From Chicago, With Love – A Day Trip to the Windy City

One of the best things about living in central Michigan is how easy it is to pop over to Chicago. If you ever find yourself bored and yearning for some good food, city views, and great vibes, you can easily grab a cheap 3hr train or bus to Chicago. My husband and I found ourselves bored, hungry and in need of some good vibes this past week, so on a random Tuesday, off to Chicago we went! Arriving at 6am via bus and leaving at 6pm via train, we spent a beautiful fall day roaming the streets of Chicago.

Known as the Windy City, or Chi-town to the locals, Chicago is one of the largest and most diverse, cities in the Midwest United States. My favorite time to visit Chicago is in the early fall – the weather is just right for strolling around the city. Whether you are in Chicago for a day or a weekend here are some hot spots to add to your itinerary.

See “The Bean” at Sunrise

Did you know that the iconic “bean” in Millennium Park is actually called the The Cloud Gate? Although there are many art works in Millennium Park, The Cloud Gate has become the most famous. It’s reflective surface creates a beautiful mirror image of the city skyline as well as a trippy reflection of oneself when walking around and under it. While the bean is beautiful at all times of the day, sunrise is the best time to visit. The sun reflecting off of the bean makes the mirror image of the city skyline glow and shine. It really is a site to see! Also, you can see the entire mirror image clearly without it being speckled with people. When you finish admiring the bean be sure to explore the rest of the park! We checked out the other art installations and architecture.

Walk the Lakefront Trail

Chicago sits on Lake Michigan, which is one of the United State’s five great lakes. It’s close proximity to the lake is the reason that the city gets below freezing temperatures in the winter and strong winds in the spring and fall. When the lake is not causing whirlwind weather, it is very beautiful to look at! The Lakefront Trail is the perfect place to walk and talk or even have a seat and enjoy a snack. If you walk the entire trail you will end up at Navy Pier. We walked the trail half way and then enjoyed some snacks on a bench before turning back to head to the city center for our boat tour.

Take an Architectural River Boat Tour

While many come to Chicago for good food and great vibes, others come to admire its’ amazing architecture. Home to some of the top architectural design schools in the country, Chicago riverfront boasts some of the most intricately designed and tallest buildings in the United States. One can embark on a 45-min or 1.5hr river boat cruise to check out these works of art up close. A boat cruise is the perfect way to see the art and the city skyline, especially at night! I booked a 45-min tour via booking.com (~$45 per person).

Try Deep Dish Pizza

Chicago is home to the original deep dish pizza. I won’t try to convince you of the best place to get pizza, because there are so many “best” spots, but we tried Lou Malnati’s. I am not a fan of deep dish, but I had to give my husband the full experience on his first trip to Chicago. Wherever you decide to go make sure you make a reservation a day or so in advance. Deep dish pizza takes ~40 min to bake, so restaurants can have an hour+ long wait!

Get a Massage

After walking nearly 20,000 steps, we were exhausted! We spent the morning doing the highlights so that we could have a slow afternoon. I am a big fan of massages, especially Thai style. I called around to a few top rated places and was able to make a same day couples appointment for $160. It was the perfect way to start winding down our afternoon after a busy morning. We visited Thai Lotus Body Work, and the ladies put our bodies to work! It was amazing! I highly recommend.

Check Out a Rooftop Bar

There is no better way to wind down or wind up your evening in Chi-town then sipping a cocktail and soaking up the sky high city views. I had the London House rooftop bar on my wish list for years and luckily we were able to walk right in around 4pm and get a spot at the bar. Reservations are only necessary if you plan to dine, but for drinks only it is first come first serve. I would have loved to experience this bar and the view at night!