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1. Challenge your fear of heights.

Willis Tower is one of the tallest buildings in the Western hemisphere and home to Skydeck Chicago and The Ledge. Skydeck Chicago, an observation deck on the 103rd floor, attracts more than 1.7 million visitors a year who can enjoy views of up to 50 miles out over four states. At 1,353 feet up, The Ledge lets visitors stand in glass boxes that extend out 4.3 feet from the Skydeck — it’s definitely not for those with a fear of heights. The best time to go, is just after opening (9 a.m. March to September and 10 a.m., October to February) or after 5 p.m.

2. Shop till you drop.

Oak Street is the place to go for luxury shopping — it’s home to the boutiques of like Prada, Hermes, Jimmy Choo, Harry Winston, Christian Louboutin, Dolce & Gabbana, YSL, and many others. Its high-end atmosphere shouldn’t be too surprising, as it’s nestled into the heart of Chicago’s richest neighborhood, the Gold Coast. You’ll also find plenty of fabulous restaurants and hotels in the area. 

3. Get your inner nerd on.

The Museum Campus strives to offer something scientific for everyone. It’s home to the historic Adler Planetarium, the Shedd Aquarium, and the Field Museum of Natural History. Plus, it has spectacular views of the Chicago skyline.

4. Satisfy your sweet tooth.

For a fun activity, you can take a class at Give Me Some Sugar in Roscoe Village. There are baking and decorating classes for adults and children, and you can also book private parties. While the Friday night BYOB class, “Cupcakes & Cocktails”, trends towards a more female audience, there’s also the newest class, “Bros with Doughs,” which teaches four guy-focused baking recipes (and includes a free beer for each guest).

5. Hit the park.

Millennium Park has attractions for all travelers. First of all, it has great views of the lake and city — you can take them in via walking, cycling, skating, running, or even just sitting on a picnic blanket or bench. 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” (you probably know it as the Bean), and the Lurie Garden, which wows with year-round flower displays. There’s always something going on, from concerts to festivals to outdoor yoga classes to food truck gatherings.

6. Connect with furry friends.

The Lincoln Park Zoo is two miles north of downtown Chicago in the Lincoln Park neighborhood. The best part? There is no admission fee. If you’re there on a Wednesday or Saturday, check out the nearby Green City Market for all sorts of goodies: green smoothies, cookies, carnitas, crepes, fruits, veggies, and more.

7. Laugh out loud.

Chicago is home to the legendary Second City Comedy Club, where you can catch improv comedy at its best. Because it’s such a hot spot — it’s been thriving since 1959 — book weekend tickets well in advance. Is your show sold out? There are plenty of other comedy clubs to visit, like the iO Theater and the Laugh Factory.

8. Take a tour by land or by river.

The Chicago Architecture Foundation River Cruise by Chicago’s First Lady Cruises offers a guided tour that showcases the city’s architecture from the comforts of a riverboat. This is a great way to see a lot of the city in just 90 minutes. 

Don’t have your sea legs about you? You might enjoy the Palmer House Hilton History is Hott Tour. The historic Palmer House hotel hosted every president from Harry Truman to George W. Bush. To highlight its storied past, the property features private tours through the recently-launched historic corridor by resident “Artifacts Associates.” After the tour, guests get to take home chocolate bouchons (and the recipe), a postcard, and a small history book.

9. Listen to the Windy City blues.

Chi-town is big on the blues. Bars like 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 — it’s the largest, free blues festival in the world. 

10. Feast on food and art.

Fulton Market Kitchen is a creative hub for all things culinary and artistic, taking a page out of the playbook of New York City’s art scene in the 1980s and the Wynwood district in Miami. You can dine, drink ,and enjoy artists’ work here.

If you want more art, there’s the Art Institute of Chicago, which has a world-renowned collections. On Tuesdays and Thursdays, admission is free from 6 to 9 p.m.

11. Have a cup of tea.

Afternoon tea is serious business in Chicago, and there are many options. The aforementioned Palmer House has a lovely afternoon tea, as does the Drake. You can also try the Allis inside the SoHo House (it’s one of the public eateries within the members-only club). For a Hamilton-inspired afternoon tea, you can visit to the Lobby Lounge in the JW Marriott Chicago — it has a high tea menu featuring sweets that Hamilton loved in post-revolutionary America, along with savory elements influenced by his upbringing in the British West Indies. 

12. Hop on a bike and hit the trails.

Cycling the Lakeshore Path is an amazing way to see the beautiful skyline of Chicago. In the summer, it can get a bit crowded, but it’s totally worth braving the hoards. There’s now a large green space at the Fullerton entrance with incredible views — it’s a great spot to pop off your bike for a picnic.

13. Empty your glass.

If you’re looking to imbibe, there are plenty of options in Chicago. You can sip on whiskey at Fountainhead, which is famous for its large selection, or take a walk on the wild side at Apogee, one of the city’s hottest rooftop lounges. The talk on the street is that they take cocktails to new heights — literally, because the bar is located on the 26th floor of the Dana Hotel & Spa. The Up and Up Rooftop bar at the Robey Hotel grabs guests’ attention with its art-deco architecture — as soon as you enter, you might feel like you’ve been transported to the Roaring ’20s.

Need a place to stay? Check out our reviews and photos of 102 Chicago hotels.

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