Narrowing down where to eat on a recent trip to Chicago wasn’t easy. Did we want to revisit old favorites such as Blackbird, Naha or The Publican? Dine at high-end legend Alinea or their brand new, much praised, more casual Roister. Did we spend hours trolling the Internet, grilling the hotel concierge and asking local friends –yes, yes and yes. Can we save you time with our go to list—again-yes, yes and yes. Happy eating!
Side Note: Chicago is a city of neighborhoods and you could very easily dine well without leaving a zip code. Taxi’s and Ubers are plentiful, and you can also hop on the “L,” Chicago’s elevated train line.
Wicker Park: Right in the heart of hip Wicker Park, are our new favorite next door neighbors --Dove’s Luncheonette, and Big Star Tacos.
Dove’s is perfect for a solo meal or a cozy couples date, with counter service (just 41 stool seats) Dove’s doesn’t work for a group. A Tex-Mex diner with retro throwback chic, our lunch of chicken fried chicken with chorizo gravy with sweet peas, (a signature dish) was worth the Uber. With over 70 agaves and tequilas to choose from, we’d love to return for a casual dinner date.
It’s always a party at next-door’s Big Star, especially on a warm day or evening when the patio is packed with groups enjoying tacos and pitchers of margaritas, beers or bourbon.
After lunch, we spied someone walking by with a soft serve that looked so good we just had to ask. Right across the street at noodle heaven, Urban Belly, you must get (you don’t need to be hungry) a soft serve vanilla ice cream topped with peanut butter and jelly. Trust us.
West Loop: You could easily eat all your meals in the red hot west loop ‘triangle’ with everything on or branching off Randolph Street, a mini restaurant row.
Many visitors make Au Cheval a priority destination; fans claim this is the best burger in the country. With a no reservations policy and long waits, go early so you can grab a seat at the bar and see for yourself. (Tip: in Bucktown, sibling, Small Cheval you can get the same burger, smaller yes but with the same taste, an outdoor patio and usually no wait)
The reigning star of the West Loop, Stephanie Izard’s Girl and the Goat has not lost any steam since it opened some eight years or so ago --still an impossible reservation to come by. No luck getting a table, go and sit at the bar, and sample from the eclectic menu. The Goat empire continues across the street at Little Goat, good for breakfast and lunch—a diner with a chef’s creative twist. We loved the inventive Chinese fare at Duck, Duck, Goat washed down with killer cocktails.
The space at Avec is cool and minimal, the service is professional and friendly and the food is delicious, with many vegetarian options. Do not miss the chorizo-stuffed bacon-wrapped dates. There’s a reason you see it at every table.
We wanted to love Bad Hunter, it’s a big, lively space with an interesting veggie-centric menu, but the food was good, not great. Press has been very enthusiastic, so perhaps we hit an off night.
The Loop: After a mandatory stop at Cloud Gate in Millennium Park, or a visit to The Art Institute, go high at The Chicago Athletic Association. Reborn as a hotel, the 1920’s Venetian Gothic building, an architectural gem offers tours in conjunction with the Chicago Architecture Foundation.
Cindy’s, the rooftop restaurant at the Athletic Association has stunning panoramic views overlooking Millennium Park and Lake Michigan. The seasonal American plates compliment the view, quieter at lunch; things heat up at 5 when everyone arrives for cocktails around the fire pit or in the glass and steel atrium.
River North: Rick Bayless may be the most famous chef for Mexican fare this side of the border and his three restaurants in River North are favorite Chicago destinations.
Head to Frontera Grill, the original restaurant for casual, regional specialties while Topolobampo features more daring, sophisticated tasting menus. Xoco, right next door, is counter service only, perfect for a quick meal of Mexican street food, known for excellent tortas. (Bayless’ new Lena Brava in the West Loop has the critics going crazy—with no stoves and no gas everything is cooked open-hearth on a wood-burning stove.)
Lula Café put Logan Square on the map serving locally sourced fare on its inventive menu, you’ll find long lines at brunch and dinnertime, but we enjoyed a quiet weekday breakfast with no wait and no crowds
We had our best meal of the trip at tiny Giant. The narrow space is perennially packed thanks to fried uni shooters, homemade biscuits with jalapeno butter, crab salad with waffle fries, drool-worthy pasta and pecan-smoked baby back ribs. Come hungry and order as many small plates as your tablemates will allow. (If you wind up waiting as we did--our table was lingering and who can blame them--head to corner lounge Scofflaw for an artisan cocktail)
Fat Rice can be credited for bringing Macau cuisine into the spotlight. (a fusion of Chinese-Portuguese influences) Though everything on the menu sounds great, the namesake dish of Arroz Gordo (fat rice) is the draw, resembling paella on steroids.