A few months ago, when Dave mentioned he had a business trip to Chicago coming up, I knew I wanted to tag along, and I’m so glad I did. I’ve always wanted to visit Chicago, and I came away with some serious fondness for the city — although, let me tell you: it was super cold for this California-living, Florida-raised girl. Brrrrr!
For four nights and five days, we soaked up the city and packed a lot in, while also having plenty of down-time, as well as a great surprise. Let’s get right into highlights from our time there …
Fitness, healthy food and blogging buddies
My first full day in Chicago, I was on my own while Dave worked, so I fit in a workout at Lagree Studio and had two dates with blog friends. Because our hotel (we stayed at the Loews) was centrally located, I was able to walk to all my activities, which was super nice. I started out with a 50-minute reformer Pilates class at Lagree Studio on East Erie Street in the River North area. The class was tough from the very first minute and had a huge focus on core, legs, arms and balance. We each had our own reformer to work on and all of the exercises were done on there — no cardio, just strength — with some cool tunes and a good instructor to guide us along. I loved the burn and the shake and would really enjoy incorporating more reformer Pilates into my current fitness routine. Thanks to the folks at Lagree Studio for welcoming me in for a complimentary class. Come open a studio in Walnut Creek, please!
From there, I went to Sweetgreen to have lunch with Erin. Erin and I met at BlogFest in LA two years ago and have stayed in touch via the blog world since that time. She’s a fitness gal and a foodie, and we enjoyed catching up on life and what we’re working on. Oh and Sweetgreen? So healthy and SO good! I wanted everything on the menu.
Later that afternoon, I had a very long hot chocolate date with Susie at Dollop, near my hotel. We hung out for a couple of hours chatting about life, and I was even lucky enough to get to meet her hubby, Alex, who stopped by at the end of our date. Loved that!
I have to thank both Susie and Erin for hanging out with me and for giving me so many recommendations for things to do and places to eat in Chicago. There were so many, we couldn’t hit them all.
The views from Skydeck Chicago at the Willis Tower
On Friday morning, Dave and I went over to the Willis Tower (formerly the Sears Tower) to experience the view from 103 floors up. The exhibit has a little museum, an introductory movie and lots to look at as you wait in the lines for the main event. We were lucky that it wasn’t a very busy day, so we were through the bottom floor and boarding the 60-second elevator ride up in no time. Once at the top, we waited in line to step out onto the glass Skydeck Ledge, and it was way scarier than I had anticipated. I actually had to take a deep breath before stepping out on the glass more than 1,300 feet up in the air.
We took a few pictures and seriously enjoyed the gorgeous view — spending about an hour at the Willis Tower total. Thanks to the folks at SkyDeck Chicago for offering us complimentary tickets! It was a major highlight to see so much of beautiful Chicago from the tallest building in the Western Hemisphere!
A huge surprise appearance by visiting friends
Perhaps the true highlight of my trip to Chicago was the surprise that I had, which lasted the weekend. On Friday, when Dave and I arrived to lunch at Lou Malnati’s Pizzeria for some deep dish pizza, I was completely taken aback when we approached our table and our best friends, Grant and Bre, were sitting there waiting for us. Grant and Bre live in Columbus, Ohio, and we were last with them on our amazing Las Vegas trip in August. They used to live in Florida as well, and we try to meet up for fun times at least once a year. I was completely shocked to see that they made the six-hour drive to Chicago to hang out with us over the weekend, which Dave seamlessly arranged with them, including getting them tickets to the show we had planned to see and keeping us on schedule so we arrived at the surprise on time.
It was awesome! They are so fun, and the perfect traveling friends. They like to eat, they like to laugh, they are up or down for anything, and we totally enjoyed our 48 hours together! We have so many inside jokes and memories, and there was no better group to explore Chicago with.
