Chicago: The Best of Food and Culture

Millennium Park

Millennium Park is a worth a visit year-round, whether it's for free weekly concerts and films every summer at the Frank Gehry-designed Pritzker Pavilion or ice skating in winter. Snap an obligatory selfie in front of Anish Kapoor's "Cloud Gate" stainless steel mirrored art sculpture, nicknamed "the Bean" before wandering through the blooms in Lurie Garden. This is a great spot for a picnic and kids will love splashing around in Crown Fountain, a reflecting pool bookended by two interactive video sculptures.

Chicago Architecture Foundation River Cruise

Both out-of-towners and locals rave about the Chicago Architecture Foundation River Cruise. The 90-minute tour covers more than 50 buildings along the Chicago River, including landmarks like the Wrigley Building and Tribune Tower. Each CAF-certified volunteer docent tells the stories of Chicago's history through its buildings with a slightly different perspective, so the tour never gets old, with new anecdotes and layers unveiled each time. Boats can get crowded at peak times on weekends but the great guides keep everyone entertained. Tours are offered year-round but bundle up to brave the cold come winter. Summer and autumn are the most comfortable times of year to cruise. For a more romantic option with cocktails, book the twilight river cruise.

Willis Tower Skydeck

Zoom up to the 103rd floor of the Willis Tower (née the Sears Tower) for panoramic city views at Skydeck Chicago. On a clear day you can see as far as Michigan, Wisconsin, and Indiana. If you aren't scared of heights, step out onto The Ledge, a small glass-bottomed box extending from the Skydeck and look straight down to the city 1,353 feet below. Prior to checking out The Ledge, make sure to stop by lower level museum, delivering an interactive experience that celebrates the unique personality, history, neighborhoods and sites of Chicago. Afterwards, grab a bite to eat at Kindling for meat and veggies cooked over an open fire.

The Second City

Chicago's beloved comedy club – where Tina Fey, Amy Poehler, and Dan Aykroyd got their starts – has been an institution for live comedy since 1959. After the show, enjoy beer, bites and bar games upstairs at Utopian Tailgate, a playful rooftop party-scape with super-sized Jenga, Plinko and Putterball.

Pilot Project Brewing

Chicago is known for its strong craft beer scene, with more than 150 breweries big and small throughout the metropolitan area. Try a few of the city's most interesting and newest brews at Pilot Project Brewing in Logan Square, a brewery incubator and tasting room with an ever rotating selection of limited edition beers on tap to sample. Founder Dan Abel aims to lower the barrier to entry for commercial brewing, creating a collaborative space for craft brewers to thrive.

National Museum of Mexican Art

Among the bodegas and panaderias of Pilsen, the National Museum of Mexican Art is a celebration of culture and history through colorful artwork from both sides of the border. The museum's permanent collection includes more than 9,000 pieces from ancient Mesoamerica to present day, rangingfrom folk art and sculptures to textiles and ephemera. Exhibitions often travel across the country and abroad. Special events, like the Día de los Muertos masquerade ball, showcase dance, music, literature and theater too. Admission is free and all guides are bilingual. Give yourself at least an hour to meander through all four galleries and discover stories of Mexican identity from a wide cast of characters.

Chicago Sports Museum

The interactive Chicago Sports Museum, nestled right on the Mag Mile, celebrates Chicago sporting legends while giving you a chance to play too, with simulated experiences like shooting hoops with Scottie Pippen.

Maria Pinto's Flagship Boutique

Maria Pinto is Chicago's preeminent contemporary fashion designer, dressing Michelle Obama and Oprah Winfrey over the years in custom couture. Her new flagship store in the Gold Coast celebrates the 10th anniversary of her ready-to-wear line, with versatile, timeless pieces that are easy to wear, care for and travel with. Everything is wrinkle-resistant and machine washable, so as a frequent traveler I'm sold! The stylists here are super sweet and fun too – they'll hand you a glass of wine as you shop and you're sure to walk away with an outfit that makes you feel comfortable and confident.

