Highlights from my first trip to Chicago

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 …

Chicago by A Lady Goes West

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!

Ashley at Studio Lagree in Chicago by A Lady Goes West

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.

Harvest bowl from Sweetgreen in Chicago by A Lady Goes West

Ashley and Erin at Sweetgreen in Chicago by A Lady Goes West

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!

Ashley and Susie at Dollop in Chicago by A Lady Goes West

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.

Ashley on the Skydeck in Chicago by A Lady Goes West

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!

Skydeck Chicago by A Lady Goes West

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.

Friends at the Bean in Chicago by A Lady Goes West

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.

Pizza by Lou Malnatis in Chicago by A Lady Goes West

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!

Stans Donuts in Chicago by A Lady Goes West

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. 

Brunch at Wildberry Chicago by A Lady Goes West

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.

Goddess in the Bakery treats in Chicago by A Lady Goes West

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.

Dinner at The Vig in Chicago by A Lady Goes West

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.

Ashley and Dave at The Second City in Chicago by A Lady Goes West

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.

Ashley in Chicago by A Lady Goes West

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?



  1. So excited to read this — I’m going to Chicago in May with my brother, his girlfriend and my boyfriend. None of us have been before so I’ve been on the lookout for recommendations!

    Going to Second City is definitely at the top of my list of things I want to do.

    1. Hi Kayla! YES! You should definitely do The Second City and eat in Old Town before the shoe. I think it will be warmer in May, so hopefully you’ll be able to wear a little less clothing than we did hehhe! Have so much fun!!

  2. WOW you covered a lot of ground in a short amount of time! What a recap! So great you got to meet up with blog friends and eat that very odd colored donut. It looks dense and that’s my favorite kind of donut- I don’t like when they are cakey!

    Dane and I definitely want to hit up Chicago sometime. My favorite football team is the Bears, so I gotta REPRESENT!

  3. So glad that you had an incredible time, and even more happy that I got to spend some time with you! Stan’s Donuts is amazing, and I’m glad that some of the more mainstream places showed their best selves! That’s the thing about Chicago–we get so jaded because our city is so awesome. AKA you should come back πŸ˜€

    1. I’m very impressed with your city, that’s for sure! And I would say I’m picky about good food — Chicago rivals SF for sure. SOOO good to see you, friend! πŸ™‚ And yes, I should come back!

  4. This makes me want to go back STAT! My husband is from there and misses it. Putting that doughnut place on my list. And Yes, wish we had a lagree place in WC!!

    1. I would LOVE to be a regular at a Lagree Studio. Seriously, someone needs to open one here! And hubs is from Chicago? Go VISIT soon!! I loved it! Hope you had a nice weekend, Alexa! πŸ™‚

  5. Fun! I visited Chicago for a work conference a few years ago and loved it too. I also ate at Lou Malnati’s and could go for some more right about now. That pistachio donut looks so good.

    My next trip is to Florida next month and after, San Franscisco/Napa, actually! I have never been so really looking forward to it.

      1. Pleasure! I’ll be in the Long Boat Key area to visit my husband’s parents, who recently moved to the area. I would love San Fransisco recs if you have any. πŸ™‚

    1. Hi Megan! It was a great time! Have you ever visited your best friend in Chicago? You should go back! So much to see and do and good food to eat! Blog friends are another major selling point! πŸ™‚

  6. What a great trip! So much fun, delicious food, and how awesome your friends surprised you! I have never been to Chicago, but would totally go just for the pizza, hehe! And so glad you had Sweetgreen, it’s one of my FAVORITE places. I can’t wait for them release their Spring menu.

    1. Hi Patricia! Apparently we have a Sweetgreen in SF, but it’s not close to me. I love it though! I can see why you’re a fan. And hope you make it to explore Chicago one day – you’ll love it!

    1. Hi Julie! I couldn’t believe how clean Chicago was! Way more clean than any other big city I’ve spent time, including SF, where I lived for a few years! Glad you’ve explored Chicago as well. πŸ™‚

    1. No way!! I wonder if you saw the same 105th revue as me or if it was different when you went to Second City. Such a fun place!! What was your favorite restaurant when you were there?

    1. Hi Heather! I totally don’t have serious cold weather clothing, so it was a struggle hehhe! I’d say visiting Chicago in the summer would be awesome, so plan on that! hahah!

  7. I have been to Chicago, but I’ve never done so much exploring; that green donut reminds me of the green donuts I made yesterday! And it’s such a blessing that you got to meet Susie and Erin; that would be one of my goals if I went there again. Those girls are so fun! And it looks like you got in some good workouts too.

    1. Hi Emily! Yes! I love that blogging has helped me to make friends in so many cities! And you made green donuts yourself? Awesome!! πŸ™‚

  8. Wow – this post is a blast from the past!!

    I worked in the Merchandise Mart (just outside of your picture of the river, looks like you might have been standing next to it actually) and lived right next to the water tower downtown on the Magnificent Mile not even four years ago. Then I moved in with my now husband next door to Second City before finally moving to Colorado – interesting fact that one of my favorite bars in the city, Wells on Wells, is right across the street!

    The restaurants you mentioned even resonate so clearly! My husband’s grade school basketball coach was Lou Malnati and my ex boyfriend is a part owner of RPM with G & B, hahah!

    So glad you had so much fun! While I love Colorado more than anything, Chicago will always have a massive, massive piece of my heart (and my whole family, literally, ha!) Thanks for bringing on all the happy thoughts and memories. πŸ™‚

    XO, Jessica

    1. OMG Jess! Wow! That’s awesome that you have some fond memories of your time in Chicago. I loved it there! And wow, sounds like you were a connected lady in the City too! Good job! I totally enjoyed exploring such a clean and welcoming city!

    1. Hi Christina! Thanks for saying hi! I haven’t been to Boston yet either, so I’ll put that on my list! And yes, you should definitely check out Chicago one day! πŸ™‚

    1. It was totally magical that they drove there and showed up to surprise me! I loved it! And I also really enjoyed hanging out with you for a delicious and healthy lunch. πŸ™‚

  9. Well, you definitely visited some of our favorite restaurants and spots in the city. I’m glad to see the cold didn’t prevent you from experiencing everything Chicago offers. The next time you’re back in town or for any of your readers that visit Chicago and want to get some steps in be sure to check us out – Free Chicago Walking Tours – http://www.FreeChicagoWalkingTours.com – we love to have you! 2hr walking tours of Chicago’s best neighborhoods and sites πŸ™‚

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