Welcome to The Weekly Rundown: Chicago edition! This past weekend, we made our way to Chicago for a quick (somewhat last minute!) trip with friends. Having just finished season 3 of The Bear, the trip’s itinerary was mostly food and drink driven, peppered with fun activities — including a run-in with my cousin and her son who were also in town! Somehow 80 degree weather felt like a welcomed relief from the South’s brutal temperatures, but we definitely didn’t need the extra layers for evenings like we’d planned. Sharing a recap in the form of Weekly Rundown below — things we ate, drank, saw, wore, etc. (Disclaimer: not a guide! This was my first trip to Chicago, so I’m definitely not an expert … these are just things we loved.)
WEARING
During the day, I was really happy to have my solid white New Balance 9060s. They were the perfect chunky sneaker to add some stylish interest and were incredibly comfortable for walking around all day.
I found two new dresses for this trip — a black Cos midi dress and a linen maxi from & Other Stories (on sale and available in lavender too!). I’m excited about having both of these staples in my closet for nights out or for work, topped with a denim jacket.
I posted these last week, but my linen Gap shorts and perfectwhitetee tank were the ideal outfit for first day, except for the wrinkles acquired by linen, of course. On Saturday, we wore workout clothes (favorite lululemon tank and shorts) for bike riding. I was really glad we did a casual day!
I wore this strapless top in white (on sale!) one evening and actually packed the same one in black. I’m seeing so much strapless lately! These are easy and can be dressed up or down.
SHOPPING
I wish we had done a little more research on shopping ahead of time! The one spot we saw on multiple lists that was a fun stop-in was P.O.S.H. It’s downtown, so easily accessible, and it was filled with so many special items. A mix of vintage silver, cookbooks, home accessories, gardening tools, specialty food items and more. I felt like I did 10 circles around the shop and still didn’t see it all. Left with a (very early) Christmas gift for my mom and two tiny salt cellars for our tabletop. Looks like you can shop online which is fun!
EATING
Like I said above, we did so much research about where to eat in town. And somehow we left without a slice of pizza! These are the spots I would most highly recommend (and what to order, where necessary).
Kasama (breakfast; East Ukrainian Village): This might have been our favorite (and most anticipated) spot. In season 2 of The Bear, Sydney orders a breakfast sandwich here, and we saw it on just about every recommendation list. We arrived a little before nine, and the line was down the block. Luckily, someone had made the recommendation to order online right when they open! We did, and our order was up in 30 minutes. Most of the group ordered the breakfast sandwich with longanisa (a Filipino sausage), egg, cheese and hashbrown. I skipped the sausage on mine and also had a black sesame iced latte. The sandwich is so simple — there’s no sauce, just the listed ingredients — but it is so flavorful. We strongly considered going back for more on our last day!
Daisies (dinner; Logan Square): On Thursday night, we went to Daisies for pasta, and we couldn’t have walked away happier. Each of us had a different favorite dish, which I think means everything was fantastic. A few standouts: house made ruffles and onion dip, potted carrots, spring onion toast, raviolo, mushroom gnocchi, pappardelle, and VERY importantly for dessert, the malted cookie dough gelato. One of my personal favorite bites from the trip!
Maxwells Trading (dinner; West Loop): For dinner on Saturday, we had a late reservation at Maxwells Trading which served some of the most consistently great food of the weekend. We had positive things to say about every dish, but the softshell crab, scallion griddle bread, sweet potatoes and clay pot rice were definitely the favorites. Service was a little odd, but we’d definitely go back anyway.
Portillo’s (lunch; multiple locations): Everywhere we went, RJ asked where to find the best Chicago beef. Every single response was different, so we finally landed on Portillo’s so that we could try a few different Chicago classics. While it’s probably a bit touristy, we absolutely loved it. Favorites here: the Chicago beef with hot peppers and the Chicago hot dog.
DRINKING
Miru (for the view; Downtown): We had beautiful weather on Friday — sunny and warm but not too hot. After our architectural tour, we headed to the St. Regis restaurant Miru for a drink on their terrace. You can’t beat the view up there, and the whole experience was just so pleasant.
Kumiko (unique experience; West Loop): Before dinner on Friday evening, we stumbled into Kumiko. We were lucky they had a table leaving just as we walked through the doors. We had read good things but didn’t know we were in for such a treat. The service was unparalleled. The drink menu was thoughtful and unique, and we left talking about the pickled turnips of all things. It wasn’t inexpensive, but this topped our list of favorite experiences of our entire weekend.
Bisous (cozy atmosphere; Fulton Market): A few waiters had recommended this newer spot in Fulton Market for pre-dinner drinks. A Parisian-inspired cocktail bar that boasted a martini menu, we were very happy. Always love a round booth for a group, too.
Cindy’s (great view; Loop): Cindy’s is known for its view of Lake Michigan and Millennium Park. While the cocktails weren’t anything too special, the view was absolutely worth the visit — especially for our first night. The rooftop was so enjoyable and not nearly as crowded as we expected for a popular tourist spot.
DOING
Architectural Tour: Every. single. person. told us we couldn’t miss the architectural tour, and now I know why! We did this first thing on Friday, and it was a great way to see and learn about the city. The weather was absolutely perfect for a boat tour, and our guide was entertaining and knowledgeable, to say the least. It really is a can’t-miss!
Bikes by the Lake: We rented bikes on Saturday and hit the Lakefront Trail. Admittedly, I was a little nervous as I haven’t ridden a non-stationary bike in years, but this was so much fun. We all loved moving around for a while, and the views of the city were incredible.
Flyover: Okay, I’m halfway recommending this. In an effort to fill up some time with activities (instead of shopping/eating), we came across Flyover. It’s a simulation of flying over Chicago (similar to Disney’s Soarin’ if you’re familiar). It’s located on Navy Pier which was packed with visitors and kids and was quite chaotic! I mean, the ride couldn’t be more of a touristy experience and dealing with the pier was a lot … but we loved it. We laughed so hard the entire time and were glad we did it in the end. Proceed with caution 😂
The Bean and Millennium Park: You have to! The Bean was also a little packed, but of course we had to stop by. The park has so much to see and do, and we all wished we’d spent more time wandering around. We were planning to visit the Art Institute and also regret that somehow we ran out of time for that too. Next time!
This edition of Weekly Rundown is a little longer than usual! You might need to click “View entire message” or view in the Substack app or website (annieaxe.substack.com) to see all of the photos below.
Whew! Such a fun trip — truly so sad it’s over. See you back here next week where I’m excited to be introducing a fun new section to eudaemonic!
xx, Annie
Nice! I work with an agency in Chicago now and always visit P.O.S.H. when I'm in town. Adding some of your restaurant recs to my list for next time!
You did a great job hitting a lot of local favorites! Glad you had a good trip!