Breakfast

Daisies - The pastry case at this all-day cafe and bakery has new sweet and savory treats every day by pastry chef Leigh Omilinsky, accompanied by excellent coffee and tea. Seasonal produce from Frillman Farms (run by chef/owner Joe Frillman's brother) finds its way into pillowy ravioli, colorful salads, Omilinsky's pastries, ice cream and even cocktails. Come back again at dinner to try it all.

Publican Quality Bread - 2019 "Outstanding Baker" James Beard Award winner Greg Wade sells his bread wholesale to many of the best restaurants in the city, and now he has a grab-and-go cafe and retail counter in West Town too. Incredible pastries, sandwiches, baguettes and sourdough loaves – everything is made with stone milled heritage grains from small family-owned farms in the Midwest. There are always new seasonal specials to look forward to – like a cornmeal danish with pumpkin cheesecake filling for autumn.

Lunch

Kindling - Chicago's favorite new power lunch is located at one of the city's most iconic landmarks. Kindling, a 500-seat restaurant with the largest wood-fire grills in the city, is the crown jewel of Willis Tower's massive redevelopment, with a menu that appeals to families and sophisticated foodies alike, including well-marbled steaks prepared over open flame, mac and cheese gratin, three variations of wood-fired oysters and the best rotisserie chicken in the city.

Roots Handmade Pizza - If you need to try deep dish, go to Pequod's, but I personally prefer the subtly sweet malted crust on Quad Cities style pizza at Roots. You can customize your own pizza from scratch, selecting from more than 50 different toppings and Roots even makes their mozzarella from scratch every day. Of course, the mozzarella sticks are killer too. There are excellent vegan pizzas too and generously portioned salads that are healthy and hearty. This is the perfect lunch or dinner pick if you have any picky eaters in the group.

Dinner

Esmé - This is the most exciting tasting menu in Chicago right now. Chef Jenner Tomaska made a name for himself at Next and now he's running his own restaurant with his wife and partner Katrina Bravo. The menu changes completely every few months, but you can expect artful plating, creative storytelling and impeccable cooking for what's sure to be a memorable meal. The current Emmy Star Brown menu runs through December and it's super playful, whimsical and interactive, full of surprises and delights.

The Omakase Room - Chicago has seen an explosion of omakase sushi restaurants open recently, but this 10-seat, 18-course omakase experience hidden upstairs above Sushi-San is among the best. Enjoy a sake toast with master sushi chef Kaze Chan before dinner begins. Hamachi belly with banana peppers, akami nigiri with shiitake butter and chutoro tataki with black truffle vinaigrette are just a few signature bites and Chan's imaginative flavor combinations never obscure the pristine flavor of his fish – flown in from Tokyo's Toyosu Market of course.

Indienne - Chef Sujan Sarkar brings a progressive approach to Indian fine dining with his newest venture, rooted in his decades of modern European training enmeshed with the ancient, bold flavors found throughout the Indian subcontinent. There are omnivorous, vegetarian and vegan tasting menus, with highlights like passion fruit avocado pan puri. Sarkar's food is like nothing else you'll find in the city and every bite, from egg curry with lobster and uni, to jaggery coconut milk cake for dessert, will surprise and delight. Imaginative cocktails (including tableside gin tonics) and an opulent tea service equally impress.

Ummo - Best new Italian restaurant in Chicago, with sexy design, plush booths and an upstairs loft where you can party until 3 am on weekends with a DJ, vinyl records and billiards table. Chef Jose Sosa grew up in Michoacán, Mexico, spending time on his grandparents' farm and developed a passion for Italian food throughout his culinary career. Try the octopus carpaccio, the asparagus rotolo lasagna and any of the steaks, which are accompanied by whole heads of sweet roasted garlic. Desserts by pastry chef Jesús Escalera are excellent too, like a trompe-l'œil tomato with basil sorbet and a velvety twist on traditional tiramisu.