What I Learned in the Chicago Area
Indie Bookstores, Restaurants, and More
Last weekend, I got to explore the North Shore of Chicago. I wandered into suburbs I’d never been to where the residents had been there for generations.
Kyle and I had dinner with locals in Highland Park where, I found out, two years ago, a terrorist had started shooting into the crowd during their beloved July 4th parade, murdering neighbors and causing residents to grab their kids and run for their lives. Nice Jewish families. A grandmother with her heel blown off who hadn’t realized it until she made it to safety and took off her shoe. Right there! In their town. The shock lingered.
We drove through Evanston, home of Northwestern. I expected an adorable college town. Instead, we decamped quickly and decided to stay downtown instead. (The Graduate Hotel there? Not the best. I’ll take the Tucson Graduate any day.)
Lake Forest Bookstore was elegant, beautiful. A book we published, I See You’ve Called in Dead by John Kenney, was perched above the check-out counter, listed as their #4 bestseller. Local stores had apparently been replaced by luxurious brands: Lululemon. Williams-Sonoma.
“You’ve got to drive down Sheridan Road,” Anne, the bookseller said. “You’ll see all the country clubs. The real North Shore.”
“Will do!”
Kyle and I left the bookstore.
“You were talking like you have any idea where Sheridan Road is,” he said, as I started laughing.
“Google Maps!”
We drove through the surrounding areas, dotted by stately homes and manicured lawns, past other towns like Glencoe and Winnetka, where we stopped at Serena & Lily, got cherry chocolate chip ice cream at Graeter’s, and hunted down Frankie’s on the Park, a second outpost of the Santa Monica store I used to buy most my girls’ favorite clothes from. We also popped into the Book Stall, a much larger footprint, with all types of fabulous reads and merch.
The Book Bin had closed early but luckily sold all the books at the event for World ORT at which I spoke Sunday. I missed Bookends and Beginnings in Evanston (shoot!) and the Secret Garden Books in Highland Park.
Of course, we spent the morning at the quaint cottage that housed Matchmaker Bookstore, new to the area. The hunter green walls, floral ceiling wallpaper, and maroon accents made it feel comfy and warm. Our Petite Retreat at Matchmaker was so much fun! Photos here. Video here.
That night, we ate in Deerfield at Rosebud (get the pappardelle!) and braved 90 minutes of traffic back downtown. (Also check out Shanghai Terrace at the Peninsula.)
The next morning, in honor of World ORT’s dedication to education with Jewish values, I shared a few things I’d learned about myself, others, and perhaps those in the audience. Here are a few of them: (full speech recording here)
When I perceive something to be unfair I speak up.
I learned to notice the burgeoning signs of antisemitism in Hebrew school and to speak out about them. But I learned that doing everything I’m supposed to do doesn’t always work.
I’ve learned to accept that I have zero spatial ability and will walk into anyone.
I’ve learned you can always change your life and it starts with one small step. No matter how stuck you feel, you can change things.
Mostly, I’ve learned that the Chicago-area people have enormous pride in their communities — as well they should. I hope to come back soon.






