5 Quirky Date Night Destinations in Chicago

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Date night doesn’t have to be the same each time. While we all love cuddling up at the movies or trying new restaurants or embracing a bit of high culture at museums, every once in a while, date night needs to be shaken up. Each city has a hidden world of strange, quirky, and delightful things to do. Try any one of these on your next date night and embrace the weird, whimsical part of life.

Woolly Mammoth Antiques & Oddities

A tour through Woolly Mammoth Antiques & Oddities is nothing like your typical trip to the Antique Shop or Flea Market. The shop is a wonderfully curated collection of whimsical, eclectic items. You can wander through the shop laughing at its oddities, including taxidermied squirrels, antique medical equipment, art of all styles and more. Stepping into the shop may feel like stepping into an entirely different world – a quirky one made for exploring. 

AIRE Ancient Baths

A hidden gem of Chicago that will remind you of the ancient baths found throughout Europe. But this bathhouse/spa was built from a restored factory that dates back to 1902. Among the industrial architecture of early 20th-century Chicago you’ll relax in the same way the Ancient Romans, Greeks, and Ottomans did. This is not your traditional spa experience and makes for a unique, restorative evening out. Try the Wine Bath Experience for Two. 

Great Train Story Diorama

Rediscover your childlike wonder and joy at the Museum of Science and Industry. You and your date can tour through 1,400 feet of model train railroad tracks, an entire world in miniature size. The entire diorama represents more than 2,000 miles of the United States from Chicago to Seattle. The details are remarkable and something which you and your date can marvel at for hours.

Turtle Racing at Big Joe’s

Fancy a little competition at a local watering-hole? Try the darts or play a round of pool at Big Joe’s – or cheer on a few adorable creatures during Table-top Turtle Derby. Big Joe’s offers a night out like any other, where you can cheer on a little turtle as it “runs” its heart out. It may be quirky and unusual but that’s why we love it.


It may be one of the strangest winter sports – played with large stones and brooms – but is also fabulously fun. Head to Kaiser Tiger, Whiskey Business, or Upstairs at the Gwen to try your hand at curling. Your date can slide the stone, while you frantically sweep in front of it to clear the ice and make it slide faster. The best part is when one of you, inevitably, slips and falls on the ice. Several places in Chicago offer adult leagues where you can curl, drink, and have an opportunity to perfect your skills while switching up the typical date night. 

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