You may have seen on Instagram that I spent last weekend in Chicago with several dear friends. The purpose of our trip was actually to take a class and a test, if you can believe it. My girlfriends and I enjoy win, so we decided last year to create a 2026 goal to learn more about wine varietals and regions through studying and taking a WSET (Wine & Spirits Education Trust) level one test in a different city so that we could make a fun weekend out of it. We are not in the wine industry, but you don't have to be in order to sign up. Our class was a mixture of people in the restaurant industry and regular people like us who just want to be more educated when we look at a wine menu. There are different cities and organizations that offer these tests, and the location that worked out the best for us was Chicago. Twist my arm to visit one of my favorite cities in the summer! Please continue reading to see photos and details for everything I packed and wore (and purchased) on my recent girls' trip to Chicago.
I arrived in Chicago Thursday afternoon to cooler weather than initially expected, but it's the midwest and I have been well trained to bring a rain jacket for potential summer storms. Thursday and Friday included studying for our WSET level one wine test, attending a 2 hour class where we tested our learnings on ANP (appearance, nose, palate) with a selection of wines, and catching up with dear friends over wonderful meals. I was very glad that I took a pair of pants and a jacket for Thursday evening's brisk weather, and we tried a new to me Balkan restaurant called Ambar with a set price for all you can eat plates. The interior decor was beautiful with lots of flowers and I should have taken more photos!
Friday started off cool as well, and I was glad I took a longer skirt for a bit of extra warmth for lunch at Avec and drinks on their rooftop after. As you can see from my hair in these photos, it was a bit windy!
Friday early evening we attended our two hour class and then headed straight to dinner at Rose Mary, one of my favorite restaurants in the city. I wore a thicker weight long sleeve shirtdress for both.
Saturday morning started off cool, but finally warmed up to the sunny and comfortable weather we were expecting. We grabbed coffee and walked up the Magnificent Mile to take our WSET level one test at 9am at one of the hotels. One fun fact about the test is that we were told to bring number 2 pencils to fill out the paper Scantron test and because it is so low-tech, we don't find out if we passed for 4-6 weeks. Wild, right? Regardless, we celebrated completing our tests by visiting the 360 Chicago Observation Deck on the 94th floor of the John Hancock building and toasting our accomplishment with mimosas in the CloudBar. I layered a tank and lightweight merino wool sweater with a pair of tailored shorts and comfortable block heel sandals.
Since the USA is hosting the World Cup this year, there are always games to watch on the weekend and our afternoon consisted of shopping and meeting friends in one of the local sports bars to watch the games. As you can see in these photos, I stopped at Goyard to take a look at the new Musette bag and fell in love with the classic black with black leather version. The size is perfect for everyday wear and travel, and I know I will be wearing this bag on repeat.
Saturday evening we continued celebrating completion of our classes and test with dinner at another one of my favorite restaurants in Chicago: Galit. Galit serves incredible Middle Eastern cuisine, holds one Michelin star, and their tasting menus never disappoint. Since it was warmer Saturday afternoon and evening, I wore a lighter midi dress with a cropped denim jacket and ankle strap sandals.
Sunday morning started with coffee and a walk from our hotel to Millenium Park and the Bean, and then farther down to the Buckingham Fountain in Grant Park (the fountain from the opening scene of the television show Married with Children). I actually had not yet visited this fountain, and it is so pretty! It looks like a fountain that you would find in a park in Paris.
Our flights were around 6:00pm Sunday evening, so we had plenty of time for a leisurely brunch. I stalked reservations at the newest restaurant on the Riverwalk, Naia, a Mediterranean restaurant with stunning light and bright decor and white booths along the river. I was able to snag us a 12:15pm reservation, but when we arrived we were told that there had been a "kitchen emergency" and they might need to close for the day. We were able to grab drinks at the bar, but were so disappointed that we were not able to dine there after all of the work I put in to get us the reservation. Hopefully the next time we visit Chicago we will be able to try again. We still took photos, as you can see the restaurant and location are gorgeous, and for brunch I wore a leopard print camisole with my tailored shorts, ankle strap sandals, cropped denim jacket and my new Goyard Musette bag.
You can also shop the pieces I packed and wore in Chicago below (or similar pieces if the items I am wearing are no longer available):
What are your favorite outfits to pack for a summer girls' weekend? Please don't hesitate to leave me a comment below to let me know. Thank you for visiting my blog today and I hope you have a fabulous week!
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