Hi, I’m Katie! Are you new here? Welcome!
I’m a travel advisor with The Magic’s Yours Travel and I send clients on vacations of all kinds all over the world. My specialty is Disney travel!
Want to work together? Please check out my website katievtravel.com to request a vacation quote or email me at katiev@themagicsyours.com with any questions. I’d love to make your vacation dreams a reality!
I love a long weekend trip to a big city! In my opinion, it’s the perfect length of time to explore a city without feeling overwhelmed by too many days of hustle and bustle. This past Labor Day weekend, my husband, Scott, and I visited Chicago, Illinois. We chose Chicago as our destination because Pearl Jam was performing at Wrigley Field that Saturday night and, as a big fan of the band, seeing Pearl Jam at Wrigley Field was on Scott’s concert bucket list. He was lucky enough to get tickets when they were released so we planed a trip to Chicago around the concert. We had visited “The Windy City” once before in 2017 and although this trip centered around the concert, we were able to fill the weekend with new (to us) Chicago experiences.
Day 1 : Arrival & Hotel Review
Departing on Friday evening we took a quick flight from Baltimore (BWI) to Midway (MDW) in Chicago. It was simple to grab a rideshare from the airport and the drive took about twenty minutes to our hotel in downtown Chicago, the Homewood Suites by Hilton Chicago Downtown/Magnificent Mile.
Here is my review of the hotel! The Homewood Suites by Hilton Chicago Downtown/Magnificent Mile is in a fabulous location for sightseeing. It’s right in the middle of Michigan Avenue making it walkable to many popular sites as well as the L rail system which can get you anywhere in the city. It’s also easy to get a rideshare from this location. Tons of dining options are within a quick walk including a Chipotle, which is attached to the hotel lobby, several nearby coffee shops, and more elevated dinning options. The Magnificent Mile is covered with high-end shopping opportunities like Tiffany’s and Ralph Lauren as well as tourist shops selling candy and local sports teams’ gear. There was a Walgreens two blocks away for any last minute necessities and we were able to get an Instacart delivery from Target which was very helpful in stocking the in-room kitchen.
This is a high-rise hotel which means you’ll be relying on elevators often. We had to wait at least five minutes each time we needed one but discovered the service elevators were being repaired during our stay so housekeeping needed to use the guest elevators. It’s likely that wait times would be shorter when all the elevators are functioning.
The hotel included breakfast which offered hot and cold buffet self-serve options. The breakfast room was comfortable and well-appointed with plenty of seating. I would say the food offered was standard hotel breakfast fare and medicore in quality. It’s always nice to have this option included, especially if you’re just trying to grab something quick before a busy day, but it was nothing special.
Our room was categorized as a Studio King and was located on an upper floor with city views. The main area of the room was spacious, for a city hotel, with plenty of seating and had an enormous walk-in closet. The bathroom was a bit tight however. Every room in this hotel offers a full kitchen and I absolutely love that amenity. This allowed us to make our own meals several times and keep snacks handy. The room, however, was in need of a spruce for sure. The paint and linens has seen better days and the room was clean but a little dingy from age. The best part of this room was the view! With floor to ceiling windows looking out over Chicago, we could see the famous architecture all around us. The views were stunning day and night. I spent a lot of time Googling the name and history of the buildings I could see.
There were hits and misses about this hotel but overall I was happy with our stay, especially the fabulous location of the hotel.
Day 2 : Exploring The City & Concert
The next morning we started the day with a visit to the Starbucks Reserve Roastery Chicago which was just a few blocks from the hotel. This is the largest Starbucks in the world with four beautiful floors of coffee. The first thing I’ll share is that you need to be prepared to wait in line. There seemed to be a constant line all day long winding out of the building and we ended up waiting about 45 minutes in total. In addition to a typical Starbucks on the ground floor, there were also two gift shops, an area where they offer tastings and coffee classes (which you need to register for in advance), a coffee bar, plus a counter where you could order from a full menu of pastries, sandwiches, flatbreads, and similar. Of course they also have a menu of extra special coffees, including roasts you can only get here, and coffee flights. All of the coffee served here is roasted in-house. You could easily spend many hours at the Roastery having an extensive coffee experience. I think it’s a must-visit for frequent Starbucks customers or coffee lovers. We had the Chicago Blend coffee and really enjoyed it.
Our next stop for the day was the Chicago Architecture Center. This is the hub for the famous Chicago architecture boat tours as well as many architecture walking tours. We opted to just visit the museum portion which was underwhelming. It was very small and really more of a welcome center than a museum. I think the center makes a nice addition to one of their tours but is not worth the stop on its own. I’m definitely interested in taking one of their boat tours in the future, however. I highly recommend walking across the DuSable Bridge on Michigan Ave, right next to the Architecture Center, to see the fabulous views of the river and all the awesome buildings.
