Since this was our third trip to Chicago in the last few years, this weekend was all about finding the hidden gems of the city, and I couldn't have been more thrilled by what we stumbled upon. Before we left I collected every local Chicago shop, restaurant, and hotel recommendation I could and we tried to pop by as many as possible. Ben and I had a specific route planned and an hour-to-hour itinerary. But when we got there, we realized that instead of more busy and more hustle, we wanted our weekend to be about spending quality time with my parents and being surprised by the city. It turns out a little spontaneity can be good for you (yes, even me).
Restaurants, Cafes, and Bakeries
We did make (and stick to) some reservations to restaurants we definitely did not want to miss and every single one of those was a keeper. We had lunch at The Walnut Room on the seventh floor of the State Street Macy's and it was stunning. The room is covered in dark oak paneling and the floor to ceiling windows have a perfect view of the city. Ben and I had some Asiago Chicken that was out of this world. We had a dinner reservation at Harry Caray's Italian Steakhouse that night (which is directly over the torture chambers of some very mean mobster.......we may of explored the basement without asking). Anyway, it was everything it was cracked up to be and my Dad and I may never recover from that insane chocolate cake.
As we were strolling along State Street, we stumbled upon two absolute gems that happen to be right next door. One was The Alliance, a French style bakery full of sweets that might have been just too pretty to eat. I LOVE finding a good bakery, and this one made my heart happy in every way. We kept walking toward the Mag Mile and on absolute impulse I decided I needed a coffee and we popped into Beatrix. This bakery/restaurant/coffee shop/bar somehow made all of those things work together so gracefully. We sat at the bar and had drinks and lattes while we talked the leg off our bartender from Athens, Ohio. If you find yourself there, order a Whistle Pig and a Pumpkin Cream Nitro. You’ll thank me.
The next morning we got up early and took a train to the West Loop for breakfast at The Little Goat. This very glamorous diner was exactly what we needed with warm cranberry muffins, endlessly flowing coffee, and the perfectly warm and chatty atmosphere. Ben and I peeked into the bakery next door to watch the bakers cutting out crosoiants. There was flour floating in the air and barely room to move among the tourists and locals rushing in to snag one of the limited quantity Sunday cinnamon buns.
Just before we headed to our Sunday afternoon football game, we stopped at The Allis @ Soho House. Not only was this my favorite find in Chicago, it may be my favorite find ever. I know I will not do justice to this incredible place, but it was like being transported back in time. The room was full of antique books, the plushest velvet chairs scattered around small wooden tables, couches with trays of crumbly scones, and piles of books. Ben and I sat at the bar and ordered a pot of Bourbon vanilla chai tea. We had the most calming twenty minutes in this beautiful and unexpected little nook.
After lunch in Macy’s we took a stroll through the enormous store and found the Christmas section. I LOVE CHRISTMAS. The Martha Stewart collection was so charming and we probably spent a little too long looking through all the new Christmas dishes.
The other gem on State Street that I mentioned above was P.O.S.H. an enchanting gift shop full of displays of antiques and trinkets from around the world. Ben and I bought an art print of a map of Paris for our living room, but as you can see from the pictures, I would have happily walked away with the whole store.
But in the end the real reason we were in Chicago was to watch Ben’s best friend Harold play for the Chicago Bears. We got to sit three rows over the South inzone in perfect football weather to witness the first Bears victory of the year. It was so fun to watch someone we love so much doing what he loves most in such a huge arena.
Of course that very best part of our trip was all our uninterrupted time with Ben’s and my best couple friends. My mom and dad are kind of the coolest.
Thanks for getting all the way to the bottom of this BIG list! Do you have any favorite off-the-beaten path spots in Chicago. Share them with me in the comments!
Welcome! I'm a brand new wife, first year music teacher, Jesus follower, and am chronically curious about just about everything. Join me as I start off a whole new life.
"I am the Vine, you are the Branches. If you abide in me and I in you, you will bear much fruit; apart from me you can do nothing."