H and I just returned from a long weekend trip to Chicago — a city I first visited and loved in 2016, and it was so fun to go back. We were there for a wedding, but flew over on Thursday to enjoy the sights and experiences more. I was (and still am) 27 weeks pregnant — and now just a day away from 28 and the third trimester. I definitely felt a difference in traveling at this stage; H and I typically like to pack in all the activities when we travel, but I became tired much more easily and had to pace myself and make time for rest. We were still able to do a lot, and it was a wonderful time. I’m really grateful I was able to go — all while feeling more and more baby movements as our little guy grows.
On Thursday, we arrived mid-afternoon and took a taxi to our hotel, the Hilton Chicago, which we booked without much expense thanks to H’s job and where we had a view of Lake Michigan. On my last trip with my mom and cousin, we stayed at The Talbott. I really enjoyed being on Michigan Avenue and so close to the main sights.
After getting settled in our room, we took a leisurely walk down the street toward the Art Institute and back. We got changed (I wore this super comfy jumpsuit) and headed downstairs for dinner at Kitty O’Sheas — a restaurant in our hotel — and then walked a few blocks to the Studebaker Theatre to see Wait Wait… Don’t Tell Me!
They do the show live every Thursday evening, and then it airs on Saturday morning (and again on Sunday, at least on our local NPR station). H and I are longtime fans of the podcast, and it was really fun and entertaining to be there in person for the live, unedited version!
We haven’t listened to the recorded show yet but look forward to doing so and hearing how they edited it all. I highly recommend this experience if you’re a fan of the show.
Friday morning, I wore one of my favorite go-to dresses this summer, and after breakfast at the hotel, we walked outside and greeted the gorgeous, sunny day. We first walked to Millennium Park and saw “The Bean.” I admired all of the colorful blooms planted along the streets, sidewalks, and walkways.
We then headed back to the Art Institute once they opened at 11 and toured the museum. It is truly a fabulous collection; Impressionism is my favorite, so we spent the most time viewing those pieces.
After a few hours, we walked across the street to the Chicago Athletic Association. We first headed up to the rooftop to see if we could get a table at Cindy’s, but it was packed — however, we did get to see the gorgeous view.
We then made our way to the lobby and ate in the cozy Drawing Room, which felt like being in the Gryffindor Common Room or another nook in Hogwarts. I had a delicious, fresh salad.
I was feeling quite tired by this point, so we returned to the hotel after lunch, and I took a long nap. H discovered an outdoor deck at our hotel by the pool and fitness center, so I went to sit and relax in the sun for a while.
We then got changed (this dress and sneakers for me, since the attire was casual) and took a taxi to Hopewell Brewing Company, located in Logan Square, which seemed like a cool area with a lot of great restaurants, for the welcome party to kick off the wedding weekend.
I slept for a long time Saturday night and woke up feeling more rested, and thankfully felt pretty good all day. It was stormy through breakfast, but cleared as soon as we were ready to venture out. We took a taxi up Michigan Avenue (if I wasn’t pregnant, we likely would have walked!) to the Magnificent Mile for some shopping. We popped in a few stores (the Harry Potter Shop was crowded but impressive, like a mini Harry Potter World, without the rides) and ended up buying a few baby clothes at H&M.
After shopping, we sat for a lunch reservation at RL Restaurant, where I had been and loved on my last trip and wanted to return. It was just as fabulous! We sat on the patio since the weather was so lovely, and it was a dream — the atmosphere and food and everything. I highly recommend enjoying a leisurely lunch here after doing some shopping.
My energy had not yet waned, so after lunch we hopped in another taxi and went to the Shedd Aquarium just for fun. Admission was costly, and it was quite crowded. The highlight was seeing the beluga whales — they were so cute, and we had the opportunity to see the staff feed and play with them.
After our aquarium adventure and resting at the hotel for a few hours, we got dressed up and took a taxi back up Michigan Avenue to the river for the wedding celebration at the McCormick Bridgehouse & Chicago River Museum. It was just a beautiful evening, which made the outdoor affair extra lovely. There are five flights of stairs to the top of the narrow building — with history and information along the way — and despite being pregnant, I climbed them (taking breaks as needed)!
We walked (slowly and carefully) back down and enjoyed the rest of the evening on the terrace eating, chatting, and soaking up the views of the river, surrounding buildings, evening sky, and the boats going by. (Last time I was in Chicago, we did an architecture boat tour, which was very cool and informative, and well worth the time!) This evening was a beautiful conclusion of our trip.
We woke up early Sunday for our flight back to Nashville, and saw the sunrise over Lake Michigan. Chicago is such a fun city to visit, and so close to Nashville! I’m glad I was able to take this trip and enjoy the weekend before I become too pregnant. Someday I’ll tell our baby boy how he came with us this summer to Jackson Hole, South Carolina, Rhode Island, and Chicago.
Have you been to Chicago, and what are your favorite things to do?
