Frank Sinatra sings of Chicago being, “my kind of town.” We can’t say we blame Ol’ Blue Eyes. At its heart, Chicago, in spite of its legendary brutal winters, is an All-American city with international appeal. Rooted in history, sports, architecture and great culinary traditions—old and new—it’s a place where the high-brow and low-brow peacefully co-exist. If you're looking for a quick way to score tickets to Chicago's top destinations, CityPASS offers admission to the city's most popular attractions at a reduced rate, rolled into one ticket price. Start at a Cubs game and end at a haute cocktail lounge. Take a selfie under Cloud Gate, aka “The Bean,” ride the El, go on an architecture cruise, hobnob with a James Beard-winning chef. The endless thread of neighborhoods means that no itinerary ever has to be the same. Whether you’re here on business in the Loop, exercising retail therapy on the Mag Mile or venturing into neighborhoods such as Wicker Park, Lincoln Park or Pilsen, Chicago keeps the options in constant motion.
File this under your next Instagram photo. Take the elevators 103 floors up to experience The Ledge, a glass-enclosed structure that establishes a new litmus test for fear of heights. Don’t worry; it is indeed supported, and well worth the four states, lake and skyline views surrounding you.
It’s crazy enough to try: holding onto a bar-fitted wall of windows that tilts out 1,000 feet above Michigan Avenue. Trust us when we say those first few minutes of suspension left us feeling equal parts scary and giddy. Tip: Do look down, or what’s the whole point?
The most famous—and picturesque—boulevard in Chicago teems with year-round activity, yes, even when it’s snowing. Shoppers pour up and down the street into vertical malls, high-tech gadget stores and of course, haute couture emporiums such as the Burberry flagship, and landmarks such as Tribune Tower and 360 Chicago.
The oldest boat tour operator in the city makes a great—and lasting—first impression. Run by Chicago Architecture Foundation-certified guides, cruises unravel historical nuggets of more than 50 buildings in Chicago, and depart from Riverside Gardens, Michigan Avenue and Wacker Drive. Cruises from April to November.
TripAdvisor users named this Michigan Avenue museum the best museum in the world. We repeat: in the world. The breadth of work spans 5,000 years, with notable pieces such as George Seurat’s “A Sunday on the Grande Jatte,” Edward Hopper’s “Nighthawks” and Grant Wood’s “American Gothic.”
Millennium Park’s crown jewel, Cloud Gate, aka “The Bean,” might be the most snapped piece of architecture in Chicago. And why not? It’s just darn cool. The 110-ton elliptical structure designed by British artist Anish Kapoor is a literal mirror of the city, reflecting the clouds above and the skyline.
No game tickets? No problem. Purchase guided tours for a behind-the-ivy-wall view of the clubhouses, dugout, seating bowl, press box, bleachers and more on non-game days. Game-day itineraries subject to change. $25.
Housed in the 1893 World Fair’s Palace of Fine Arts building is the Western Hemisphere’s largest science museum. Watch baby chicks hatch, play tic-tac-toe against a robot or take a space adventure with NASA in the Omnimax Theater. With over 400,000 square feet of interactive exhibits, you'll never stop learning.
Named after Marshall Field, this natural history museum is one of the city's cultural epicenters. Travel back in time to ancient Egypt and check out some real mummies, or explore the Pawnee earth lodge to learn about Native Americans in the 1800s. And you definitely can’t miss taking a pic with Sue the T. Rex—we promise she doesn't bite!
You don’t have to get wet to experience an underwater world at the Shedd. Catch the aquatic show to watch a synchronized dolphin dance, or feel how slippery a stingray really is at the touch pool. Have you said “hi” to Luna yet? She’s the aquarium's favorite rescued sea otter. Tip: The Shedd has the best skyline view from its patio.
If Galileo was alive, he surely would approve of the planetarium’s exhibits. Experience the wonders of the night sky and learn about our solar system’s many mysteries. Just east of the main building is the Doane Observatory with the largest public aperture telescope in the Chicago area. Galaxies far, far away will never seem closer.
So we all know that Chicago is the home and birthplace of deep-dish pizza. Pizzeria Uno claims to be the first; who continued the tradition is an ongoing debate. On this we can all agree: It’s hard to resist the honking crust, layer of red sauce and cheese spread to the edge of the pan. One piece is a meal in itself.