse, Monet, and other world renowned artists.
Our three-day weekend in Chicago was loaded with fascinating facts, interesting culture, and mouthwatering cuisine. From the heights of the Skydeck to the depths of the city's haunted history, we had an incredible time in this magnificent Windy City. But most importantly, our Chicago style mini break was a great experience for me and my daughter to just spend time together making memories that will last us a lifetime.
Interested in taking your own Chicago style mini break? Let Bound Bookings take care of all the details. Contact us at BoundBookings@gmail.com for a custom quote today or visit www.boundbookings.com.
About the Author:
Christina Dickens is a passionate traveler and writer who believes that exploring the world should be accessible to everyone. With a keen eye for budget-friendly destinations, she aims to inspire fellow travelers to embark on unforgettable adventures without compromising on quality. As the owner of Bound Bookings, Christina is dedicated to helping budget-conscious travelers create exciting and memorable experiences.
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