Chicago
I lived in Chicago for almost twenty-five years and developed a short list of favorite coffee shops, bakeries, and restaurants. These are the spots our family looks forward to going back to when we visit and the recommendations I share with friends!
Chicago Skyline from the Wendella Sunset Architecture Tour, July 2025
Andersonville
m Henry - I love jorge’s black bean cakes, fannie’s killer fried egg sandwich, and sharing the bliss cakes and my husband loves the rustic quiche which comes with a lovely side salad.
Parson’s Chicken & Fish* - I love the burger - one of my favorites anywhere! If you like pickles, be sure to get a pickle drink of some kind. The slushies are also delicious on a hot day.
Anteprima - I love everything I’ve ever had here! It is nice to go with a friend and share starters, a salad, pasta, and dessert. Favorites: octupus, orecchiette, lemon panna cotta.
Lost Larson - I love a yummy croissant - try butter, chocolate, or chocolate hazlenut. You can’t go wrong with whatever speaks to you from the case!
First Slice* - I love their peanut butter chocolate pie so much that I will bring it home on the plane if I have flown! Our family all love it so much that we have to sometimes say “forks down” so there is equal opportunity eating. I also love the Latin Hip Hop Salad with chicken and they make a good latte!
Fiya - I love the hummus and Fiya salad but there are tons of great options!
Coffee Studio - I love their chai latte.
La Colombe - There are many locations around Chicago and they have excellent coffee. I love getting a latte!
boutique: Winifred Grace - I love everything about the shop! Winnie is wonderful and warm as is her staff. You can shop online even when you aren’t in the city. My favorite shoes were purchases through WG, my locket with my son’s photo, and several special pieces! They also offer permanent jewelry and I made a very specific intention with mine which served as a reminder to me leading to reprioritizing some important things in my life.
Rogers Park / Edgewater
Evanston
Hewn*
Logan Square
Lincoln Square & Ravenswood
Burbs/North Shore
Pequod’s Pizza* (Morton Grove)
Three Tarts (Northfield)
Other To Dos
Wendella Architectural Tour - I love the sunset tour. Beautiful views of the city and it is always fun and educational.
Lake Michigan - I love the beauty of the lake and there are many ways to enjoy it depending on where you are in the city. We lived far noth in Chicago so spent a lot of time in Evanston and the beaches and lakefront parks are lovely. Grab a coffee or lunch and enjoy the view! Of course, there is a lakefront path all along the city where people love to walk, run, and bike!
*Multiple locations
