See the Sights

There’s something undeniably exhilarating about exploring downtown Chicago.

You can stand on Oak Street beach with the sparkling waters of Lake Michigan over your right shoulder while towering skyscrapers rise over your left.

You can immerse yourself in the famous skyline by taking a stroll along the Riverwalk or hopping on an architecture boat tour along the Chicago river, which cuts through the heart of the city.

You can self-reflect (literally) at Millennium Park and grab a snap while you’re at it. The park is peppered with unique art and sculptures, including the world-famous Cloud Gate (read Bean). In the summer, you can also find popular free concerts, yoga classes and movie nights.

Lollapalooza was rebirthed in Chicago’s Grant Park years before music festivals became a full-fledged industry. Each year the festival infuses downtown with vibrant energy, community events, and world-class artists.

Eat the Eats

You’re going to need some fuel after the Magnificent Mile. Good thing Chi-town knows how to cook. Grab an Italian beef or Chicago-style hot dog with the works at Max’s or Portillo’s. Just make sure you don’t put ketchup on your dog or the locals will give you dirty looks!

Of course, your Chicago food journey won’t be complete without the seminal deep-dish pizza experience. Every Chicagoan will heatedly vouch for their favorite (*cough* Lou Malnati’s) but you really can’t go wrong with thick inches of saucy pie. 

While Chicago-style specialties may gravitate toward greasy street food, the upscale foodie will not be disappointed. Top rated spots like Alinea and Au Cheval make Chicago a hot culinary destination worldwide. Café Ba-Ba-Reeba! is a killer spot for tapas and Kuma’s Corner has the best burger in town.

Explore the Town

Beyond the typical downtown tourist spots, there are tons of funky neighborhoods to explore.

Hipster-watch at Myopic Books in Wicker Park, sip boba tea in Chinatown and party hard at Roscoe’s in Boystown.

Wrigleyville is home to the famous Cubs’ Wrigley field while Lincoln Park has a free zoo for the grown-up kids in all of us. With so many places to check out, it’s a good thing the “L” trains make it easy to get around.

Grab a Seat

The best way to cap your night in the Windy City is with a show! The theater community in Chicago is robust, and famous companies like the Goodman and Steppenwolf are great bets for finding high-quality dramas.

But perhaps Chicago is best renowned for its comedy. In fact, the city is such a comedy powerhouse that your favorite comedian probably got their start there; Fey, Colbert, Poehler, Farley, Murray, both Belushis- the list goes on and on! And the scene is still teeming with talent, with plenty of young performers vying to follow in those footsteps.

The Second City is perhaps the most well-known spot for sketch and improvisational comedy, with other comedy giants like Io (Improv Olympic) and The Annoyance not far behind on the list.

Welcome to Sweet Home Chicago! Once you visit you’ll see why so many have fallen in love with this city.

If you’re visiting Chicago, grab tickets to a comedy show or concert. EvilTickets has pre-sale, post-sale, and hotels deals to complete your weekend.