Take in the view from the sky-high heights of the Willis Tower, the second-tallest building in the United States. From the 103rd floor, look out over 4 states and the Windy City's urban sprawl, and then test your vertigo on a glass balcony to peer down at the streets and skyscrapers of Chicago beneath your feet.

Step into an elevator and be whisked to new heights in just 60 seconds, waiting for the ear-popping sensation as you ascend to the Skydeck at the Willis Tower. Standing 1,353 feet (412 m) above the Midwest metropolis, the Willis Tower's steel-framed structure was specifically designed to withstand the city's infamous wind—you may even feel a slight sway if visiting during a blustery spell.

Be sure to schedule your appointment in advanced!

Lock Chicago is an innovative new Escape Room adventure opening up in the Chicago area. For those who aren't familiar, an Escape Room is a space that has been decorated, designed, and decked out with a theme and puzzles that you and a group of friends will have an hour to solve. Its a perfect game for any group of friends, and you can book either a private room for yourselves or join a public game.

Restored by former Hollywood set designers Robin Standefer and Stephen Alesch of Roman and Williams Buildings and Interiors, the city's coolest hotel, in an 1893 gentleman's sporting club, is more than just a place to stay. A dimly lit, wood-paneled game room is studded with pool, checkers, chess, and shuffleboard tables for booze-fueled play into the wee hours—there's even a bocce court lined with oyster shell fragments—and upstairs, the rooftop terrace at Cindy's serves the best brunch in town, with a view of Millenium Park to match.

If you want to visit Chicago's first craft-cocktail den, you'll need to follow some house rules, among them no cell phones, no baseball hats, no cosmos. But those who find the decade-old Bucktown speakeasy's secret entrance behind a colorful wall mural will be rewarded for their obedience. The interiors look like a Victorian salon by way of Paris, with opulent gray curtains against the blue backdrop, crystal chandeliers, and modernist leather wingback chairs, and the artisanal, pre-Prohibition drinks are transcendent. Coming with a group? Ladle-up the brandy- and scotch-infused Violet Hour Punch No. 6.

No trip to Chicago would be complete without a souvenir selfie taken in front of Anish Kapoor's iconic Cloud Gate statue, also known as The Bean, near the entrance to Millenium Park. But those who venture farther into Grant Park's most famous square will be rewarded with plenty of other amusements. In the summer, the hulking steel-covered bandshell at the Frank Gehry–designed Jay Pritzker Pavilion plays host to a bevy of alfresco opera and symphony performances, and headlining artists like Arcade Fire and The Killers, take the stages at the annual Lollapalooza Festival.

A leisurely boat tour is perhaps the best way to survey the city's impressive architectural legacy, which includes works by pioneering modernist designers such as Mies van der Rohe and Bertrand Goldberg. Don't have your sea legs? Walking tours led by the Chicago Architectural Foundation start at the Riverwalk, a 1.3-mile-long stretch along the Chicago River that is dotted with outdoor cafés and restaurants and offers some of the best views in the city.

Forget the deep-dish pizza and giardiniera-topped sausages—though, a case can always be made for sampling a city's fast food with gusto. If you have only one meal here, beeline to Lincoln Park for the three Michelin-starred cuisine concocted by Grant Achatz at Alinea, one of the world's best restaurants. The dining room was renovated last year with Parisian inspired influences (think velvety banquettes and ornate architectural molding) that make it almost as pretty as the avant-garde dishes that arrive at your table—lamb loin with blackberries and black garlic, Japanese icefish with fermented kumquat sauce. Almost.

Tina Fey, Bill Murray, Steve Carrell—they all got their start at the legendary comedy venue The Second City, so the odds of seeing a future Saturday Night Live cast member are in your favor. Go for a show or sign up for a one of their three-day improvisational intensives, which can help you unearth your inner comedian through a series of unexpected group prompts.

Chicago's answer to New York City's High Line, the 606 is an elevated park trail on a converted railway line that draws locals and visitors alike. The path connects Northside Chicago neighborhoods from Bucktown to Humbolt Park, and interactive works by local artists span its length. The best way to see it all? Rent a Divvy bike for the day, then hit the pavement. There are plenty of places to pull off along the way for a mid-day snack.

Charlie Chaplin and Frank Sinatra drank here. So did Al Capone—in fact, Scarface likely made use of a trapdoor behind the bar that led to secret underground tunnels for a quick getaway. The 1907 bar was a Prohibition-era hangout for mobsters and gamblers, but it was also the place for the best jazz in town. Billie Holiday, Tommy Dorsey, and Benny Goodman all played at the Green Mill, and the club continues to draw musical legends, making it more than worth the cab ride out of the way to Uptown.

A dinosaur named Sue—the largest, most complete T-Rex skeleton on the planet—greets visitors at the north entrance to The Field, where you can explore the 5,000-year-old rooms of a reconstructed Egyptian tomb and walk through a stunning recreation of an 1800s Native American earth lodge. The museum also houses some 30 million objects, from natural history specimens to anthropological collections, many of which were part of the exhibits on display during the 1893 World's Columbian Expo. (You can see more history from the Chicago World's Fair at the Museum of Science and Industry, 10 minutes away.)

Sports fanatics can get their fill of history of legendary Chicago sports venues while making stops for photo ops in front of The United Center, Wrigley Field, Soldier Field, and US Cellular Field. Your guided tour ends at Harry Caray's Water Tower with a visit to the Chicago Sports Museum.

See the homes of Chicago's iconic sports teams as you are escorted in a comfortable van to the city's top sports parks, learning the history of each during your journey. Begin by visiting the home of the Chicago Cubs—Wrigley Field. Originally built in 1914 as Weeghman Park for the Chicago Federal League baseball team, the Chicago Whales, the stadium name was changed when chewing-gum titan William Wrigley Jr. purchased the team in 1921.

Next, stop at the United Center, home of the Chicago Bulls basketball team and Blackhawks hockey team, to see the bronze Michael Jordan statue, officially known as The Spirit. A tourist favorite, the statue was created shortly after Jordan's retirement to commemorate his 3-consecutive NBA championships as a Chicago Bull.

Your next destination is the oldest NFL stadium, Soldier Field. This lakefront field is home to the Chicago Bears. Named in 1925, the field serves as a memorial to American soldiers who have died in wars. Take a photo in front of US Cellular Field ballpark, home of the Chicago White Sox, before heading to Harry Caray's Water Tower. Here you are given admission to the Chicago Sports Museum to continue your exploration of the city's rich sports history.

Seeing one of baseball's last manual scoreboards in action makes a trip to Wrigley Field worth it. Couldn't snag a ticket to the big game now that the Cubs are World Series champs? Wannabe statisticians and sports commentators can't leave the Windy City without a trip to Wrigleyville, the always-buzzing assemblage of bars, beer gardens, and restaurants that surround the iconic 103-year-old stadium. Make your way to divey Nisei Lounge, a 1951 stalwart where you can play darts between innings.