Three Perfect Days in Chicago—Without the Crowds

The third biggest city in the US, Chicago is a world-class metropolis where the pizza soars nearly as high as the architecture, where celebrity chefs are as vaunted as Cubs players, and where the snowy serenity of extended winter plows the way for summers spent outside at lakefront beaches, rooftop bars, and street festivals.

“Chicago holds endless awe for me, most often in small moments as I move through its 77 historic neighborhoods,” explains Maggie Hennessy, Chicago food writer and restaurant critic. “I feel this awe each time I take in the low-slung, whitewashed brick building that houses the superb River North watering hole Rossi’s Liquors—one of a few structures that shows what this river-hugging stretch of Chicago looked like back when it was all industry, rail, and newspaper production. It strikes me when I bike south on LaSalle Street and Downtown's majestic Art Deco-style Chicago Board of Trade rises into view and my breath catches in my chest. I feel it when the tiny, magnetic Bucktown bistro Le Bouchon is buzzing with restaurant industry pros on a Monday night (aka half-price wine night), and when I hop off the water taxi at the beautiful Tom Ping Park, aka the Chinatown stop.”

It’s impossible to whittle down a Chicago itinerary that captures it all, but it’s decidedly possible to get a taste of what makes this city so special and to find activities—and eats—that will delight any type of traveler. In order to distill this guide down to digestible itineraries, we’ve consulted with a few on-the-ground Chicago taste-makers, and divvied it into sections aimed at food lovers, families, and adventurous travelers—three distinct approaches that each offer a unique point of view on the Second City. This itinerary won’t include any downtown tourists draws that you might see on other lists, but it will invite you into surrounding neighborhoods to check out everything from vibrant, old-timey music lounges and inclusive boutiques, to late-night speakeasies and lush conservatories. Everyone knows about the Chicago River and the Willis Tower, but have you considered kayaking the river through a veritable canyon of architecture? Deep-dish pizza and Chicago-style hot dogs have earned their ranks among any Chicago bucket list, but don’t miss the restaurants that have pioneered the farm-to-table movement, or sliced Beijing duck tableside for generations.

Chicago may be the Second City, but this major metropolis is second-to-none when it comes to world-class entertainment for any type of worldly traveler.

See: Some improv. Chicago is the cultural epicenter of live comedy. The Second City is rightfully renowned, but for a more intimate and less touristy experience, venture further afield from Old Town to places like The iO Theater, The Lincoln Lodge, and The Annoyance Theatre.

Touch: The stingrays at the Shedd Aquarium. One of the marquee interactive experiences at the iconic aquarium, a cornerstone of Museum Campus, Stingray Touch allows guests of all ages to touch—and even feed—the ocean creatures.

Smell: The roses (and thousands of other plants and flowers) at the Garfield Park Conservatory. Described as “landscape art under glass,” the two-acre conservatory (one of the largest in the country) contains enchanting rooms like the Desert House, Palm House, and Fern Room.

Hear: Live jazz at the Green Mill Cocktail Lounge. Once frequented by Al Capone, this enduring Uptown haunt (open since 1907) feels like a perfectly preserved fossil, with its classic cocktails, classic music, and classic underground tunnels used by mobsters during Prohibition.

Taste: Your way around the West Loop. Home to chefs and brands like Stephanie Izard, Rick Bayless, Paul Kahan, Soho House, Nobu, Grant Achatz, and Curtis Duffy, the downtown neighborhood has grown past Restaurant Row to become a veritable Disneyland of destination dining.

Home to the James Beard Awards, Chicago is one of the foremost dining cities in the world. Across all dining styles, price points, neighborhoods and cuisines, good food is omnipresent in Chicago, from the taquerias of Little Village and Pilsen, to the multi-course tasting menus in the West Loop, and the timeworn Chinese and Vietnamese traditions in Uptown. “I think Chicago is a very approachable city,” says Rob Levitt, head butcher and chef at Publican Quality Meats in perpetually buzzy Fulton Market. “The Chicago restaurant community really supports each other and I feel like there is a great camaraderie amongst chefs and cooks and hospitality folks. This all translates to a diverse, approachable dining scene with everything from Michelin's brightest to world-class sausages and a genuine focus on hospitality.” Criss-crossing the city with a food focus, sampling different cuisines and styles for each meal and experience, is a great way to scratch the surface of this tasty wonderland.

10 am - Rise and shine with brunch at Lula Cafe. 
Described by Hennessy as one of her “favorite places to eat and drink and feel the invigorating joy of being alive,” recently James Beard-gilded Lula Cafe is famed for its farm-to-table efforts, and for its pancakes. Much of the menu rotates readily, which means, on any given lazy morning, your options may include Berry Almond Danishes with chamomile and goat cheese, Broccolini with crispy Duck Egg, and Sourdough French Toast with White Chocolate Shortbread Crumble. But those pancakes are eternal.

