As I’ve teased on the gram, I recently took a very quick trip to Chicago — I was only there for about 30 hours total, much of which was for a work conference. But I went with two of my gal pals and managed to squeeze in some sightseeing and fun for my first time in the Windy City. What I can for sure say is I DEFINITELY want to go back for more!

While we only had half a day to galavant around town, we packed in all we could.

I thought I’d share what we did, where we went, and what we loved! I’ll also share a little punch list of places I wish I had time to visit. When you are on limited time and are with a group of people, it’s hard to squeeze in all the places you’d personally prioritize, so a second visit is certainly in order. If you have personal recommendations (for local shops and haunts in particular!), I’d really love to hear them — leave them in the comments below!

Okay, so let’s dive in…

Food

Summer House Santa Monica

My friend Emily said this was a must see, and we grabbed an Uber straight from the airport to here. She was right, IT WAS DIVINE. Think one massive and beautifully designed greenhouse with plants all around, an amazing rosé selection, yummy food, and tons of warmth. They have truly captured the essence of feeling like you are at the beach, which was a godsend in the frozen tundra of winter. It was only 11am, but we indulged in booze and food and LIVED OUR BEST DAMN LIVES. I suggest you go do the same.

By the way, I ordered the Butter Lettuce & Herb Salad with Salmon, which was fresh and wonderful, and while the fries were crispy and thin and perfect (I consider myself a fry connoisseur, thank you very much), I LOVE me some tots and regret not ordering the sweet potato tots. #FOODFOMO

We also hit up the coffee and bakery bar on the way out, which is chock full of amazing cookies, rice krispy treats, and unhealthy pastries that hit the spot for our midnight cravings later that night! I’m obviously no where near sorry.

3 Arts Club Cafe at RH

Located inside the beautiful Restoration Hardware showroom, this restaurant felt like a hidden escape to a courtyard in another world. We met a friend of Jessica‘s who lives in Chicago for drinks, which was honestly such a good time! We ordered some bubbly, devoured fries (I told you, I eat them like its my damn job–breakfast, lunch, and dinner friends), and then walked around the showroom (MAYBE a little tipsy–don’t judge!). Their offerings are beautiful, and I hate to say it, but I liked the Chicago showroom more than the Boston one. I’d definitely recommend this place for drinks and browsing!

Somerset

I didn’t grab any photos here, but our friend who lives there took us there and it was beautiful. The food was wonderful, though definitely a little more upscale. I didn’t LOVE what I ordered (maybe because I didn’t order fries?!), but the design of the place was beautiful and the company was really what mattered.

Other places I wanted to try

• The Allis at Soho House
• Doughnut Vault

Shopping

Since time was short, our shopping opportunities were limited…and this is always my favorite activity. As a former shop owner, I relish the details of the retail scene: how stores are setup, their merchandising, who and what they are carrying, etc. Plus I’m a girl and I love shopping and I am a walking cliché and you can just deal with it.

The two main spots we were told to check out were Lincoln Park and someplace nicknamed “The Magnificent Mile.” The latter seemed decked out with all your big commercial flagships, but since I am more interested in the boutiques and local spots, I was told to head to Hyde Park. And off we went!

While there weren’t as many local boutiques as I was hoping, this neighborhood had cute semi-boutique vibes and a small smattering of local shops. The place I dragged everyone into was Serena & Lily, who’s home goods I am constantly bookmarking and getting to see their place IRL was dreamy. I wanted to go home with a ton (the pillows! the accessories! nightstands!), but managed to walk away with a coffee table book knowing I only brought a carry-on bag.

There was a darling apothecary store and a dive-y thrift / vintage store on the same street, but we were running out of time and too cold to venture out too much further on foot with luggage in hand. We popped into Lou & Grey (photo above) across the street, which definitely had some covetable sweat suits (another secret passion of mine, says my husband 🤫) and great small maker collaborators — I was glad we popped in! I grabbed this hair clip and was a total enabler and talked my bestie into getting these earrings, FYI.

That said, I feel like there are A LOT of great shops and locally owned boutiques I have missed and would LOVE to know your favorites for next time I go!

We refueled quickly with some Stumptown coffee in this Amazon bookstore—which is SO WIERD, no? I’ll take my local book stops like Brookline Booksmith, McNally Jackson, or Trident Bookstore any day and definitely need to seek out a good book stop in Chi-town next time I’m there. Of all places, bookstores are my complete weakness and I know I can be a little bit of a snob about it. So I can’t even bring myself to Google a hyperlink to the Amazon IRL bookstore for you…but then again, who the hell do I think I am, I definitely have a Prime membership and USE it. Hypocrite much?

To make matters worse, I bought a coffee there so I AM A CORPORATE SELL OUT. You can join in my communal stoning tomorrow in the back courtyard.

Moving right along…

Stay

While the cool girls may stay at posh ‘bnbs and boutique hotels, we stayed at the Marriot Marquis because it was attached to the conference center of the conference we were attending. Which means we got to walk across a tunnel rather than out in the cold when it came time to work, so no regrets AT ALL.

But I have to say, this Marriot was kind of posh! We had an awesome corner view of the city, there was decent abstract art on the walls, a cute little food court in the lobby with an interior food truck, and their bar was ABSOLUTELY LIT every time I walked by. Business bros were bro-ing hard.

All in all? I’d stay there again, no question.

Other options that look amazing:

• The Gwen Hotel
• Kimpton Hotel Allegro (Kimptons are usually very pet friendly too, so if we go back and take Gazpacho, I’ll probably try to stay here!)
• The Talbott Hotel

Okay, so that is the low down on our 24 hours in Chicago. Did we miss a lot? Absolutely. It’s a big city with a ton to see, do, and eat, and I’m already itching for a second visit (maybe in a warmer month next time!). I mean, look at this nice and awkward photo of us jazzagals! Despite the fact that it looks like all my limbs are missing, I had the best time with these two. Also, I let Jessica borrow my vintage fur coat that night and I’m jealous that it looks better on her than me…such is life.

Let me know what I missed below!