Chicago Recs

If you're in my Kate's Kittens reader group, you might know about my recommendations post. But if not, I figured I'd share a few of my favorite places, restaurants, and things to do.

I've also mentioned if a rec is used in one of my Chicago-set books.  

Deep-dish. So I'm not a huge fan but people who come to visit always want to do this. We usually take them to Gino's East. There might be lines and it's pretty loud. Not a lot of choice on the pizza, but if you're doing one deep-dish experience, this would be my rec. They have an unusual corn-based crust which sets it apart from other deep-dish. It's also very yellow! I hear good things about the deep-dish at Uno, though they make you order *while in line* which smacks of f-you, to be honest.

Recently, I tried Pequod's Pizza Chicago for the first time and LOVED it. They caramelize the crust and the 7-inch personal size is perfect for one. It's in west Lincoln Park, so take an Uber/Lyft from downtown or Mag Mile.

Restaurants: If you're visiting, you're probably staying somewhere downtown or along the Mag Mile. Lots of great restaurants, but these would be my picks. Some I'm picking more for the vibe than the food:

  • Purple Pig ($$). Great small plates; they moved location recently so it's a bit bigger, slicker, and more expensive. Still good.

  • The Gage ($$$). Great cocktails, very cool vibe. Near the Art Institute, so might make a good pre- or post-gallery visit. Also has a nice brunch.

  • River Roast ($$$). There are a few riverside spots in Chicago but this one is my favorite. If visiting during warm weather (and I don't recommend you come at any other time!), try to wait it out for a table outside but even if you can't get one, the dining room is really nice and has lovely views. Fabulous cocktails, and if you're a meatlover, they do these amazing group-share roasts.

  • City Winery on the Riverwalk ($$). Another nice riverside spot and as the name implies, great for wine. They have domes you can reserve in advance which are great for groups.

  • Piccolo Sogno ($$$). Great Italian in a gorgeous alfresco courtyard. A bit pricey but really good. Not really walkable from Mag Mile/Loop. (I based DeLuca's in the Hot in the Kitchen series on this place; Eli and Alex in Playing with Fire have their post-Blackhawks game dinner at DeLuca's)

  • Sepia ($$$). Gorgeous dining room set in old Printers Row building. Another amazing cocktail place. (I based Brady's restaurant, Smith & Jones, on this place. Featured in all the Hot in Chicago books and a couple of Rebels books.)

  • Gaijin ($$). One-of-a-kind Japanese food. Not sushi, but a special kind of filled cabbage omelette-pancake with meat, fish, or veg toppings. Check out the website for better descriptions and videos. It sounds weird but it's one of the best meals you'll ever have and it won't break the bank. This is in Fulton Market, which is the west Loop, a cab ride away from the Mag Mile/downtown.

  • Gayle's best ever grilled cheese (at MCA farmers' market on Tuesdays, IIRC; maybe at other farmers' markets? Featured in Sparking the Fire; Wyatt and Molly walk the market and have grilled cheese samples.)

Afternoon tea: so this might seem like a weird, old-lady rec but I think these make great group outings and Chicago has a few afternoon teas that are really lovely. If you time these right, it would be a good late lunch before you hit the cocktail hour. My faves are the Peninsula and the Drake. (I used the Drake in the Ferris Beuller's Day Off homage in Hooked on You.) The Langham is overpriced and overrated.

Cocktails: You can buy a really expensive cocktail and get a fabulous view of the city at the Signature Lounge on the 96th floor of the Hancock (complete with spiders on the outside windows! How do they get so high?). Might be a better option than paying for the Observation Deck which is pretty much the same view. The Signature Room is the restaurant on the 95th floor - don't eat here unless you have unlimited wads of folding money! (Kinsey and Madison had dinner in the Signature Room in Flirting with Fire.)

There are also a couple of nice rooftop bars: Cindy's and one in the Wit hotel are the ones that come to mind. (In fact while in the Wit bar, I had the idea for In Skates Trouble as I watched the balconies in the buildings across from the bar.) The Raised Rooftop at Renaissance Hotel is an outdoor bar with a great view of the Chicago River. I've been in December and March when they use fire pits, and it was manageable temp-wise. So not a terrible way to spend 30 minutes and your hard-earned cash!

If you're willing to venture outside of the Loop/Mag Mile: you could take a train ride or an Uber to the Lincoln Square neighborhood which has some of my fave neighborhood restaurants. The ones I'd rec here are:

  • Due Lire (Italian)

  • Bistro Compagne (French)

  • Gather (bit of everything)

  • Spacca Napoli (Neopolitan pizza and the best burrata in the city)

  • Sweet Mandy B's (best cupcakes in Chicago)

  • Or do a bar crawl in the Wrigley field area

  • Or go for Vietnamese food on Argyle - Cafe Huong is amazing value

More recs in other Chicago neighborhoods - take an Uber/Lyft or train:

  • Superdawg Drive-in (hot dogs)

  • Chicago Pizza & Oven Grinder (featured in Illegally Yours - Lucas takes Trinity and the soccer team here)

  • Ann Sather's (cinnamon rolls - I try to mention these once per book!)

  • Fudge Pot (chocolatier)

  • Portillo's (hot dogs, assorted locations)

  • Gus's World Famous Fried Chicken

  • Molly's Cupcakes

  • Maxwell St. Polish

  • Burger Bar (several locations, also recommended for gluten-free)

Things to do: I'm not as plugged in on things to do in Chicago as I once was because I'm basically a hermit in my old age.

  • the Architecture Boat tour: The best way to see the city buildings. If it's cold, I wouldn't do it, though, because on the boat, it's really cold

  • the Bean/Millennium Park/Maggie Daley Park: these are nice walkaround places (Shane and Cara in All Fired Up bonded beneath the Bean.)

  • Art Institute and Museum of Contemporary Art: these would be my favorite art galleries, esp. the AI. AI also has a nice restaurant.

  • Hottix: Check this to see if there are any half-price shows.

  • Kind of unusual, but I always rec this: Chicago Magic Lounge. This is a train ride/Uber ride away from downtown and a really cool experience. Even if you think magic is for kids, you will enjoy this. It's old-timey and totally off the beaten path. You can also visit the bar and see close-up magic if you don't have show tickets. Drinks are pricey but your bartender is doing tricks! There is another magic show in the Loop at the Palmer House - Chicago Magic Parlor. It's good but the Lounge is better.