Explore the Windy City’s award-winning hotels, restaurants, and attractions
I fancy myself a Chicago know-it-all (lifelong Chicagoan, radio host, journalist, nosy neighbor), but just about every Chicagoan feels the same.
This guide highlights the USA TODAY 10Best Readers’ Choice Award winners of Chicago, from awesome restaurants and bars to the greatest hotels, events, and activities in this world-class town.
Chicago has been voted among the top 10 for Best Beer City, Most Walkable City in the U.S., and Best Summer Destination, among others — all for good reason!
Bookmark this list for your next trip to Chi-town.
Best hotels in Chicago
Voted one of the Best New Hotels in the U.S., The St. Regis Chicago is one of the city’s many architectural marvels, designed by award-winning architect Jeanne Gang. The property includes premier butler service, nightly champagne sabrage, and The St. Regis Spa, one of Chicago’s wellness meccas.
The hotel is home to two of Chicago’s finest restaurants: Tre Dita, a love letter to Tuscan cuisine, and the airy and light-filled Miru.
Insider tip: The hotel’s rooftop terrace overlooks the city with bird’s-eye views of fireworks at Navy Pier (crowned the Best Place to See Fireworks.)
Readers agree that The Peninsula Chicago Hotel is an extraordinary place to roost. Z Bar, Pierrot Gourmet, and Shanghai Terrace beckon with warm weather terraces and stellar food and beverage. Afternoon tea service in The Lobby is especially festive during the holidays when the hotel does it up with live music, extravagant decor, ice skating, and spectacular overnight packages. Those are just a few reasons readers voted this establishment among the best hotels for the holidays.
Need relief from the buzz of the city? Book a seasonal treatment at Leaf Spa at Fairmont Chicago Millennium Park, voted one of the best hotel spas in the country.
Environmentally minded visitors go for the LEED Gold-certified Virgin Hotels Chicago, voted one of the country’s best eco-friendly hotels.
The Publishing House, which has earned a 10 best ranking for Best Bed and Breakfast, will completely change the minds of travelers who don’t think they like bed and breakfasts, thanks to the chic decor, laid-back ambience, and outstanding breakfast near Chicago’s Restaurant Row.
Readers voted SOPHY Hyde Park as a Best Boutique Hotel. The South Side vibe combined with the hotel’s smart rooms, artistic indoor, and outdoor spaces complements the cultural essence of the neighborhood that the Obamas once called home.
Best Chicago restaurants, cafes, and sweet shops
When that midafternoon snooze hits, sip a phenomenal cup of joe at Big Shoulders Coffee, a Best Independent Coffee Shop winner. With a former chef-turned-coffee roaster at the helm, stop here for no-nonsense artisan beans, roasted to perfection.
There are handmade candies galore at Windy City Sweets, a 2023 winner for Best Candy Store, from nostalgic treats to signature, homemade fudge, s’mores, and more. At Katherine Anne Confections, which got a nod for Best Chocolate Shop, you’ll find seasonal flavors plus classics like salted caramel.
Stock up on bakery goods or enjoy biscuits and gravy and two-fisted sandwiches at Wheat’s End Cafe, one of the best gluten-free bakeries in the country.
In a city that takes its pizza seriously, both Chicago’s Pizza and Robert’s Pizza and Dough Co. made the top 10 for best gluten-free pizzerias for their in-house crusts and array of toppings.
The Oakville Grill & Cellar, one of 2024’s best new restaurants, has a great happy hour and weekend brunch. Featuring ingredients from farms and ranches across the Midwest, enjoy menus for lunch and dinner on the all-season patio.
Chicago has a plethora of notable steakhouses, and Asador Bastien, a Basque-inspired chophouse in River North’s Gallery District, is something really special. Another Best New Restaurant winner, here you’ll enjoy several varieties of flame-kissed beef, seafood, and a tortilla Española that will whisk you right to San Sebastian, Spain.
Traveling to or from Chicago? Don’t overlook the restaurants at O’Hare Internationl Airport, one of the best airports for dining. Notable stops include Rick Bayless’ Tortas Frontera, Berghoff Cafe for German items, cheeseburgers at Billy Goat’s, or Gold Coast Dogs for Chicago-style hot dogs and Italian beef sandwiches. For drinks, hangout at Goose Island Beer Company or Publican Tavern.
