The third largest city in America, Chicago is a metropolis with something for everyone to enjoy. Whether you’re a history buff, a sports fan, a shopaholic, a foodie, or are just ready to experience a world-class city filled with arts, culture and entertainment, there are always tons of good reasons to hop aboard flights to Chicago for your next adventure!
Although only a decade old, Millennium Park has quickly become a must-go-to spot when visiting Chicago. You’ve likely seen countless Instagrams featuring mirror-like reflections of “The Bean”. Officially called “Cloud Gate”, the giant, stainless steel structure has become a signature landmark in the Windy City. The magnificent 25-acre space that makes up the park contains spectacular architecture and public art. There are also lots of outdoor concerts, film screenings, group workouts, art installations, and other awesome events and programs.
This history-packed strip is filled with stories of important historic events and landmarks. The real reason you’ll find most visitors here, however, is for the shopping! The shops on Michigan Avenue running from the Chicago River to Oak Street, or “The Magnificent Mile” as it is commonly referred to as, has a shopping experience suited for anyone. Whether you’re looking for quaint boutiques, high-rise shopping centers, luxury department stores, designer studios, outlet shops (or really anything else you can think of!), you’re sure to find it on this iconic eight-block stretch. Bring your wallet (and maybe an extra suitcase for the way home!)
Chicago Art Institute
Featuring more than 300,000 works spanning centuries from across the globe, the Chicago Art Institute is an obvious choice when it comes to visiting one of Chicago’s many famous museums. Located in downtown Chicago, the Institute makes a great stop when visiting nearby Millennium Park. If you work up an appetite spending hours roaming the halls of the expansive collections of beautiful Impressionist and Post-Impressionist art, not to worry. Enjoy a classy lunch at Terzo Piano on the third floor, featuring both fine-dining Italian cuisine and impressive views of Lake Michigan and the city’s skyline.
Brunch: Wildberry Pancakes and Cafe
The perfect spot to fill up before a long day of sightseeing in the city, Wildberry Pancakes and Cafe offers a delicious selection of egg entrees, skillets, waffles, crepes, french toast, and of course, pancakes! A huge menu with huge portions to match, sweet-tooths will have a hard time deciding which specialty pancake they want to indulge in. The“signature berry bliss”, Oreo s’mores, tiramisu, and cinnamon roll are crowd favorites. Be prepared to wait, especially on the weekends. The great service and reasonable prices make it well worth it.
When in Rome, do as the Romans do. When in Chicago, eat deep dish pizza (even a proud New Yorker must stop by and try Chicago’s delicacy!) There’s no better spot than to do so but Giordano’s, a locally grown chain with a drool-worthy selection of stuffed crust pizzas. Favorites include the Chicago Classic and the Bacon BBQ Chicken (the tomato sauce on the pizza is replaced with barbecue sauce!).
Perfect for large groups, the high-energy atmosphere and brightly colored interior make Carnevale a fun and lively dinner spot when visiting Chicago. The deliciously flavored Latin-inspired dishes are perfectly paired with margaritas, caipirinhas, and award-winning mojitos. For the adventurous, try the signature “cotton candy cocktail”. Prices are reasonable and the wait staff is friendly.
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Located on the rooftop of the contemporary boutique Raffaello Hotel, Drumbar has a spacious outdoor terrace with beautiful views of Lake Michigan. The unique cocktail menu boasts a selection of craft drinks, rare spirits, boutique wines, and microbrews. Whether you’re enjoying your drink in the cool comfort of the leather couches inside or admiring the view of the Hancock Center outside, this trendy, prohibition-style spot is a great place to relax at the end of your day in Chicago. After 8:00pm the dress code is no longer casual so make sure you’re dressed to impress!
Nightlife: The Second City
A renowned comedy club, The Second City, is famous for launching careers of celebrity comedians like Tina Fey, Joan Rivers, Stephen Colbert, and Steve Carell, just to name a few. Known as the first ever on-going improvisational theater troupe in the United States, The Second City is now a popular spot for both sketch shows and improv classes. If you like to laugh, (who doesn’t?!) the live shows at the famed Second City won’t disappoint.
So now that we’ve helped you put together some amazing experiences in the Windy City, all that’s left for you to do is to find cheap flights to Chicago ASAP!