12 pm - Feast your eyes at the Chinese American Museum of Chicago. 
Unearth the stories, struggles, and successes of Chinese-American cuisine in the US at Chinatown’s intimate Chinese American Museum of Chicago. Here, a culinary exhibit traces immigrant roots in America, through traditions like chop suey and dim sum, and to iconic Chinese restaurants in Chicago, both past and present.

1:30 pm - Snag a sandwich at Publican Quality Meats.
“PQM is like a cross-section of the Chicago dining scene packed into a cute, little corner of one of its hottest neighborhoods” says Levitt owner of the butcher shop that has something for everyone, from boneless chicken breasts to dry-aged ribeye steaks, and plenty of unusual cuts for the adventurous home cook. They also have killer sandwiches, like Smoked Turkey with Russian Dressing and Cabbage Slaw, and Crispy Ham with Parsley Butter and White Cheddar.

3 pm - Grab an afternoon snack at Pretty Cool Ice Cream.
For a sweet treat, it doesn’t get much more whimsical than the quirky and crafty ice cream pops at Pretty Cool Ice Cream. With locations in Logan Square and Lincoln Park, the cute shops—from acclaimed pastry chef Dana Cree—sling singular flavors like Goat Cheese Black Raspberry Swirl, Peanut Butter Potato Chip, and Caramel Horchata Crunch.

5 pm - Enjoy Happy Hour at Nobody’s Darling.
Raise a martini glass at Nobody’s Darling, a queer- and Black-owned cocktail bar—with a penchant for non-alcoholic mocktails—in Andersonville. The neighborhood bar, which was nominated for a James Beard Award, features tipples like Lychee Martinis and Virgin Daiquiris with Maple-Ginger Syrup.

7:30 pm - Feast on Beijing duck at Sun Wah BBQ.
A bucket list-worthy Chicago dining experience, you gotta veer off-menu to order the multi-course Beijing duck experience at Uptown’s Hong Kong-style Sun Wah BBQ. The spread utilizes an entire barbecued duck, featured in soup, fried rice, and as slices of succulent poultry with glistening crispy skin.

11 pm - Find your way to Osito’s Tap for a speakeasy nightcap.
Nestled within a nondescript greystone building in Little Village, a historically Czech neighborhood that’s since become an epicenter for Latinx culture and cuisine, Osito’s Tap is an unexpected hideaway for inventive cocktails and mocktails (try the coffee-mezcal slushy) and—should you still have room for a late-night snack—Burnt Basque Cheesecake.

As evidenced by Ferris Bueller, Chicago is a great place for a day off. And even if you’re not looking to visit the Willis Tower or crash a parade, there’s still plenty of things to do for visitors of all ages. “Chicago is a world-class city, recognized globally for incredible contributions to culture, art, science, cuisine and so much more,” says Meghan Curran, chief marketing and experience officer at Shedd Aquarium. “Chicago’s museum scene truly sets us apart, boasting countless renowned institutions, both big and small, nestled throughout the city’s neighborhoods and punctuating our stunning lakefront.” For families in particular, the city is a giant playground of activities, home to enchanting parks, kid-centric restaurant menus, immersive museums, and of course, pizza for days.

9 am - Go sweet and savory with pancakes at Little Goat Diner
Since moving to its new home on the Southport Corridor, Little Goat Diner has doubled down on the edible whimsy. The handiwork of Top Chef legend Stephanie Izard, the menu takes a something-for-everyone approach to contemporary diner fare, including sweets like PB&J Pancakes (with strawberry jam, maple, and peanut butter crunch), and savories like Okonomiyaki (savory Japanese pancakes with sunny-side egg, kewpie, and bonito crunch).

12 pm - Peruse all-ages literature at Andersonville’s Women & Children First bookstore
Celebrating and amplifying underrepresented voices is the M.O. at Women & Children First, a longstanding (since 1979!) indie bookstore in Andersonville. Run by self-described trans-inclusive feminists, the sunny storefront features inspiring, empowering, and engaging literature for all age groups, including a whole section dedicated to banned books.

1:30 pm - Make a splash (figuratively speaking) at Shedd Aquarium
Perched on the shores of Lake Michigan, the Shedd Aquarium is an aquatic wonderland for all generations, home to the kinds of animals—e.g. beluga whales, otters, stingrays—that make kids giddy. Adds Curran, “Shedd Aquarium [lets kids] come face-to-face with incredible animals from large beluga whales to tiny zooplankton—all while learning how to protect our blue planet.”

4 pm - Stretch your legs—and hit the slides—at Maggie Daley Park
When it comes to family-centric parks, places like Lincoln Park and Millennium Park get a lot of the focus (for reasons involving zoos and reflective beans). But cross the windy BP Pedestrian Bridge from Millennium into Maggie Daley Park, and you’ll find a newer, 20-acre oasis where fantastical, soaring playgrounds share space with a mini golf course, climbing walls, picnic groves, and, when in season, an ice skating “ribbon.”

6 pm - Experience real-deal deep-dish at Lou Malnati’s
Round out your day with dinner at one of Chicago’s foremost deep-dish institutions: Lou Malnati’s. Originally founded in suburban Lincolnwood, and now with several locations throughout Chicagoland, the homey pizzerias are known for their casserole-like pies, layered with sausage, tomato sauce, and mozzarella within a buttery crust.