Absolutely delicious food and restaurants
I didn’t take a single bad bite of food over the five days and four nights I was in Chicago. I had delicious take-out one night from Lyfe Kitchen. I loved my salad at Sweetgreen. I loved my hot chocolate at Dollop. And a few other highlights …
RPM Italian, which is part-owned by Bill and Giuliana Rancic. This place was a super-cool scene, and the food was amazing. Our group of four ended up securing a high-top table in the bar area after waiting for 45 minutes or so, and we then ordered about eight things from the menu, sharing each item one at a time. We had spicy squid ink pasta, a steak, spaghetti and meatballs, truffle garlic bread, and three desserts, and I really can’t pick a favorite. Our service was great, the music was on point, and we loved this dining experience!
Lou Malnati’s Pizzeria, which we were told had some of the best deep dish pizza. It was so good. I had a cheese personal pan pizza, and it was mouthwateringly fabulous. I wish I had eaten there more than once on our trip, because Chicago makes some good pizza.
Stan’s Donuts, which has a few locations in Chicago. Listen: I don’t usually eat donuts. They just aren’t my treat of choice, but after having a green old-fashioned pistachio donut at Stan’s, I may be a donut person. Apparently it’s the best-selling item, and was deliciously unique. So good!
Wildberry Pancakes and Cafe, which is a very busy place boasting a wait-time of more than two hours. I figured out we could check into the wait-list online, so we got there about 10 minutes before our table was ready, which was so convenient. I ordered a veggie omelet and a side of fig and walnut pancakes. And these pancakes were the best I’ve ever had! Everyone else loved their meal as well.
Goddess and the Baker, which is a small bakery with multiple locations around the city. So many healthy and colorful options! I had a green tea latte and a scone for breakfast that day, and I actually wanted just about everything on the menu. Highly recommend this place for its cute decor, good service and selection of goodies.
The Vig, which was a place we ate dinner in the Old Town neighborhood before a show. The place had a great environment, and we shared a ton of appetizers and desserts, and the stand-out was definitely the lobster-filled deviled eggs — OMG. Great service, great food and a comfortable place to hang with friends. The crowd was young and looked so different from what you would see in San Francisco, so I totally loved the people-watching there too.
Laughing out loud at The Second City show
I really didn’t know all that much about Chicago before visiting, but one thing I did know was that The Second City was located there. I had heard of The Second City when reading Amy Poehler’s book, because it’s the place where many, many Saturday Night Live actors get their start. And the show, in its 105th revue since opening, did not disappoint. In fact, it was even more enjoyable than I could have imagined. There were only six actors, and they performed some pre-planned stage shows, as well as did complete improv based on audience input. Of course, some of the comedy was off-color and political, but everyone in the tiny theatre laughed at it all.
The funny thing about that night was that there was a high school group from Canada in the audience, and we were basically in the middle of the group of kids. I cannot imagine a high school teacher thinking that the comedy at The Second City was even slightly appropriate — I mean, it was dirty and even made us flinch at times, but oh well. Our group of four had a little table in the general admission section, and we were nice and close to the stage. If you ever go, there really isn’t a bad seat in the house. It’s totally hilarious, and I’d recommend this Chicago experience for sure! (Fun fact, one of the six actors was a Florida Gator who happened to be at UF when I was, although I didn’t know him. Small world!)
Overall thoughts on Chicago
I was pleasantly surprised with our trip to Chicago, because I didn’t really know what to expect and ended up really liking the city as well as everything we did. I loved that the city is so walkable, that people are nice and friendly, and I especially liked that the city is very clean. (WAY cleaner than San Francisco, which is sad for this Bay Area girl to say.)
While it was definitely quite cold (I saw snow one day! YAY!!!), we covered a lot of miles on foot each day, one of the days walking more than eight miles total. In addition to the eating and activities above, we also did some shopping on Magnificent Mile (all the expensive stores and some staples like Zara and Topshop too), we went through Navy Pier for the tourist factor, and we really liked exploring Old Town and driving by the Gold Coast neighborhood too. So many things to see in Chicago, it’s clear we need to go back again.
It was great to get away for a few days, catch up with great friends, see new scenery, feel a major chill in the air and eat all the good food! Nice job, Windy City! We’re still full!Stories, pictures and food from a great trip to #Chicago. Check out what @apstyle thinks of #TheWindyCity Click To Tweet
Questions of the day
Have you ever been to Chicago? What did you think?
Do you have any trips coming up? If so, where are you going?