Next up was the American Writers Museum, a fifteen minute walk away. Located inside a high rise office building, the American Writers Museum was very small but I enjoyed the exhibits celebrating writers, their work, and the craft as a whole. I think this is a fun stop for avid readers of any age but a great fit especially for teens and pre-teens who will appreciate the content and the interactive elements especially.
For lunch, we dined at LYFE Cafe which is a counter-service restaurant that focuses on healthy food options with global flavors, local produce, earth-focused practices, and plant-based options. This was a great option for my food allergies as the menu noted allergens on it and had a variety of options. I had salmon with mixed veggies and lentils which was delicious. Scott had buffalo cauliflower tacos which he enjoyed as well. This was a great quick lunch stop!
After lunch we took a break at the hotel, made dinner, and got ready for our evening. As I mentioned, the impetus for this trip was the Pearl Jam concert at Wrigley Field, the Chicago Cub’s baseball stadium. The concert was great!
I want to share some logistics about getting to Wrigley Field that will be helpful if you’re attending a baseball game, ballpark tour, or another event a the stadium. Wrigley Field is one of the oldest ballparks in America and is located in the middle of a neighborhood. There are some restaurants and bars surrounding the park but walk a block over and you are strolling past adorable houses.
We took the L rail public transit system from the Magnificent Mile area of our hotel to Wrigley Field. As someone who only uses public transit a few times a year, I found it easy, efficient, and economical. It was also very cramped and kinda dirty, as most city rail systems are. There are parking lots available, if you have a car while traveling, though some lots require a bit of a walk to get to the stadium.
On the way home, we wanted to avoid the huge crowds on the L, so we opted to take a rideshare back to our hotel. It’s important to know that rideshares cannot pick-up near the stadium but there are several designated pick-up locations a few blocks away. Plan ahead of time which of these areas you want to use and prepare for crowds all trying to do the same thing. This is certainly a less crowded and more comfortable option than the L but probably took about the same length of time and cost more.
Day 3 : Art Institute
To start the day, we visited Stan’s Doughnuts & Coffee to grab coffee, a quick walk from the hotel. A Chicago-based chain, Stan’s has a happy and brightly colored atmosphere. I really enjoyed the coffee which had a strong, nutty flavor. We didn’t have any of the doughnuts but they looked fabulous!
First on today’s agenda was the Art Institute of Chicago which is located on the edge of the park corridor right next to Millennium Park. The huge stone building’s main entrance, on Michigan Avenue, is flanked by the iconic bronze lions. While you’re there, make sure to peek across the street and spot the brown street sign that marks the start of Route 66. Once inside, you can grab your entrance ticket and, as required, check any backpacks or larger bags you may have with you. The Art Institute is a labyrinth of fantastic art across mediums, time, and origin. There is so much to see here!
I was overwhelmed by the volume of art as each room seemed to lead into another and another. You could easily spend an entire day here. I highly recommend doing a bit of research, in advance of your visit, to discover what collections might be on your must-see list. When you arrive be sure to grab a map as well. They have a cafe that offers lunch or you can pack food and have a picnic at one of the nearby parks.
I’m far from an art critic or expert but I was very impressed with the breadth of the collection here. There seemed to be something for every interest and a number of pieces that are extremely well known. The highlights for me were the entire Impressionist exhibit, Tiffany glass, and Grant Wood’s American Gothic. Also notable was a large collection of European medieval armor, Edward Hopper’s Nighthawks painting, Japanese screens, and the Thorne Miniature Rooms (imagine epic dollhouse recreations of homes from different time periods and locations).
After spending about three and half hours at the Art Institute, we walked next door to Millennium Park to visit Cloud Gate a.k.a. The Bean. This large sculpture is a Chicago icon and I love to take photos in places like this. Of course, I was far from the only one with this idea so if you want photos without lots of other visitors in them you’ll want to stop by early in the morning.
After taking some photos, we made the walk back up Michigan Avenue to our hotel, stopping in a few shops along the way. We picked up an afternoon coffee at the adorable Ralph’s Coffee Co., located in the front of a Ralph Lauren store, the coffee here was another hit for us. After a bit more window shopping we called it a day and went back to our hotel to pack and make dinner.
Chicago Coffee Rankings:
- Starbucks Reserve Roastery
- Stan’s Doughnuts & Coffee
- Ralph’s Coffee Co.
Day 4 : Departure
It was time to leave the next morning so we took a rideshare to Midway airport and arrived in Baltimore by mid-day.
I thoroughly enjoyed my time in Chicago! After this second visit to the city there is still so much more to do on a future third trip. I have my eye on that architecture boat tour! I’m certain I’ll be back to the Windy City one day soon.
That was our Chicago trip! I hope you found this interesting and informative. Considering a trip to Chicago?
I’m a travel advisor and would love to work with you!
Check out my website katievtravel.com to request a vacation quote or email me at katiev@themagicsyours.com with any questions.
I’d love to make your vacation dreams a reality!
Katie Vassalotti - Travel Advisor - Travel Blog 