Compared to cities like Seattle or Los Angeles, Chicago may not be the most obvious destination for outdoorsy exploration and adventure—this is, after all, the middle of the Midwest, in all its flatness. But regardless, Chicago is proof that you don’t need mountains, or an ocean, to thrill. This is a city where the skyscrapers form architectural canyons (and provide adrenaline-pumping rooftop views), and where Lake Michigan, in all its sea-sized glory, stretches as far as the eye can see. “Kayaking on the Chicago River, through the canyons of glass and steel, is by far the most incredible way to see Chicago,” says Dave Olson, owner of Kayak Chicago. “Gliding through the river with a duck-eye view, while skyscrapers tower overhead, there is a peacefulness on the water, while the city's hustle and bustle is full-steam ahead on the streets above.” Awe-inspiring beauty aside, adventurists have plenty to keep them energized, from water activities and to elevated trails, to ghost tours and omakases.

9:30 am - Eat pastries al fresco at Plein Air Cafe
Enjoy breakfast under the sun on the tree-lined patio at Plein Air Cafe, a French atelier-inspired eatery located next door to Frank Lloyd Wright’s Robie House in Hyde Park. In addition to Biscuit Sandwiches and mascarpone-stuffed French Toast, you’ll find savory Spinach Pies, Meatloaf Tartines, and more.

11 am - Hit the Chicago River on a self-guided kayak tour
Kayak Chicago offers both kayak and paddle board rentals (along with guided tours) from three different locations, including a Goose Island outpost where paddlers can suit up and hit the river. Paddling south, guests can head south into the architectural canyon of downtown, under bridges and past iconic towers like the Marina Towers, the Willis Tower, and the new St. Regis Chicago.

2 pm - Stroll an elevated park
Explore Chicago’s highest park: the elevated 606 Trail, which spans 2.7 miles over Bucktown, Logan Square, and Humboldt Park, along a former rail line. “I think of it as a mini version of New York’s High Line,” explains artist and Bucktown resident, Laura Collins. “The foliage is beautiful in the summer and fall so that’s the ideal time to take a stroll and check it out, and there are some fun spots off the trail like, The Stop Along and Small Cheval. Both have outdoor seating, delicious food and are great with allergies.”

4 pm - Gangsters & Ghost Tour
Once home to notorious ne'er-do-wells like Al Capone, John Dillinger, and Baby Face Nelson, Chicago is as well-known for its gangsters as it is SNL alumni, and the best way to stroll down sordid memory lane is on a Gangsters & Ghost Tour. Guided walking tours are held in the Loop, known as the “Vice District” in the 1920s and ’30s, exploring secretive—and even haunted—hideaways, former speakeasies, and underground tunnels.

7 pm - Experience a mystery tasting menu at Omakase Yume
The omakase trend hit Chicago in a big way these past few years, with recent entries like Omakase Yume earning praise from Michelin. Courtesy of Kate Park and chef Sangtae Park, each meal at this intimate West Loop nook promises a spree of 16 mystery dishes, all based on freshness and the chef’s whim, featuring unexpected ingredients and techniques along the way (think: Kimchi Puree), and straight-up sushi artistry.

Chicago Athletic Association ($$)
This is an architectural stunner located directly across the street from Millennium Park, and up the road from the iconic Art Institute of Chicago, home to one of the most sought-after rooftop bars in town, Cindy’s Rooftop. “As an Art Institute alumni, I always recommend visiting the museum and then popping over to Cindy’s for drinks with an incredible view of Millennium Park and the lake,” adds Collins. “In winter, you can watch the ice skaters near Cloud Gate (The Bean!), and in summer you can watch people splash and play at Crown Fountain.”

The Robey ($$$)
The tallest building in Wicker Park, this twee stunner offers a unique vantage point from which to view the skyline, along with a variety of room sizes and styles, two different rooftop lounges, and convenient proximity to Chicago’s northwest side neighborhoods.

Park Hyatt Chicago ($$$$)
Magnificent Mile luxury is on full display at the Park Hyatt Chicago. Located amidst the most high-end designer stores in town, the opulent property features its own art gallery, a lavish spa, and fine dining.

How to get around
Pretty much everything in Chicago is easily accessible via the widespread CTA, the nation’s second-largest public transit network. Adds Hennessy, “If you take the time to explore Chicago as people have for centuries—on foot, on a bike, on public transit—you'll feel this magic, too, of being part of something historic and monolithic that's also forever evolving; that's busy, loud, sometimes rude and intoxicatingly alive.”

When to plan your visit
Winters in Chicago are notoriously icy and overextended, and Spring can be fickle and rainy, but summer and fall are magical in Chicago. Summer also brings street fests, baseball games, concerts, and blissful weather.

Your fun Chicago dinner party fact
The word “Chicago” translates from the Algonquin word “Shikaakwa,” which means onion, so named for the early abundance of wild alliums growing along the region’s natural lakes and streams.

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