For frequent visitors, first-time explorers, or locals, the Windy City always has something fresh to see at classic sights and new favorites.
CHICAGO – Constantly reinventing itself, the city along Lake Michigan has everything: cultural treasures, dazzling architecture, and a sizzling food scene. While the Chicago icons are musts, going beyond the well-trod Magnificent Mile to neighborhoods — there are 77 — and places that feel particularly timely will clue you into the vibe of the third-largest city in the United States.
I lived and worked in Chicago for five years and cherish every return trip. Last fall (a beautiful time to go), I revisited old favorites and made new discoveries while staying at the Chicago Hilton, a massive, 1927 hotel overlooking Grant Park and Lake Michigan. A top ten list is, by definition, limited (which is the only reason seeing a ballgame at Wrigley Field isn't on the list), but these are the spots that more than make the cut.
Covid-19 travel notes: In late June, Chicago entered Phase Four of its reopening. Museums, zoos, and performance venues started to welcome people, and restaurants to offer outdoor and some indoor dining. But not everything is open yet, so if you visit this summer, check venues for hours and Covid-19 visiting protocols. The city's tourism site Choose Chicago also has helpful information. Above all, stay safe! And make sure you're current with self-quarantine requirements for visitors.
The House: Frank Lloyd Wright's Robie House
Considered by Wright to be his most fully realized Prairie Style house, this 1910 structure joined seven other Wright buildings on the UNESCO World Heritage List in 2019. It reopened last year after a brilliant restoration of elements like its earthy wall colors and Wright-designed lighting fixtures. I loved the Modern House guided tour, which stressed the radical design seen in the cantilevered eaves and the open-plan living room. The progressive South Side neighborhood of Hyde Park, home of the University of Chicago's Gothic-style campus and future home of the Obama Presidential Library, is a Metra ride from the Loop. Suburban Oak Park has other Wright sites, including Unity Temple and the Frank Lloyd Wright Home and Studio.
The Street Art: Pilsen
The bustling, largely Mexican-American neighborhood (it was originally Eastern European) on the Lower West Side is known for colorful street murals and, increasingly, restaurants and trendy galleries, many on Halsted Street. A weekend visit with a guide is the best way to appreciate the murals that started as local expression and now include works by international street artists. With a guide from Chicago's free Greeter program (the CAC also has a tour), I saw artworks on buildings and part of the two miles of murals along the 16th Street railroad embankment. Walking along 18th Street, a main commercial strip, I ended up at the superb National Museum of Mexican Art, where galleries explore the meaning of Mexican identity.
The View: Skydeck Chicago and 360 Chicago Observation Deck
The glamorous sweep of the skyline and Lake Michigan deserve a look from up high, and Chicago offers two: the 103rd-floor Skydeck at Willis Tower in the Loop, and the 94th-floor 360 Chicago at 875 North Michigan Avenue, on the Magnificent Mile. A money-saving (and line-cutting) Chicago CityPASS covered entry to both, so I compared the two.
Both have fun city exhibits and souvenirs. Skydeck has the Ledge, where small groups step out on an enclosed glass ledge for that perfect Instagram; 360 Chicago has Tilt, where an extra fee gives a small group the chance to tilt out over the city in a glass enclosure. And 360 Chicago has a bar (so does the building's 96th-floor Signature Lounge), so nice at sunset. For me, a key difference is the view. The taller Skydeck seems to put you in the center of the city, with spectacular panoramas. The lower 360 Chicago is closer to Lake Michigan, so if swoon-worthy water views matter — I felt I was almost in the lake — this might appeal more.
The Laughs: Second City
In these hyper-partisan times, Second City seems more relevant than ever. The storied comedy powerhouse — the world's largest school of improv and sketch comedy (whose alums include Tina Fey, Jordan Peele, and Jane Lynch) turned 60 in 2019 — is the perfect place to laugh at our common culture, and ourselves, in a way that feels liberating. The Old Town location offers multiple stages and shows nightly; student shows are very affordable. I saw “Grinning from Fear to Fear,” with sketches on topics from Adam and Eve to the anti-anxiety med Lexapro. Food and drink keep everyone going for third-act improv sets, when audience ideas help shape new sketches. While the theater is closed because of Covid, you can avail yourself of virtual improv shows and classes.
The Grand Museum: Art Institute of Chicago
Other mega-museums, like Field Museum or Shedd Aquarium, also reflect Chicago's energy and ambition, but I picked the Art Institute because I love the art and the location by Millennium Park. To avoid museum fatigue, I focused on the Modern Wing (in architect Renzo Piano's light-filled, soaring spaces from a 2009 addition) and the world-renowned galleries of Impressionist and Post-impressionist works. Seurat's mesmerizing A Sunday on La Grande Jatte and Caillebotte's less-known Paris Street; Rainy Day are worth the visit alone. The Modern Wing's Balcony Café is a serene spot to recharge with a snack or drink.
The Park: Millennium Park
There's a lot to love at this former railroad site, now providing more than 20 acres of green space and entertainment off Michigan Avenue in the busy Loop. Anish Kapoor's iconic steel sculpture Cloud Gate (aka “The Bean”) reflects the shapely skyline and the people exploring around it, while Jaume Plensa's Crown Fountain is a video sculpture featuring images of Chicagoans. Frank Gehry's curvaceous, gleaming Pritzker Pavilion hosts concerts and events, and gardens provide relaxing retreats. The winding BP Pedestrian Bridge connects the park to adjacent Maggie Daly Park, full of family-friendly spaces and a wintertime ice-skating ribbon.
