Chicago!
a list of everything I discovered and loved this June ( part one )
I just returned from a week in Chicago where I had the absolute best time celebrating my birthday, eating, exploring and walking our way through the city. Previous to this trip I have spent approximately a total of 12 hours in this city - but have been smitten and been dying for the chance to come back and explore ever since!
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I really can’t explain why, but I love Chicago. Maybe I lived here in a past life, but I felt at ease, comfortable and so happy to be there. The people are refreshingly nice, and there is so much good food to eat, and places to explore. And the train! Public transportation in Seattle is not my favorite - but the trains in Chicago are so fun. I felt like I was in adult Disneyland the whole time, almost surreal how warm, beautiful and vibrant the city is at all times.
This trip served a number of missions: ( 1 ) find cute shops to carry my Beanies this winter ( 2 ) get my bearings of where the Chicago Renegade September market happens and of course ( 3 ) celebrate my birthday with a fun getaway and vacation.
We opted to stay at an AirBnb in a neighborhood vs. a hotel in the Loop so we could fully immerse ourselves in the Chicago life. I highly recommend going this route - as we had such a warm, cozy and inviting stay with ample recommendations from our host. We stayed in Bucktown which proved to be the perfect starting point to explore. Damen street was full of great shops and places to eat - and we were only a 15 minute walk to the train which took us to other places and neighborhoods we wanted to explore. We literally walked EVERYWHERE , logging a record 13 miles on day one in 93 degree heat - and only took one uber home late at night after our trip to the Weiner Circle for a true Chicago dog.
It felt so nice to have no schedule or itinerary, and to just wander and explore to our hearts content. We had many lovely recommendations from locals as well as found ourselves a handful of gems all on our own. I love the feeling of walking and exploring new cities, and want to carry this mindset back home with me as a way to remember to always explore your own backyard. I feel refreshed and inspired for summer - but first I want to share my very favorite finds with you!
COFFEE SHOPS
My favorite in Bucktown was TRUCE - a clever coffee & cocktail concept that serves all day coffee, and turns into a cocktail bar at night. This is the concept I have wanted to see in Seattle forever ( does it exist here? ) - it was beautifully designed and their “Second Date” latte was my favorite.
not to miss - Red June cafe ( fresh smoothies! ) and Fox Trot Market ( a cute Chicago chain that is like a fancy upscale 7-11 bodega )
BARS
I had two favorite bars - the first was The Charleston a very cool historic neighborhood bar with an amazing interior and locals vibe. This was just around the corner from our AirBnb and served up music on vinyl and a fun ( digital ) photobooth in the back. The second was Estereo - a bar we stumbled upon after walking through Palmer Square / Lincoln Park in a daze from the heat. It had a beautiful interior, unique bar and a full wall of windows open to the sidewalk. It had an extensive list of Mezcal and some yummy N/A drinks as well. This is exactly the type of bar I want to find in any city - and I was so glad we found this by happy accident.
not to miss - For Chicago Fire fans ( me, hi it’s me ) , Lottie’s Pub is located in Bucktown and is where they film scenes for Molly’s. We had to pop-in just to see it!
EAT - LUNCH
My favorite lunch was recommended to us from Emma, owner of The Sunday Standard. We grabbed a sandwich from Lardon to-go and walked over to Palmer Square to eat in the shady grass. I will forever be dreaming of this sandwich ( we got the classic Italian - and it came with made in-house chips and pickles ), and I must go back next time I’m in town for their happy hour and/or dinner tasting menu. I’m still drooling just thinking about this sandwich!!
not to miss - we grabbed a much-needed late lunch from Big Star one day - the nachos and fresh watermelon agua fresca were stellar!
EAT - DINNER
Dinner is where this trip really shined - and my favorite dinner(s) were the two ( ha! ) we had on my actual birthday.
First was our early dinner at PIZZ’AMICI for true tavern style pizza. We just happened to be walking around West Town right before 4pm and what we didn’t know is that they typically require reservations and the only way to hope you snag a table is to get there at open, so we felt like we won the lotto after hearing this because the pizza and salad were ABSOLUTE PERFECTION. I will be dreaming of this pizza forever. It was thin, crispy and insane - plus the ceasar salad was probably the best ceasar salad I can ever remember having? In my whole life?!
Our second dinner ( my birthday dinner ) was recommended to us by our host. This story is actually quite special - and I can’t believe we got a table on this night. We went to Monteverde in the West Loop - however what we didn’t know is that Chef Bailey ( the CDC of Monteverde ) was on this season of Top Chef, and the night we went was the night of the finale, in which she was in the final 3 chefs ( what?! ). Reservations would have been impossible, so we took our chances, walked in and got a spot at the bar without a wait. How? I still can’t believe it! We had a front row view of the kitchen hard at work, and a TV to our left which was airing the Top Chef finale. It felt all so magical.
Our dinner was absolutely delish - we had the June special pasta with a single meatball which was cooked to absolute perfection ( it was soft and fluffy somehow? ).
not to miss - a late night Chicago-style hotdog ( and french fries ) from the Weiner Circle! Be prepared to get roasted - it’s all part of the experience * wink.
This post is officially getting long - so come back for Part Two where I share my favorite vintage, thrift and small boutiques!
Have you been to any of these spots? Do you have a favorite Chicago spot I should add to my list? Join the conversation below, or send me an email with your notes!
Michelle Moore is a Seattle-based creative, vintage curator, photographer, writer and educator. You can catch her at an up-coming pop-up, swing by on a night she’s hosting at the restaurant in Ballard, order one of her hand-knit Beanies, or hire her to host & plan your next event.
connecting you with good clothes + good people.