Listen to some jazz and swing music at the Green Mill cocktail lounge, a true piece of history that first opened in 1907. Along with its connections to the Chicago mob scene, the lounge is also known for the poetry slams it hosts every Sunday night.
Watch from North Avenue Beach (or an apartment that overlooks the beach) as historic fighter planes perform daredevil maneuvers in the sky for Chicago's annual Air and Water Show. The show takes places August 15th and 16th from 10 am till 3 pm.
Catch a show at the comedy club Second City, whose most notable alumni include Steve Carell and Tina Fey.
Stroll through Grant Park, which includes landmarks such as Millennium park and Buckingham Fountain.
Dine at the Publican, which is one of Chicago's best restaurants that pays "homage to beer, pork, and oysters." There's something for everyone on the eclectic menu and the restaurant's European-style beer hall interior makes for a fun atmosphere.
Order a juicy Italian beef sandwich at Portillo's, which started off as a small hot dog stand in Chicago and grew to a restaurant chain with locations all over Chicago and its suburbs. It's most famous for its Italian beef, although the hot dog and chopped salad are also favorites.
Learn about (and taste) one of the most popular Chicago beers on the Goose Island Beer Company's brewery tour.
Cheer on the cubs at Wrigley Field or the White Sox at Citi Field. Cubs fans insist that Wrigley Field is an institution and White Sox fans claim Citi Field is better because it's newer. No matter where you end up, both make for a great afternoon or evening in the city.
Get up close and personal with beautiful butterflies at the Jody Istock butterfly haven at the Peggy Notebaert Nature Museum.
Enjoy a performance at the Tony award winning Chicago Shakespeare theater on Navy Pier. You can sit close enough to the stage that you feel like a part of the performance.
Chow down on some of the best BBQ in the city at Green Street Smoked Meats. Menu favorites include the brisket, pulled pork, and frito pie.
Look down at the city from 1,353 feet above in the Willis Tower's Skydeck, which is open 7 days a week.
Lounge on the lawn and listen to one of the many artists that perform at Chicago's Ravinia Festival which runs from mid-May till September and features genres ranging from symphony to rock to country.
Visit the Art Institute, which TripAdvisor named the number one museum in the world last year. Its exhibitions appeal to all ages.
Sip on cocktails at the J. Parker, a classy rooftop bar that sits above the Hotel Lincoln in Lincoln Park. You'll enjoy spectacular views of the city and Lake Michigan.
Browse the fresh offerings at Logan Square's farmers market, which takes place every Sunday from 10 am till 3 pm May 17th through October 25th.
Hang out with your favorite animals at the Lincoln Park Zoo, which is open to the public year round.
Wander through the stuffed book shelves of Wicker Park's Myopic Books, one of the city's largest and oldest bookstores. The store's three floors are a bookworm's paradise.
Soak up some sun at one of the city's beaches along Lake Michigan (yes, Chicago has beaches). Two of the most popular are Oak Street beach and North Avenue beach.
Get down to some blues at Kingston Mines, one of the city's best blues club which also serves a full menu of BBQ options. The club stays open till 4 am on every night but Saturday, when it's open till 5 am.
Eat a Chicago style hot dog, which comes tucked in a poppyseed bun topped with relish, pickles, tomatoes, onions, and mustard. It's an unwritten rule that you shouldn't order your hot dog with ketchup.
Attend one of Lollapallooza's — Chicago's outdoor three day festival that runs from July 31st to August 2nd — aftershows; it's a great way to see a favorite artists without having to deal with the crowds.
The aftershows for this year's festival haven't been announced yet, but the lineup has. Click here for Lollapalooza's 2015 lineup >