Chicago is a city that has been on my list to visit for awhile, so when The Tall Man texted me about an opportunity to go for a weekend, my immediate answer was yes!
The Tall Man and I flew in early on a Saturday morning, and we immediately hit the ground running. When you only have a limited number of hours in a city and your one evening is for a work event, you take advantage of every minute! Here are our suggestions of things to see and do when you have a very short amount of time to explore The Windy City.
The Chicago Bean
The Chicago Bean is probably one of the more popular sculptures in the city and is a “must” for most tourists. The Bean creates the perfect opportunity to capture the city’s skyline and get yourself in the picture. Located in Millennium Park, Cloud Gate (the actual name of the sculpture) was created by British artist Anish Kapoor and completed in May 2006. The sculpture is open 24-7, but it is definitely more crowded on the weekends. The Bean also overlooks the McCormick Tribune Plaza, which serves as a public ice skating rink in the winter months and dining plaza during the summer.
Cardigan (no longer available) (similar) // Cami // Jeans // Boots (similar)
360 Chicago at John Hancock Center
There are several places throughout the city to get glimpses of the skyline, but the two more popular options offer 360-degree views of the city from above. The first is the Skydeck at the Willis Tower and the second is 360 Chicago at John Hancock Center. A lot of people opt for the Skydeck, but after asking around and doing our research we decided to take on 360 Chicago and its Tilt! We ended up having a beautiful clear day to see all of Chicago, and we got a kick out of the Tilt experience. It is definitely worth adding to your list!
Walk the Magnificent Mile
The Magnificient Mile is a 13-block stretch of North Michigan Avenue that runs from the banks of the Chicago River. These blocks encompass over 400 stores and 200 restaurants. It aslo has some incredibly rich architecture, and we definitely want to do an architecture tour on our next visit.
Explore Museums
Chicago has a plethora of museums on a variety of subjects. We opted to take on the Museum of Science and Industry, located in Hyde Park. We only had a few hours to explore, but this is definitely on our must-see list when we return. The three exhibits we saw were: the museum’s first exhibit, Old Ben No. 17; the Mirror Maze; and Toymaker 3000. Some exhibits have an additional charge to your entry ticket, so make sure you check as you plan your visit.
Check out this video of me getting lost in the Mirror Maze.
Food
The Tall Man and I like trying “local” restaurants when we visit new cities. I put it in quotes because they may be a chain restaurant in the area we are visiting, but it is something we can’t get at home. During our visit, we checked out a couple of seriously good restaurants in the city. See below for our list and recommendations.
Park & Grill – Located in the McCormick Tribune Plaza under The Bean, this restaurant was our first taste of Chicago. It is on the pricey side (especially for lunch), but the food was amazing! We recommend the Shaved Prime Rib Sandwich and the House Roasted Turkey Sandwich.
Shula’s Steak House – This steakhouse is located in the Sheraton Grand Chicago (our hotel), and it is where The Tall Man’s work event was hosted. We had a delicious prime rib dinner and enjoyed the company of The Tall Man’s co-workers. If you get the opportunity to get a delicious steak in Chicago, I highly recommend it. It was probably one of the best steaks I have had in a while.
Eggy’s Dinner – For brunch on Sunday, we chose Eggy’s Dinner. I’m so glad we ended up at this place. It was a super small, very cute space and the food was really good too. We recommend the Cinnamon Roll Pancakes and the Eggy’s Crepes.