Chicago Date Ideas Overview

The Barrelhouse Flat - Cocktail Bar | Lounge in Chicago

Planning a date in Chicago? Well, it’s almost not fair how easy it is. In a city teeming with classy cocktail lounges, music venues, comedy clubs, and world-class restaurants, it is nearly impossible to go wrong.

Those hoping for a romantic date should head to the Signature Lounge on the 95th floor of the John Hancock Building, where they can sip cocktails and enjoy sweeping views of the city skyline. Afterwards, enjoy an exquisite meal at one of Chicago’s world-famous restaurants, such as Aviary or Girl & the Goat, which offers a fantastic foodie experience for those who love to eat.

Looking for something more casual? Chicago blues clubs offer a laid-back experience and unbeatable music on most nights of the week. Check out B.L.U.E.S. in Lincoln Park or Buddy Guy’s Legends in the South Loop for a relaxed date experience that is sure not to miss. Chicago is also home to hundreds of music venues across a variety of genres, so hipsters can take their sweethearts to Metro while metalheads enjoy date-night at The Mutiny.

Hipsters and cocktail-lovers should head to The Violet Hour for a romantic date. Or if the line is too long, try The Whistler, which also serves up classy cocktails and offers live music or DJs nearly every night of the week. Beer nerds can bring their dates to The Map Room, while whiskey-lovers should head to Fountainhead for an extensive scotch list and mouthwatering mac & cheese.

And of course, for those at a complete loss, it’s impossible to go wrong with a Second City show. A late night of laughs at this Chicago institution is sure to earn anyone a good night kiss.

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