Oh man, I had hoped to write and publish this post last week, but it ended up being a much bigger undertaking than I expected and work has been insanely busy, leaving me very little free time to focus on blogging. Alas, I had the weekend to get this done so here’s my last Chicago recap!

Our third day in Chicago (Wednesday) was a fun one, but it was also the day we had the scariest Lyft drive of my life. We’ll get into it!

We slept in on Wednesday, something my mom was very grateful for. We had a noon reservation at the Shedd Aquarium so we didn’t have to get going until around 11 or so, which was really nice. I didn’t think I was going to sleep late (I set an alarm for 9:30), but I wound up needing that alarm. I guess I was tired!

We started our day by checking out Wildberry Cafe. I already had it on my list to try, but when my mom posted about our trip on Facebook, one of our family members told us to go there! So we definitely had to make it happen. There was a Wildberry within walking distance of our hotel and we were seated nearly immediately, but damn, they were not following any COVID procedures here, let me tell you. None of the servers wore masks and they seated us within 3 feet or less of other patrons. Eeks!

Even so, Wildberry was a delicious breakfast spot! Mom and I shared a plate of chocolate chip pancakes and I also got a side of eggs and bacon. We planned on having a big breakfast and skipping lunch, so I knew I needed something that would keep me satisfied for hours. It was such a great breakfast, and I am still dreaming about those pancakes. Mmm!

We got to Shedd right around noon and spent about two hours walking around this sensational aquarium. It was the one thing my mom wanted to do while in Chicago, and I’m so glad we went. The aquarium is filled with tons of little exhibits with fish and eels and sharks and turtles and penguins, oh my! (Somehow we missed the penguin exhibit, which I am very sad about.) They also have an oceanarium where you can watch beluga whales and dolphins swimming around. Apparently, they also have sea otters but they weren’t around on the day we went, wah.

One of the more disturbing experiences at Shedd was watching a shark documentary, which came with our ticket. There were some cool tidbits in the documentary (like epaulet sharks who can breathe and walk on land for a period of time) but there was also a lot of information about how sharks entice their prey that was hard to stomach. Let’s just say there was a scene involving seals happily playing while a great white shark hunted them that would have scarred me for life if I watched this documentary as a child. Even as an adult, I hid my eyes behind my hands during that scene!

Aside from that disturbing documentary, we had a great time at Shedd! We probably could have spent more time there but we wanted to hit up the Field Museum, which closed at 5pm, so we left a little after 2.

The Field Museum was great, but I should have done my due diligence beforehand and figured out which exhibits to check out because we missed so many great ones! (Including Sue the T.Rex, wah!) Some of the exhibits were interactive, which was fun, and our ticket came with the option to watch a short documentary about Titanosaurs, which is the largest dinosaur to ever roam the Earth. It was a pretty cool documentary! (Much better than watching sharks hunt seals, for sure.) We strolled through a few exhibits afterward and I found one about African culture particularly powerful.

We left the Field Museum around 4:30 and I ordered a Lyft to take us to a local bookstore. It was the first time I’ve ever been in a Lyft and felt uncomfortable with the driver. He wasn’t doing anything particularly problematic, but he seemed to be driving us in circles to get to the bookstore. What should have been a 10-minute drive ended up being double that! I was following along in the app and he kept going straight when he needed to go left, or turning right when he needed to go straight. I’ve had drivers not follow the GPS directions before, and that’s fine as long as I see a logical path to get to my destination. This driver was just going in circles (almost as if he was trying to earn more money by driving around longer). I started feeling really scared, unsure if he would ever get us to our destination. Multiple times I wanted to just get out of the car. Eventually, we made it to the bookstore and the driver gave me a line that his GPS not working correctly (I was sitting behind him so I couldn’t see his GPS, but I don’t buy that excuse one bit). I was pretty upset with the Lyft app, though, because they typically will send an alert when a ride is taking too long or the driver is going off their GPS, but they didn’t send me anything until AFTER it was over. Not very helpful, Lyft! (I did send a complaint, though.)

But we made it to the bookstore at least?! After-Words Bookstore has an eclectic collection of both new and used books, and it was a cute little shop with the ground floor filled with children’s books and a downstairs section for adult books. I was feeling very unsettled from the Lyft ride and didn’t feel like I could peruse as leisurely as I wanted to. I did end up settling on two books to bring home with me (I bought The Most Fun We Ever Had because Claire Lombardo is a local author!); I love buying books that remind me of my travels in some small way.

After our short trip to After-Words, we were ready for an early dinner. I wanted to visit Shake Shack at least once while we were in Chicago since I’d never been. We found one within walking distance of the bookstore, yay!

For me, Shake Shack was a bit underwhelming! It wasn’t bad—I liked my burger more than I liked the fries—but it wasn’t so good that I left the restaurant bereft that the only location near me is 20 minutes away. Give me BurgerFi any day! Mmm. (My mom ordered their beer and she really enjoyed it!)

