Cindy's Restaurant Est. 1948.
Coffee. Sweet potato biscuit. Fried egg sandwich. Creole shrimp omelette.
Trying to move to Eagle Rock just to be regulars here.

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Cindy's Restaurant Est. 1948.
Coffee. Sweet potato biscuit. Fried egg sandwich. Creole shrimp omelette.
Trying to move to Eagle Rock just to be regulars here.
Cindy's magical Village Christmas Tree🎄 watch the video above. 🦌
Would you like a bun?
Strap in folks, this is a big one - an excessively detailed account of our Thanksgiving this year. It’s a little self-indulgent, but so is Thanksgiving. And when mixed with gratitude, it seems that can be forgiven.
Since it was so late in my third trimester, Rob and I decided not to travel home for the holidays. We’ve spent Thanksgiving away from home a few times before (like that sort of significant one where we got engaged in New York City), but this one was special, too - our last Thanksgiving as a party of two. So our day started with my large, pregnant self, drinking orange juice out of a champagne glass and watching the parade while Rob took artsy photos of these beauties.
We had reservations for dinner at Cindy’s later that afternoon, but I thought it would be nice for us to have sort of a brunchy snack first to tide us over. Inspired by this recipe for Turkey, Cranberry, and Brie Rolls by Ciara Attwell, I planned for us to have a sausage, cranberry, and goat cheese version. I admit, I started to make them myself, but after getting frustrated while rolling out the puff pastry, Rob took over and returned me to the couch with my orange juice and my parade. Smart.
So it was Rob who (mostly) fixed and documented these sausage and cranberry rolls, and here’s how he/we did it:
Ingredients: 2 teaspoons olive oil 1 package mild Italian sausage 1 can cranberry sauce 4 oz goat cheese 1 package puff pastry (2 sheets) Green onions
Directions:
Thaw the puff pastry dough in the refrigerator overnight. When you’re ready to make the rolls, preheat the oven to 350 degrees. Heat the olive oil in a large skillet over medium high heat. Form sausage into 18 small meatballs and fry until golden brown on all sides. Set aside to cool. If you’re me, roll out the puff pastry dough into a large square; cut each sheet into nine equal squares (18 squares total). Brush each square with cranberry sauce and add a meatball, a small lump of goat cheese, and some snipped green onions to the center. Fold the corners to the center, invert, and place seam-side-down on a baking sheet. If you’re Rob, roll out each pastry sheet into a wide rectangle. Brush with cranberry sauce and equally space (about 1/2 inch between) nine meatballs, lumps of goat cheese, and snipped green onions across the lower half of the pastry. Fold the top of the pastry down to the bottom and press it gently over the filling; then cut into nine squares and place on a baking sheet. Bake in the oven for 30-40 minutes or until the puff pastry is golden brown and flaky. Serve with remaining cranberry sauce.
While these little Wellingtons couldn’t help but be delicious with those flavors, they were a much bigger pain to make and took far longer to both make and cook than I had anticipated. I wished I’d made them the night before or decided to make something easier - I think the parade was over by the time we finally ate, and then we had to hustle to get all cleaned up for our fancy dinner out.
Thankfully, at 36 weeks pregnant, it’s almost impossible to spoil your dinner.
Like I mentioned before, we had reservations at Cindy’s, which is the rooftop bar of the Chicago Athletic Association. We had been to Cindy’s together once in the past, for a drink on my 28th birthday before dinner in the Cherry Circle Room. I seem to remember a bottle of Miller High Life costing over $10, so I didn’t think we’d ever be able to afford a meal there. But as we shopped for places to have our Thanksgiving dinner, we found Cindy’s prix fixe to be one of the most modestly priced - only $60 for two people.
We thought it would be slammed when we arrived around 2pm, but it was strangely calm - the tables weren’t full, and the staff seemed welcoming and relaxed. I hadn’t anticipated what a nice surprise that would be; I was expecting to be churned in and out by a harried staff looking to turn tables on a busy food holiday. Instead, it felt like we could take our time and enjoy both the food and the beautiful space.
We could have ordered a la carte, but despite going out to a restaurant for Thanksgiving, I’m a traditionalist and have got to have that turkey dinner. They were serving a “family style” dinner of shaved turkey breast, braised turkey leg and thigh, cranberry aigre doux, cast-iron cornbread apple sage stuffing, whipped potatoes, and glazed haricot verts. (Sadly, no bun for Planes, Trains, and Automobiles fans.)
By family style, they meant “all on one plate,” and I’d be lying if I said Rob and I were a little disappointed when we saw it land on our table. This is a $60 dinner for two??
Okay, so it didn’t look like much food on the plate, but once we divvied it up, it turned out to be a reasonable portion of food. Which was still a little disappointing, because who eats a reasonable portion of food on Thanksgiving? Especially when pregnant? You may also notice that there’s no cranberry sauce on the plate - they forgot to give it to us at first, and I couldn’t fathom eating this meal without dipping every odd bite in the stuff. So we had to wait a few minutes for our waitress to return with it before digging in; it turned out to not be great cranberry sauce, but it was better than no cranberry sauce.
Overall, what this dinner lacked in volume, it made up for in flavor. The turkey breast was outstanding - the skin was perfectly seasoned, and the meat was amazingly moist. Shocking all, I preferred it to the dark meat, which was a little dry and stringy somehow and could have used more gravy. The stuffing was delicious with a very pronounced cornbread flavor, and the silky smooth mashed potatoes may very well have been half butter. The haricots verts (all ten of them...why not serve more??) were snappy and fresh and totally didn’t need the French-fried onions on top - I get the nod to the casserole, but it wasn’t a casserole and didn’t seem to match.
When we finished our delicious dinner, we moseyed out to the rooftop deck - it was a beautiful fall day in Chicago, helped along by some cozy heat lamps and a stunning view of Michigan Avenue. And the Bean, getting beamed up into space.
We stayed outside and relaxed for a while; I ordered coffee and Rob finished his wine while we took photos and enjoyed the scenery.
And when we finally decided it was time to go, we descended the 13 floors of the hotel as I clutched my real/food baby.
We weren’t quite ready to call it a day at this point; it wasn’t yet 4:00, and it was so nice outside that we decided to walk around downtown a bit.
This jaunt took us down the Magnificent Mile, where we enjoyed some moments of tourism in beautiful Chicago. I recommend this type of activity, wherever you live - it’s nice to take in your surroundings without some other purpose or errand.
I say that, but at this stage in my pregnancy, I was having hip pain like I’ve never had before in my life. So it may not have actually been our best idea to take such a long walk. But I was having such a good time, it seemed worth it.
The goal was to make it to the historic water tower before heading home, and my lamentable hips managed to make the journey. By that time, it was getting dusky and the Christmas lights were coming on throughout Michigan Avenue. Dreamy!
When we finally got home from our cosmopolitan holiday, things got a little more low brow, from the clothes, to the food, to the photography. We got into sweats, ordered pizza (Dominos is my guilty pleasure), and were too lazy to go get the Nikon, so we documented it with our phones. My favorite kind of downward spiral!
And we ended the night with a movie on the couch and this sweet nugget, who wouldn’t be an only child for much longer.
What a good day this was, sort of a private holiday for the two of us. Though it didn’t have the waist-expanding power of a traditional Thanksgiving dinner, we really enjoyed our meal at Cindy’s, both in the quality of the food and just the sort of special, classy experience we had there. It was a beautiful day to be out in the city and to be cozy on the couch at night. We would have loved to have been with our families this Thanksgiving, but if we couldn’t be home, I can’t imagine a way I would have rather spent it.
Caroline
Cindy’s Diner
Chicago