If the weather is nice (or if it's chilly and you are feeling brave), take a 75-minute architecture boat tour down the Chicago River. There are several tour companies to choose from, but our favorite is Shoreline Sightseeing with multiple tours leaving from Michigan Avenue and Navy Pier daily. A perfect way to see the city... we cannot recommend this enough!

Need a laugh? Check out a show at The Second City, the world's premier comedy club, comedy theater, and school of improvisation. Who knows? You might even spot a famous alum!

We would suggest a trip to the South Side to see the White Sox, but they are out of town and also very bad. Instead, venture up to Wrigleyville and check out a Cubs home game at the Friendly Confines, the 2nd oldest ballpark in the majors. For extra fun and your chance at spotting an infamous beer snake, sit in the bleachers. Stop in at Merkle's Bar (the location of Kelly & Chris' first date!) for a pre-game drink.

Belt your heart out and win over the crowd at the best karaoke spot in the city, Louie's Pub: the Place Where Friends Meet.

An upscale New American restaurant in West Loop where Stephanie Izard (the 1st female chef to win Top Chef!) serves up innovative small plates from a dramatic open kitchen.

Enjoy a creative seafood & pork-focused menu plus global brews in a hip setting with communal tables.

Intimate basement wine bar in a century-old building with a vintage vibe and New American cooking. Directly across the street from Hyatt House.

50,000-sq.-ft. industrial hub for chef-driven eats & cocktails with communal seats & a rooftop deck.

Gourmet burger joint that names all menu items after heavy metal bands. Great beer list too!

"No fries – CHEEPS! No Pepsi – COKE!”

Low key burger spot located under Michigan Avenue and a Chicago landmark. For the best possible patty-to-bun ratio, get the double cheese. Trust us. Feeling brave? Wash down your burger with a Chicago handshake.