10 Winter Date Ideas: Chicago

When we asked readers what was the best city to find 10 winter date ideas, Chicago was among the first on everyone's lips. They don't call it The Windy City for nothing. In those frigid Christmas months, when it comes to winter date ideas, Chicago really is the town that won't let you down. With so much happening all over the city, planning that perfect date is hardly a task. Here are ten winter date ideas that are sure to have those Chi-Town cuties wanting to snuggle up on those cold winter nights.

  1. Skate on State – Outdoor ice skating in the heart of the loop—show off your skating skills! Placed under an eight story Christmas tree for romantic holiday ambiance, this winter date idea is sure to melt some ice. Better get that mistletoe belt handy!
  2. Michigan Avenue Christmas Stroll – Ah, the magnificent mile. One full mile of Chicago architecture, upscale shops, department stores, and festively decorated store windows. Take your lady for a romantic stroll down Michigan Avenue at Christmas time, and she'll think you are sentimental and traditional, and never know that you're being cheap. Because it is free, it's one of the best winter date ideas in Chicago. Chances are she'll need some warming up before long. Score!
  3. Sledding – Chicago has many parks and forest preserves with large hills that are fabulous for sledding. Grab a basket of snacks, a thermos of hot cocoa (or better yet whiskey), and set out on a winter picnic! Once the two of you head down that snowy hill on your sled at high speed she'll be straddling you and holding on tight! If there's whiskey in your thermos, she may be doing that when you get home too!
  4. Bears Football Game – If you are fortunate enough to be dating a sports fan, here's a great winter date idea! Chicago Bears games are a great place to share your love for football, and maybe your love for each other while you share a beer and blanket in those cold, cold bleachers. Go team!
  5. Blackhawks Game -Some girls just don't like cold weather, but you can still enjoy winter sports (and perky nipples) with us. Indoor hockey games are a great winter date idea. Chicago Blackhawks games have enabled many lucky guys to be "high sticking" at the end of their dates.
  6. Glow in the Dark Miniature Golf – Most girls love miniature golf. When it's indoors in a pitch black room with black lights and florescent decor, you've got it made in the shade. The indoor glow golf courses are seemingly designed for dating with their 1960's psychedelic "free love" ambiance.
  7. Museums – If you are dating a gal who is more culture than sports minded, here are your best winter date ideas. Chicago is famous for its museums and cultural centers. Try the Shed Aquarium, the Museum of Science and Industry, the Field Museum, Art Institute, or Planetarium. Take a day trip and tour them all. You'll be sure to score some smarty points and get you some intellectual lovin'!
  8. Brew and View – This is great! Definitely a win-win winter date idea. A movie theater with beer and cocktails. Who could ask for more? Even if you get roped into a chick flick, you can drown your sorrows in alcohol and still come out looking like Mr. Sensitivity.
  9. Casino Boats – Whether you like gambling or not (you're already gambling on whether you'll get some or not), the casino boats are always a great winter date idea. Chicago has a few of these betting boats located just out of city limits. Take your lady on a nice drive to the outskirts of town, give her a few bucks to play games with, and tell her over the evening view of the river that she's your Queen of Hearts. Maybe you'll get lucky.
  10. Indoor Water Park – The best winter date idea of all! With a hotel and indoor pools, one way or the other, you'll get her out of her clothes!

 

 

 

 

 

 

 

 

 

 

 

 

 

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