Best Festive Date Night Ideas Around the South Loop

It may be cold outside, but you can warm things up with a festive date night in the South Loop. From blues to movies to beers, we’ve got some fun things to do with your favorite guy or gal.

You won’t be singing the blues when you see the legend himself at Buddy Guy’s Legends. January is the musician’s annual residency at his eponymous club. You can make a day of it with acoustic acts in the afternoon, and you’ll want to be there early anyway to reserve a table for the evening performance. They’ve got a menu featuring cajun cuisine and a full bar, too.

The sky’s the limit when you take your date to the Willis Tower. When you’re not gazing into each other’s eyes, you can gaze out at four states at the Skydeck observation lounge. Step out on The Ledge for a bird’s eye view of Wacker below. If you want to make it the penultimate date night, they’ve got proposal packages, too.

Dinner and a movie may be a cliche, but there’s a reason it’s such a popular date night option. This is especially true when you head out to Showplace Icon. Located in the Roosevelt Collection, this isn’t your typical movie theater. You can begin the evening with a craft cocktail in the bar and have American fare delivered right to your seat. You don’t even have to worry about kids, because they’ve got an adults-only section.

If you have a shared love of great beer, go on a South Loop brewery tour. You can start at Vice District Brewing for a pint and some food truck fare, then head down to Motor Row Brewing, followed by a stop at Baderbrau, a cool warehouse space lined with murals and serving modern pub dishes to go with that 10-flight of craft brews.