Best Chicago bars
With more than 160 Chicago breweries capturing the imagination and outsider appeal of craft beer culture, this Best Beer City continues to bag a barrel-full of awards.
Pilot Project Brewing, a springboard for startup breweries bringing exciting new brews from around the world, and Sleeping Village are both award-winning beer bars. Visit the Pilot Project Brewing’s incubator and taproom to sample beer, craft non-alcoholic brews, tea, and coffee.
Among 2024’s best new breweries, Black-owned Funkytown Brewery brings diversity to the craft brew space, winning multiple awards for suds like Hip-Hops, R&Brew, and Cuffin’ Season. Also voted a Best New Brewery by USA TODAY 10Best readers: Turner Haus, a Black, family-owned enterprise in Bronzeville. They brew and name beers after the family matriarchs.
Readers voted Chicago’s first botanical brewery and restaurant, Forbidden Root, as a Best Brewpub for its continuously rotating menu of Midwestern food and beverage tweaked with the seasons. Another Best Brewpub: Old Irving Brewing Company.
Don’t miss women-owned ERIS Brewery and Cider House, which topped the list as Best Cidery in the country.
Best events in Chicago
Chicago teems with festivals. Windy City Smokeout, an outdoor country music and BBQ festival, was a winner of the Academy of Country Music Awards’ Festival of the Year, as well as a USA TODAY 10Best Readers’ Choice Award for Best Specialty Food Festival. Count on an impressive lineup featuring some of country music’s biggest names, along with the ultimate BBQ and craft beer from around the country.
A Chicago tradition since 1980, the Taste of Chicago thrills locals and visitors who want to experience Chicago’s expansive food scene, peppered with live music, entertainment, and family fun. The free-admission event takes place over three days in Grant Park. Chicagoans don’t mourn the end of festival season when the first leaves float off trees; they just keep partying!
The Chicago German-American Oktoberfest is a wunderbar Best Oktoberfest filled with music, dancing, and lots of wurst, pretzels, and beer.
The Magnificent Mile Lights Festival winds down Michigan Avenue and up to a top 10 spot on the Best Holiday Parade list. Stroll over to Christkindlmarket, the award-winning German-style bazaar that will fill you with holiday cheer.
Best attractions and other things to do in Chicago
Whether participant or fan, the Windy City has a roster of activities for sports fans year-round. One of two classic historic ballparks still standing in the U.S., Wrigley Field, clutched a spot as one of the best MLB stadiums. The 1914 ballpark has modern amenities, from a sensory room to electric vehicle charging stations. Don’t miss iconic Chicago snacks like Garrett Popcorn, Home Run Inn pizza, Vienna Italian beef, and Anthony Bourdain’s favorite, Hot Doug’s.
When the dogs start barking, get off of your feet and onto Chicago’s First Lady Cruises, a Best Boat Tour winner, an ideal way to see iconic architecture, or settle into a kayak to paddle the Chicago River.
This city has numerous must-visit institutions, like the internationally admired Art Institute of Chicago. This Best Art Museum is rife with Hoppers, Picassos, Van Goghs, and O’Keefes.
The most popular exhibit every year at the National Museum of Mexican Art is for the Day of the Dead. The museum dazzles with gleaming altars, whimsical sugar skull sculptures, and eye-popping art celebrating the dearly departed in colorful ways that are anything but grim. It ranks as one of the best free museums in the country.
Brush up on your science smarts and feel the physics at the massive Museum of Science & Industry, the largest science museum in the Western Hemisphere and a winner for Best Science Museum in the country.
Since Chicago was deemed one of the most walkable cities in the U.S., you can easily torch some calories at the city’s first elevated park, The 606; the 18.5-mile Lakefront Trail; walking paths at Millennium Park; or just tooling around the neighborhoods.
About Jacky Runice
Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and editor specializing in separating the riff from the raff in culture, entertainment, food, travel and pure unadulterated fun. Jacky is a member of the International Food, Wine & Travel Writers Association (IFWTWA).
In her best Chicagoese, Jacky asks, “Who has the time or money to blow on hotels, attractions, restaurants, exhibits and activities that blow?”
Read more about Jacky Runice here.
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