And that was Wednesday! We walked back to the hotel, enjoyed an episode of Big Brother, played some games of Qwixx, and then packed up our room a bit since we would be flying back home tomorrow. But we had one more adventure to enjoy!

On Thursday morning, we were up and at ’em early as we had a 9 a.m. reservation at Skydeck Chicago, which is located in the Willis Tower. We traveled up 103 floors to see gorgeous views of the city. At this observation tower, they had The Ledge, which is a glass box that extends out a few feet from the building so it feels like you are standing right on top of the city. It’s pretty cool, but I got a lot of comments from people about how scary it looked when I posted the photos/video on Instagram. I’m not someone who’s scared of heights (I’ve ziplined multiple times and grew up on roller coasters, lol) so it was mostly an insanely cool experience rather than a scary one. I can definitely understand that it’s not for everyone! But it was so worth it to me.

We took a few loops around Skydeck since it wasn’t very busy and we had the time. I’m really glad we squeezed in this one last Chicago adventure before heading to the airport.

I had such a good time in Chicago and I’m so glad we made this trip happen, even though the Delta variant is surging. (I took a COVID test when I got back and it was negative, thank goodness!) It was a good time with my mom and I desperately needed the time away from work and life to enjoy an honest-to-God vacation, something I haven’t had in almost two years at this point! It was everything I hoped it would be, and I can’t wait to return to Chicago soon. This city has carved out a special place in my heart.

We began our second day in Chicago with a visit to Stan’s Donuts, which I was really excited to try! While I wouldn’t consider donuts to be a favorite of mine, give me a specialty donut shop (even better if they serve mini-donuts!) and I’m a happy girl. Unfortunately, it wasn’t a hit for us. My mom found her donut too bready and while my donut was good, it was also a little dry and almost tasted like those little Hostess chocolate donuts you can get at the grocery store, lolz. Oh well. At least we had fun plans in store for us today: a visit to Navy Pier and 360 Chicago!

We arrived at Navy Pier around 10:30, only to find out that they don’t really get going until 11. Oops – just means we had time to stroll around the pier and take in all the sights! We bought tickets to ride the Centennial Wheel, which is what I wanted to do the most here. And it was well worth the wait! Apparently, in pre-COVID times, you had to share one of the gondolas with other people, but not right now! I was very happy that we had a gondola to ourselves, COVID or not. (Listen, as a shy person with social anxiety, some COVID procedures vastly benefit my life.) The gondola was fully enclosed and air-conditioned, which was really nice. We got to do three loops around and see all of Chicago. It was amazing! I highly recommend a visit to Navy Pier just for this experience.

We ended up doing the Wheel for a second time because we loved it just that much.

Afterwards, we wandered around the pier to find something to eat and stumbled on Harry Caray’s Tavern where we ordered some drinks (I couldn’t pass up a frozen drink! It reminded me of being on a cruise ship!) and lunch. My mom had her first Chicago dog experience and she was super happy with it! I ordered a burger and it was fine—nothing to write home about. (Should’ve gotten the Chicago dog, I think!)

We had some time to kill before our reservation at 360 Chicago so we walked around the pier and stumbled on an indoor pavilion with lots of kitschy shops. This is where I picked up one of my only Chicago souvenir of the trip, which was a magnet. I love it and it makes me smile every time I see it. We also found a bakery and got a cupcake to share, but eh, it wasn’t very good. We should have opted for Ben & Jerry’s! Live and learn.

Then it was time to order a Lyft and head over to 360 Chicago! I was super, super excited about this excursion. Here, we took an elevator (thank god) to the 94th floor of the John Hancock building where we got to see incredible views of Chicago. It was truly magnificent! It was hard to believe we were so high up (we don’t have buildings like this where I live, that’s for sure) and could see so many miles of the city.

(I wore a mask while inside the building, but took it off for this photo since there was nobody else around me.)

We also took part in TILT, which is a “ride” in which you stand on a glass box, hold on to handlebars located at both ends of the box, and then try not to freak out when the glass wall in front of you starts to tilt down onto the city! Y’all, IT WAS SO MUCH FUN. It tilts down about 30 degrees and was such an insanely cool experience. I was nervous about it because when we were waiting for our turn, there was a couple in the Tilt ride and the male participant couldn’t handle it! He kept stepping back because it freaked him out so much. But it really wasn’t bad at all! (Zip-lining is much scarier, lol.)

After enjoying TILT and taking two spins around the observation deck, Mom and I got a drink and relaxed in comfy chairs, sipping while enjoying the view. Ahh… I love vacation. 🙂

We took a Lyft back to the hotel afterward and then it was time for our daily nap! Yessss.

