401 N. Franklin St., River North
Doughnuts have been enjoying a pretty awesome resurgence, and nowhere is that more evident than this family of bakeries, where out-the-door lines are a daily occurrence. Flavors run the gamut from buttermilk to gingerbread stack, but the award winning glazed is the long-standing favorite. For diehards, it might be worth it to hop from shop, to shop, to truck as the menus and daily specials vary. The truck, for example, serves strictly old fashioneds (check twitter to find out where it’s parked). Keep in mind that all three can shut down unexpectedly if stock runs out. (The other standing location is in West Loop.)
613 N. State St., River North
Come to this deliberately cluttered mom-and-pop (located in the historic Tree Studio building) for all the benefits of antique shopping, without having to deep dive for the good stuff—here, piles of vintage hotel silver salvaged from European estate sales sit next to 1950s maps found at local flea markets. And while everything on display is good, it’s the tiny kids corner—packed with books, serving sets, and vintage toys—that’s arguably the main attraction. Fair warning: Serious collectors have to be quick on the draw as much of the offering is one-of-a-kind.
212 W. Chicago Ave., River North
Every time we find ourselves in Chicago, we head straight to Blake (it's actually one of GP's absolute favorite stores in the world). They stock everything from Rick Owens to The Row to Saint Laurent, and round it out with more mid-priced brands like L’Agence. The buyers have amazing taste; it’s hard not to fall in love with this place. Photo: Racked, Chicago
Sable Kitchen & Bar
505 N. State St., River North
COVID-19 update: Temporarily closed. Located in Hotel Palomar, Sable is the destination for a few drinks or a full meal. They serve gastropub dishes with an American twist, and a long list of wood-fired flatbreads. Their 14-page cocktail menu is garnering plenty of attention, too, for its mix of old-fashioned drinks (a long list of options for a good old Martini) and new twists (Ice & Fire, for example, is a tequila-based drink with Sriracha, cucumber, agave, and fresh lime).
464 N. Halsted St., River North
A collaboration between a chef and a wine connoisseur, Chef Tony Priolo and Ciro Longobardo opened Piccolo Sogno in 2008. The modern and rustic Italian food is all about the freshest, seasonal ingredients and Italian wines. The best seats in the house, especially in the summer, are in their quiet outdoor patio.
218 W. Kinzie St., River North
Like most establishments on Brendan Sodikoff’s roster (Au Cheval, Gilt Bar), the décor at this River North steakhouse is old time-y and darkly romantic (tufted leather booths, hard-wood floors, vintage mirrors) with a dinner offering that clearly values tradition over pomp: meatloaf, crisp wedge salad, and really really good steak frites. Wash it all down with something from the classics-minded cocktail list (regulars tend to go for the Dark & Stormy).
230 W. Kinzie St., River North
The first thing you need to know about Gilt Bar is that it’s not a bar—it’s a full-on restaurant, with a pared-down menu of small-plates that rarely eclipse the $20 mark. Here you’ll find pork meatballs, ramp risotto, and steak tartare served on toast. What’s more, there is an actual bar downstairs. It’s called Curio, and with its candlelit, subterranean vibe, and impressive classic cocktail selection, it’s arguably the best date spot in town.
Doc B’s Fresh Kitchen
55 E. Grand Ave., River North
This self-professed “fast-casual” eatery prides itself on giving guests a 100 percent customizable experience. The tech-to-table system allows for lightning-fast service (order from a digital menu board, and then take a wireless tracker to your table), though if traditional waiter service is more your speed, there’s that too. Food-wise, the focus is on healthful, fresh fare, with the menus at both locations brimming with veggie-driven dishes (for the most part, produce is sourced locally) like kale slaw and grilled artichokes, in addition to comfort staples like matzo ball soup and close to a dozen burger variations (the turkey burger is a GP favorite). There's also a location in Gold Coast.
505 N. State St., River North
Located in the hub of the art and design district, the Palomar is a modern, pet-friendly, eco-friendly, organic-oriented hotel that caters to active city visitors. The hotel organizes fun group exercise classes that include guided runs along Lake Michigan and ballet barre workouts on the hotel’s sundeck. Other novel perks are the in-room massages and yoga sessions. And, if you travel with your pets, you’ll be pleased with all the amenities that they’ll enjoy. Sable, one of the best bars around, is just down the stairs.