Eat

Billy Goat Tavern

A supposed curse on the Cubs and a classic Saturday Night Live sketch made the Billy Goat Tavern famous, but the cheeseburgers keep people coming back.

430 N Michigan Ave
Chicago, IL 60611

Eat

The Diner Grill

An impossibly no frills, old-school diner famous for the infamous Slinger – a concoction of chili, eggs and hash browns. Eat it in a single sitting, and you get a time-stamped certification of completion (for most people, around 3:30 a.m.).

1635 W Irving Park Rd
Chicago, IL 60613

Sleep

Inn of Chicago

This stylish hotel is just half a block from Chicago’s famous Magnificent Mile. Check out the Skyline Terrace on the 22nd floor for breathtaking views of the city.

162 E Ohio St
Chicago, IL 60611

See & Do

Kingston Mines

Kingston Mines is the club that brought the blues to Chicago's North Side. Voted Best Blues Club in Chicago, music is played here 7 nights a week. The club also features Doc's Rib Joint, which serves up the city's best late-night barbecue.

2548 N Halsted St
Chicago, IL 60614

Eat

Paddy Long's

This unassuming neighborhood pub holds a delicious secret for those in the late-night know: a menu full of the biggest and best bacon dishes you’ll find anywhere—especially at 1 a.m.

1028 W Diversey Pkwy
Chicago, IL 60614