Tuesday evening, we ventured out for pizza! Both of us are pretty darn picky about our pizza, especially when it comes to crust. We certainly didn’t have plans to try deep-dish pizza because ick. I’m very happy for you if you love deep-dish pizza, but it’s just not for us. Thankfully, most of the famous Chicago pizza places offer thin-crust pizza alongside deep dish, so we were able to get some pizza anyway! We decided on Giordano’s, mostly because it was the closest pizza place to our hotel and we weren’t feeling up to too long a jaunt for dinner.

Verdict? It was okay. It wasn’t outstanding, but we both easily polished off a small pizza between the two of us. The weirdest thing about the pizza was that the cheese just slid right off the slice! No staying power here. I haven’t encountered that before. All in all, it was fine but nothing to write home about, you know?

After that, it was back to the hotel for a few rounds of Qwixx before we took to our respective beds to read our books. 🙂 Tomorrow was going to be another busy day but this time, I let us sleep in!

Our trip to Chicago was wonderful! While I don’t think any city will capture my heart quite like Savannah (I’m definitely overdue for a trip there!), Chicago did its damned best to come close. I loved everything about this city! The tall, tall buildings that surrounded me whenever I walked around the city, the beautiful Chicago River, the gorgeous weather (<– good thing I didn’t come in the winter, eh?). It was easily one of the best cities I’ve been to and I can’t wait to return someday soon.

We arrived in Chicago on Sunday around 4:30pm but didn’t make it to our hotel until after 6pm, whew! It’s quite a drive from O’Hare to downtown Chicago! (Not to mention, it felt like we walked the entire airport to find the Uber/Lyft pickup area!) Eventually, we checked into the hotel (we stayed at the Hyatt Regency right on the Chicago Riverwalk) and were greeted with this amazing view:

Okay, Chicago, I am already impressed by you! 🙂

We didn’t do too much on Sunday night, aside from catching the latest episode of Big Brother and having a meal in the hotel bar. We thought about venturing out for dinner, but we were worn out and were going to have an early start to our day, so we opted for something easy.

On Monday, we kicked things off with the famous architectural boat tour, which I have heard so much about from other people who have traveled to Chicago! As a lover of all things history, I knew I wanted to fit this into our schedule. And I’m so glad I did because it was magnificent! (We went with the Chicago’s First Lady boat tour, thanks to a recommendation from Kim!) The boat winds slowly up and down the Chicago River for an hour and a half, and we had a historian from the Chicago Architecture Center telling us all about the different buildings, their architecture, and what they all meant for the Chicago skyline and the city as a whole. I was fascinated from beginning to end, and we really lucked out with the weather, too. Sunny in the mid-70s with a nice breeze – perfection! (Even the historian kept remarking how this was the most beautiful day he’d ever seen in Chicago!)

(Sorry for the Trump Tower in the background of this photo. *shakes fist*)

After our tour, we took a quick jaunt over to Millenium Park so we could see the Bean! It was so cool to finally see it in person after only ever seeing it in pictures on social media. It was also much dirtier than I expected? Haha. I don’t know why I would think it was this pristine landmark when thousands of people likely flock to it on a daily basis. Of course it gets dirty! But it was still a delight to see.

After seeing the Bean, we had to deal with an injury—the first and only of the trip, so that’s major progress for us. My mom got a bad blister on her right foot but thankfully, there was a Walgreens right next to Millenium Park so we headed over there for bandages. By then, we were getting hungry and I was hoping to eat at Park Grill and then do a little more exploring, but the restaurant was closed. Womp, womp!

Instead, we found a different restaurant that was close to our hotel: Sweetwater Tavern. I know my mom wasn’t feeling great from her blister, even with the bandages, so after a delicious meal, we headed back to the hotel for naps before dinner. We did this every day we were in Chicago, and I highly recommend it. Could we have pushed ourselves and seen more of Chicago? Sure, but that’s just not the kind of travelers we are. We value rest and it was really nice to take a break after our adventuring to relax in our room.

Monday evening was the highlight of my whole trip, as I finally got to meet (and hug!!) Kim. We’ve been reading each other’s blogs for a long, long time and she’s become someone I feel really comfortable confiding in, and it was such a joy to be able to have dinner with her. And she brought us rocks! Kim is a super-talented rock painter and I was so touched that she created an adorable rock of Chip and Lucy for my mom based on one of their Instagram photos as well as brought me my own “cat mom” rock.

We met at Quartino Ristorante for dinner and it was delicious! There were so many yummy options on the menu that it was hard to choose what to eat, but I stuck with my old favorite (chicken parm) and we ended the meal with gelato (for mom and me) and sorbet (for Kim). It was lovely to just chat with Kim – we could have honestly sat there for hours and hours, but alas. We had to wrap it up since Kim had an hour-long drive home. I am so grateful to her for driving into Chicago to meet us for dinner! Yay!

Have you ever been to Chicago? What’s your favorite U.S. city you’ve ever visited?