The Smaller Museums: American Writers Museum and Driehaus Museum
Chicago's smaller museums are gems that tell big stories in wonderful ways. Downtown's new (2017), densely packed American Writers Museum has screens and panel displays that examine the contributions of poets, playwrights, journalists, and novelists from colonial days to today. A Nation of Writers has displays on 100 diverse creators, and the Visionaries and Troublemakers gallery of Chicago writers makes a perfect reading list.
The city boomed during the late 19th centurys Gilded Age, and Driehaus Museum preserves the spirit of the age in the lavish Nickerson Mansion near the Mag Mile's high-rises. With its marble staircase, dome, and carved woodwork, this rare survivor is a time capsule that interprets the era through some of the house's original furniture and exhibits of decorative objects.
The Architecture: Chicago Architecture Center River Cruise and Walking Tours
Chicago Architecture Center's new (2018) home on Wacker Drive makes an ideal starting point for appreciating the city's world-famous architectural and design legacy. Exhibits include displays on the evolution of five neighborhoods, and the interactive, 4,200-building Chicago Model deserves a look. Always high on my list are CAC's lively tours. The signature, 90-minute narrated CAFC River Cruise provides great views and stories of about 50 buildings, from Art Deco beauties to Jeanne Gang's Aqua tower. (Other companies offer cruises, but this one is excellent for architecture.) Their 85 walking — or bike or L or bus — tours include options like Walking the 606 (a railroad viaduct turned multi-neighborhood elevated trail) and Historic Treasures of Chicago's Golden Age. On the latter, I nipped into elegant buildings on Michigan and State; our guide also pointed out the Chicago Athletic Association hotel's great rooftop bar, Cindy's.
The Sound: Buddy Guy's Legends
Famously linked to Chicago, blues music was brought from the South by African-Americans and evolved to a more urban sound here. Today there's ample competition from other musical styles, but the South Loop club, run by legendary guitarist and eight-time Grammy winner Buddy Guy, helps keep the blues alive. The comfortable space has good sight lines, as well as photos of musicians and guitars from admirers like Keith Richards and Tom Petty filling the walls. They serve Cajun and Creole food, but, most of all, deliver great sounds. Buddy Guy performs in January but might show up if he's around. (I got lucky the night I was there.) Another blues stalwart, Kingston Mines, holds forth on the North Side.
The Stroll: Lakefront Trail
With beaches and park-lined stretches, the lakefront offers heart-lifting views of the skyline. The 18-mile Lakefront Trail, running from 5800 North Sheridan to 71st Street on the South Side, became so popular that in 2018 it separated into a bike trail and a pedestrian trail. Bike rentals, available around the city from Divvy stations or at places like Bike and Roll, make starting easy. One option, a ride south from Navy Pier, gives downtown skyline panoramas and access to sights like the Museum Campus. Walking around Oak Street Beach and North Avenue Beach provide the perfect combination of beach and skyscraper views.
The Food: The Food!
Chicago's food scene is as rightly famous as the skyline. This is where you should refuel.
No one does deep-dish pizza like Chicago, and Lou Malnati's — around since 1971 with more than 50 restaurants — is a fine place to try it. At the Gold Coast location, I used my knife and fork on a pie with a buttery crust, ample Wisconsin mozzarella, and California plum tomatoes. It was fresh, flavorful, and utterly filling. Salads are a good side, but I dare anyone to have room for dessert.
HaiSous Vietnamese Kitchen
Pilsen's lively restaurant scene has expanded beyond excellent Mexican fare, and this James Beard–nominated Vietnamese favorite notches things up with inventive dishes like octopus salad with roasted peanuts and coconut cream, and chicken wings in caramelized fish sauce. HaiSous's next-door café, Ca Phe Da, serves coffee, banh mis, and pho all day. Look for HaiSous among the vendors at Time Out Market, too.
Revival Food Hall
Convenient for weekday Loop sightseeing, this spot with a bar and more than fifteen local-centric vendors taps into the market hall trend in a bright space in a 1907 building. People were grabbing fried chicken at The Budlong; I had a virtuous salad at Farmer's Fridge, followed by a sublime, chocolatey cookie from HotChocolate Bakery.
The bustling, pub-like restaurant opposite Millennium Park serves thoughtful comfort food in a mellow setting with booths, banquettes, brick walls, and dark wood. A good place to unwind after sightseeing or museum-going, the cocktails are clever and the menu includes a blackened bass sandwich with chipotle aioli and a venison burger.
West Loop Choices
Extending from the Chicago River west to Ashland Avenue and taking in areas like Randolph Street's well-established restaurant row and fast-gentrifying Fulton Market, the former rough-edged meatpacking district is home to superb restaurants, Google's offices, and hip hotels like The Hoxton.
Near Union Station, diner classic Lou Mitchell's has been cracking eggs for large skillet omelets since 1923 and the days of Route 66 (Jackson Boulevard). On Randolph Street, chic Proxi, a good-value Michelin Bib Gourmand option, fills its industrial-style space with gray paneling, leather, and wood. The satisfyingly complex world street food here includes small plates like a yellowtail and pomelo salad and a grilled mushroom and yuba noodle salad. On Fulton Market, Beatrix softens its industrial space with plants and a plusher look, a cheerful setting for food from breakfast pastries to well-prepared burgers and salads. The massive Time Out Market, with 18 local favorites and a bar, is now open in Fulton Market.