The Windy City has it all: world-class museums and architecture, urban beaches and the best dining and entertainment.
A trip to the Midwest isn’t on your short list? It should be.
Whether you’re there on business, visiting the family nearby or just want to see one of America’s great cities, Chicago is well worth not flying over.
The Windy City has it all — world-class museums, stunning architecture, urban beaches, delicious cuisine and some of the best music and comedy clubs in the country. And now, finally, Cubs baseball success. Here are picks for things to do on a trip to the star of the heartland.
The Second City comedy club
What do Stephen Colbert, Tina Fey, Steve Carrell and Jane Lynch have in common? Aside from well-deserved reputations as some of the funniest entertainers in show biz, they all got their start performing improv at Second City. Take in a show to see the next generation of comedians in action.
Green Mill Cocktail Lounge
The oldest continuously run jazz club in the U.S., Green Mill features nightly performances that begin early in the evening and go into the wee hours. Music isn’t the club’s only offering — a weekly poetry slam takes place every Sunday night from 7–10 p.m. Green Mill’s décor has been kept largely intact since it opened its doors in 1907, making the lounge feel like a blast from the past.
Art & Architecture
Chicago Architecture Foundation River Cruise
The Windy City is home to some of the most beautiful, unique architecture in the country. The best, most relaxing way to take it all in is on the CAF river cruise. The 90-minute tours take passengers past more than 50 buildings while tour guides explain the history behind the architecture and the city itself. Be sure to buy your tickets in advance — the tours sell out during the summer months.
The Art Institute of Chicago & Millennium Park
The second largest art museum in America is known for its impressive collections of Impressionist and post-Impressionist art. The AIC boasts an impressive number of iconic paintings in its permanent collection, including Grant Wood’s American Gothic, Edward Hopper’s Nighthawks and more than 30 works by Monet.
The AIC is located in Millennium Park, home to the famous Cloud Gate — better known simply as “the bean.” From June through August, there are free concerts every Monday and Thursday at the Jay Pritzker Pavilion in Millennium Park.
Urban Beaches & Lakeside Activities
Oak Street Beach
Located on the shore of Lake Michigan, Oak Street Beach is the perfect place to lounge while enjoying a spectacular view of Chicago’s skyline. Be sure to visit the entrance to the Oak Street Beach underpass — it’s where you’ll find a 260-foot long mural entitled “You Know What You Should Do,” created by artist Jeff Zimmerman. The mural serves as a friendly and beautiful reminder to keep the beach clean.
The expansive Navy Pier along Lake Michigan has a little bit of everything — a botanical garden, shops, remote control boats for rent and a newly-renovated Ferris wheel. There are fireworks every Wednesday and Saturday night during the summer months and on Saturday nights throughout the fall.
Food & Drink
The Signature Lounge at the 96th
On a clear day, splurge on a drink and appetizer at The Signature Lounge on the 96th floor of the John Hancock Center. Cocktail in hand, you’ll be treated to one of the best panoramic views of the city.
Flub a Dub Chub’s Hotdog Emporium
Chicago is known for its hotdogs and this hole-in-the-wall joint has some of the best dogs in the city — all for under $10. If one of your travel buddies isn’t craving a hotdog, don’t despair — Chicago Magazine selected the Roe Burger as one of the best in the city.
Chicago Pizza and Oven Grinder Co.
Chicago’s deep dish pizza is even more famous than its hotdogs, but a lesser known (and equally delicious) specialty is the Pizza Pot Pie, found at Chicago Pizza and Oven Grinder Co. This dish has everything — Sicilian dough, homemade sauce, veggies and sausage. It’s as tasty as it sounds.