How do you know you’ve made a city your own? When you can quickly rattle off a list of go-to spots that you’ve become a regular at. There are a few essentials that I seek out in every city I go to, ranging from places to eat and drink to places to bike and dance. I recently hit my two year anniversary as a Chicago dweller, and it was made bittersweet by the fact that I was actually moving out of the city. While excited for new adventures, I was sad to say goodbye to my favorite haunts, many of which I discovered within my first few months in Chicago.
Here are my Chicago essentials, spots that I can’t wait to visit again when I’m back.
Breakfast/Lunch/Pastries: Toni Patisserie
Toni Patisserie is a slice of old Europe just off of Michigan Avenue near the Art Institute. It’s bright, airy, and the dessert cases are always packed with fresh pastries and cakes. Whenever possible, I would arrange to have my coffee meet-ups here, and it's the place that I would always take visiting friends to for brunch -- in avoidance of the River North the brunch scene. In addition to its homemade soups, sandwiches, salads, and crepes, Toni has a very excellent wine happy hour. In fact, its happy hour might be one of Toni's best kept secrets, and I would see only a few regulars in there at 5 o'clock eating Paris-Brest and drinking rosé. I should also mention that Toni has some of the best wine I’ve found in Chicago. Kermit Lynch’s bottles dominate the selection.
Cheap and Cheerful: Taqueria El Milagro (1923 S Blue Island Ave)
About as hole in the wall as it can get for tacos. The kitchen serves up classics like pork and pineapple, and chicken with tomatillo salsa, but for those eaters more adventurous than I am, you can find truly authentic fillings that will never appear on a menu at Taco Bell. Highly recommended before a night at Punch House.
Casual: Bite Cafe
You’re unlikely to find this place unless you go looking for it. It’s on a stretch of western Chicago near Wicker Park that isn’t close to a train, and so it doesn’t get anything close to the foot-traffic that Milwaukee Ave does. Bite specializes in American-European bistro cuisine and will always have a curry special and fresh seafood on the menu. I usually get the short-rib gnocchi or grilled salmon. The food’s delicious, the space is easy going and totally unpretentious, and it’s BYOB. Hello, Friday night.
Breakfast & Brunch: Lula Cafe
One of my favorite things about grad school was that my schedule was all over the place, meaning that I didn't really have a schedule apart from my classes. That meant that I could take myself out for breakfast during the week while most people were at work. I would often wander to Lula Cafe in Logan Square, either with a friend or just myself, for a relaxed morning enjoying Lula's amazing breakfasts like lavender biscuits and ginger brioche french toast.
Located on Randolph Street (aka West Loop's "main street"), Salero is a breath of fresh air among the chaos and long waits of West Loop's trendy eateries. From its beautifully simple decor -- exposed stone, wood beams -- to its chilled out playlist, Salero demonstrates unpretentious classiness in its embrace of Basque country cooking and design. The menu is packed with tapas as well as entrees (for people like me who don't always like sharing their dinner) including seafoods and paella. Follow the servers' recommendations when you order, and make sure to include a glass or two of Spanish sherry.
Dessert: Bang Bang Pie
It’s hard to call favorites when it comes to desserts in Chicago, but this place is a clear winner. Bang Bang regularly rotates its pie offerings and everything is seasonal, so the menu never gets stale. Some recent favorites included strawberry and rhubarb cream, and "Lemon Bar Berry" that included lavender sea salt.
Cocktails: Broken Shaker & The Violet Hour
Tucked in the very back of the Freehand hotel and decorated like a Wes Anderson set, Broken Shaker is a gem in River North. It’s literally the only bar in that area that I take people to. Every drink is some bizarre take on its classic predecessor, and the Bengali Old Fashioned and Viking Funeral are just a few examples. Bonus points for good music and low lighting.
The Violet Hour, in Wicker Park, also won me over with its playlists and insanely imaginative drinks like "Lust By The Bonfire" (tequila and strawberry-infused Dolin Blanc). Whereas Broken Shaker feels like a casual, local spot, Violet Hour's mysterious location (it's hidden behind an unmarked door) and ornate decor makes every visit there feel like an occasion. I've gone with big groups where we spent hours trying different drinks, and I've gone with just one or two people and sipped on a single drink and enjoyed disappearing into a room without cell reception for an hour or so.
Cheap and Cheerful: The Whistler
There are few places where you can find a cocktail for $8. And there are fewer still where those cocktails are called "Wild Cats" and involve chai-infused bourbon. I give you, the Whistler. On a bustling street in Logan Square it's the kind of place where you can spend a night sloshing through Wild Cats and dancing to jazz or a DJ set, or you can hide on their garden patio with friends and just catch up and lounge. Monday - Saturday, for whatever mood you're in, the Whistler has you covered.
Total Dives: Rossi's and Richard's
I don't want to say too much in order to allow Rossi's and Richard's the chance to truly shock and awe, but if you're looking for a real Chicago dive bar, you can't go wrong with either. Last I checked, Rossi's opens at 7am and has some sort of eggs and Jameson special -- unclear where the kitchen for cooking said eggs is -- and Richard's clientele is straight out of central casting for the Sopranos. Did I mention that it's the last bar in Chicago where people can smoke inside and buy cigarettes behind the counter? Also available are hard boiled eggs for 50 cents and $3 drafts. Bring cash. And a shirt you'll never want to wear again.
MUSIC AND DANCING
SmartBar and Punch House are the best places to dance in Chicago. Chicago and Detroit house music are staples at both, but both spots regularly rotate a diverse range of music from all over the world. SmartBar leans towards electronica and disco, while Punch House will have everything from Italo Disco and hip hop to a Morrisey tribute night.
For concerts, Thalia Hall, Aragon Ballroom, and Concord Music Hall pull in acts like the xx, the National, and London Grammar. The Old Town Folk Music School is a hidden gem, with lesser known but no less loved artists like Agnes Obel, who I saw there in the spring.
Book Store: Pilsen Community Books
Used and new books with an emphasis on fiction and art. I sometimes get overwhelmed in used bookstores because there’s so much going on, but this shop is really well-organized and doesn't smell like a basement. My last purchase was Madame Bovary and a German cookbook. My friend left with about 30 art books.
Record Stores: Gramophone and the Dusty Groove
I had to go with both because they’re so different, and I spend an equal amount of time in each. Gramophone has the best selection of dance and electronic music in Chicago, and emphasis is given to local DJs. The staff couldn’t be nicer and will help you navigate the immense number of bins. They'll also offer to order something for you if it's not in the store. Dusty Groove has a fantastic collection of international artists and jazz, especially Brazilian. It's more organized and modern than Gramophone, but don't let that fool you into thinking they only carry new releases from current artists. (For more, see our complete Chicago Vinyl Tour.)
Wine Shop: Perman Wine
My biggest complaint about living in the Loop -- and I’ve got several -- is the lack of a good local wine shop. The ones near me were either insanely overpriced or specialized in cheap swill. A recommendation brought me to Perman, and I never minded doing the 20 min walk to West Loop to check out their selection. Lots of great European bottles under $15, and they have a pretty esoteric selection of liquor. It’s the only place in Chicago where I could find calvados, which they special ordered for me.
Favorite Bike Rides: The Lake Shore Drive bike path. Start around Navy Pier downtown, and then head south to Hyde Park (brunch at Valois on 53rd Street highly recommended) or go north to Lincoln Park and take a break to enjoy the Lincoln Park Conservatory and pancakes at Wheat's End.