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Romantic Chicago: Keep each other cozy in the Windy City

Destination(s): Chicago

The Windy City can be harsh, but there are many warm and cozy places to snuggle up with your best bud. Spend the day enjoying each other's company in Chicago's northern neighborhoods without too time out in the cold. Good food, good movies, good music, and good surroundings are sure to make this day reap some good love. read more about Romantic Chicago: Keep each other cozy in the Windy City

Fireside Restaurant and Lounge

Fireside Restaurant and Lounge

  • 5739 N Ravenswood Avenue
  • tel:1 773 561-7433
  • Visit website
  • Chicago, 60660
Music Box Theatre

Music Box Theatre

  • 3733 North Southport Avenue
  • tel:773 871 6604
  • Visit website
  • Chicago, 60613
Green Mill

Green Mill

  • 4802 North Broadway Avenue
  • At Lawrence
  • tel:+1 773 878 5552
  • Visit website
  • Chicago, 60640

This is the absolute best place to see jazz in Chicago! The Green Mill is a former speakeasy from days of Prohibition, where it was the headquarters Chicago gangsters, including the infamous Al Capone. Also famous for being the location where Joe E. Lewis was attacked with a knife. The ornate, sophisticated, and dark atmosphere has not changed much from the old days, and neither has the music. It has definitely upheld its mission to uphold a "mix of down-to-earth friendliness and class." There are different regular acts every night, with Big Band swing on Thursdays, Sabertooth Jazz Qunitet on Saturday and Sunday after 1am, and even a Poetry Slam on Sundays.
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The Ardmore House

The Ardmore House