What is it about New York and Chicago? The rivalry runs deep, and I’m not talking about the Knicks and the Bulls back in the day. For decades these two cities have debated about which is better. But of course New Yorkers say there’s no need for discussion.
Take a trip there to settle it for yourself.
I long wanted to get to Chi-town. I had heard it was like a little New York, but clean. Curiosity was killing me. I was born in Indiana. How I never made it to Chicago all these years is a mystery. But this spring, alas, I ventured to the Windy City when I would be assured some warmth.
New Yorker that I am, I wasn’t going to roll up in there without a little bit of attitude and feeling like, “We’re No. 1.” But after taking the train from the airport to downtown and hitting Michigan Avenue, with all that amazing architecture—the classical, historic and the modern mix beautifully—the tough-girl game collapsed almost immediately.
I checked into the elegant LondonHouse Chicago. It’s in the historic London Guarantee & Accident Building, with modern touches such as a tri-level rooftop bar, spa and all glass tower. It overlooks the Chicago River. I was in the lap of luxury, like some of New York’s finest. Chicago was giving New York a run for the money for sure.
It started with the long walk on the Riverwalk and a nice lunch at City Winery, just a stone’s throw from the river. By the time I made the rounds at some of the city’s best jazz clubs, such as Andy’s and the Green Mill, it was a wrap. I was in love.
I fell hard, and you likely will too. Here’s what to do and see when you go.
Make your way to Millennium Park
Millennium Park has great views of the lake and city. Cycle, walk, skate, run, picnic or simply sit and enjoy the views and sounds. The 24.5-acre park features Frank Gehry’s Pritzker Pavilion and serpentine bridge, Jaume Plensa’s Crown Fountain, Anish Kapoor’s 110-ton Cloud Gate (“The Bean”) and the Lurie Garden, which wows with year-round flower displays and hosts monthly garden walks. There’s always something going on—concerts, festivals, yoga, food trucks. Big fun!
Laugh out loud
Chicago is home to the legendary Second City Comedy Club. Check out improv comedy at its best. There’s a good reason it’s been around since 1959. Because it’s such a hot spot, book weekend tickets in advance.
Bike the Lakeshore Path
The Lakeshore Path is an amazing way to discover the beautiful skyline of Chicago. In the summer, it can get a bit crowded, because the lakeshore is basically like an ocean front, but the ride is totally worth it. Now, with fall approaching, it’s a great time to go. There’s a large green space at the Fullerton entrance with an incredible view of the skyline.
Take a tour
The Chicago Architecture Foundation River Cruise by Chicago’s First Lady Cruises offers a guided riverboat cruise that showcases the city’s architecture. This cruise is a great way to see a lot of the city and in just 90 minutes.
Hear the Windy City blues
Much as Chicago has great jazz, it’s also big on the blues. Bars such as Kingston Mines, Rosa’s Lounge and B.L.U.E.S are go-to blues joints. The biggest blues fans might want to schedule a visit during the Chicago Blues Festival, held in June and the largest free blues festival in the world. Jazz heads can come to town during the annual four-day jazz festival that includes Labor Day weekend.
Visit the legendary
Lincoln Park Zoo
The Lincoln Park Zoo is 2 miles north of the Loop in the Lincoln Park neighborhood. The whole family can enjoy dozens of species. There is no admission fee. All of the exhibits are free and include Regenstein Small Mammal-Reptile House, Kovler Lion House and McCormick Bird House. If you’re there on a Wednesday or Saturday, check out the nearby Green City Market for green smoothies, cookies, carnitas, crepes, fruits, veggies and more.
Take in the tower
Willis Tower is one of the tallest buildings in the Western Hemisphere and home to Skydeck Chicago and The Ledge. Skydeck Chicago attracts more than 1.7 million visitors a year who enjoy views of up to 50 miles and four states. At 1,353 feet up, The Ledge’s glass boxes extend out 4.3 feet from the skyscraper’s Skydeck on the 103rd floor. The best time to go is just after opening at 9 a.m., March to September and 10 a.m., October to February or after 5 p.m.
Feast on food and art
Fulton Market Kitchen is a portal of collective creativity, integrating various art media and styles with imaginative cocktails and cuisine. In takes a page out of the playbook of New York City’s art scene in the 1980s. Eat, drink and enjoy artists’ work.
Then there’s the Art Institute of Chicago, with its exhibits and world renown collections. Children under 14 get in for free.
Sip on a cup of tea
Afternoon tea is serious business in Chicago. There are many options. Consider The Palmer House, The Drake, the Allis inside the SoHo House or the Lobby Lounge in the JW Marriott.
Make everybody happy
The Museum Campus strives to offer something for everyone. Between the Adler Planetarium, the Shedd Aquarium and the Field Museum of Natural History, they will likely accomplish that.