Weekends In The Windy City

“Chicago! Chicago! That toddlin’ town 

Chicago! Chicago! I’ll show you around.” 

I can’t get that song out of my head. And I can’t get the city out of my mind. I’ve been fortunate to go there on business — luckily in the spring. But frequent, short, inexpensive flights, make it a great weekend getaway for anyone living in the New York area. 

I remember being in a hotel ballroom, looking out the window, and being amazed to see Lake Michigan and the beach a couple of blocks away. When you think of a city on a beach you think of Miami or Honolulu. But it’s right there in Chicago. And residents are out there biking and jogging. 

One of the absolute best things to do in this city of architectural wonders is to get out there on the water on one of the architecture cruises which proceed from the Chicago River out onto Lake Michigan. Visit the new riverfront Chicago Architecture Center for full info, tours, and exhibits. It’s fair to say the modern skyscraper was born here as Chicago School architects explored the use of steel and glass in the early 19th century. But it was Ludwig Mies van der Rohe, who headed the architecture department of the Illinois Institute of Technology from 1939 to 1958, who is considered the most influential. It’s absolutely thrilling to sail by one after another of these famous buildings. And no matter how many times you do it, I dare you to remember all of them. 

Back on land, walk down the Magnificent Mile on Michigan Avenue which is especially beautiful when it’s in bloom with tulips in spring. All the major stores are here and somehow they’re less crowded and the clerks are nicer than in New York. It’s great for shopping here. More unusual boutiques are found in the various neighborhoods. 

A wealth of major tourist attractions is clustered in Grant Park. The Art Institute of Chicago is renowned for the largest collection of Impressionists outside of the Louvre and the radiant blue Chagall America Windows commemorating the American Bicentennial. The Shedd Aquarium, Adler Planetarium and Field Museum of Natural History are nearby. And there’s Millennium Park, now the most visited site in the Midwest. The millions (nearly 13 million tourists in the second half of 2016 alone) are largely attracted by the reflective Cloud Gate sculpture, popularly known as “The Bean.” The tourism generated by this park is believed to be responsible for adding as many as 20,000 hospitality jobs in the downtown area. The park has also surpassed Navy Pier, known for its giant Ferris Wheel, in popularity even though its visitors still number in the millions. Overall Chicago welcomed 57.7 million visitors in 2018. 

Farther from the downtown Loop, the Museum of Science and Industry is also a must-see; especially for the kids. And don’t miss the Museum of Contemporary Art (MOCA) where a major retrospective “Virgil Abloh: Figures of Speech” is on view through September 22. Hometown designer Abloh, the first African American to head a global luxury brand as artistic director of menswear for Louis Vuitton, has achieved international fame at the early age of 38. 

Chicago is also a major attraction for sports fans as it is home to two major league teams, the Chicago Cubs and the Chicago White Sox. A game is as good an excuse as any to visit the city. Tours of Cubs’ home Wrigley Field are also open to the public. 

All this sightseeing is bound to make anyone hungry. Chicago is a great eating town from its famous hot dogs to a bevy of Michelin starred spots. (Chicago has 22 Michelin starred restaurants, third only to New York and San Francisco.) Three star Alinea is the most famous. But there are so many other delicious possibilities there aren’t enough meal parts in the day. At Ryan McCaskey’s acclaimed two-star Acadia, it’s even possible to walk in for a burger at the bar if you’re not prepared for a full tasting menu. I have some favorites that have been there for years like Avec, Martial Noguier’s Bistronomic, John Manion’s La Sirena Clandestina, and Tony Priolo’s Piccolo Sogno. Love the cacio e pepe at Nico Osteria with its crunchy Parmesan bits on top. And some terrific newcomers like Pacific Standard Time, Cira, Vietnamese Hai Sous, and Proxi. 

Upmarket Mexican is having a moment and so is Mezcal. Rick Bayless has been king of the Mexican hill for years but Diana Davila at Mi Tocaya Antojeria is starting to get a lot of attention. Mezcal expert Jay Schroeder, author of Understanding Mezcal, runs a mezcaleria called Todos Santos; at Lena Brava, Rick Bayless offers 165 selections of the smoky cousin to Tequila. Not surprising that Chicago would be at the head of the pack with the new niche spirit. It’s known as a great drinking town. Craft cocktail leader The Violet Hour has been widely imitated. 

Eating isn’t the only entertainment in town. There’s plenty of music and theater. But if there’s only time for one thing, go have some laughs at the legendary Second City. Improv was never so good and there’s a reason this was a feeder school for Saturday Night Live. Alums have included John Belushi, Tina Fey, Gilda Radner, Bill Murray. If you want to explore the deep connections visit SNL: The Experience at Chicago’s Museum of Broadcast Communications. 

Where to stay? All the major brands have hotels here so you could pick by location. Maybe you want to be in walking distance of the Magnificent Mile. Of course, there’s a Four Seasons, Park Hyatt, Peninsula, Thompson. Now there’s the new St. Jane in the landmark Carbide and Carbon building which was completed in 1929 by the Burnham Brothers sons of the famous Chicago architect Daniel Burnham. Maybe you like the idea of sleeping in a building designed by Mies van der Rohe and would love the Langham. Maybe you want to check out the newest, hippest Hoxton in the artistic Fulton Market District. 

Chicago has something for everybody.

Beverly Stephen is a freelance travel, food, and lifestyle writer and co-owner of the culinary travel company Flavor Forays.