by Mason Johnson

Last we spoke, I was telling you all the best spots in Wicker Park you could go to have a date. I want you to know, a lot has changed since then. I’m not the amateurish schmuck I was when I wrote that dating guide. I’m a totally new schmuck. I went out in the wide world and found what is called a library. From there I read up on everything dating: the opposite sex, the same sex, sex in general…

… it was all very confusing.

Still! Confused or not, I feel like I’ve become a better person because of it. So here I am, more mature, ready to tell you what the best darn winter date spots are in this fine city of ours.


Holiday Train


If your date happens to be during the holiday season, you have to ambush your significant other with a ride on the holiday train. Even if the idea of a train bespeckled in holiday cheer makes you want to jump off a cliff and into an acid-filled ocean, you should do it, simply because it’ll reveal much of your date. If it seems like they’d happily jump into the acid-ocean hand-in-hand with you, then you know it’s meant to be. If, on the other hand, they decided they love the holiday train, then I suggest ditching them there. Forever. Some things aren’t meant to be.

Check out this detailed schedule to see when the holiday is running on your line!


Hours & Pricing

People occasionally like to do stuff outside. Yeah, I don’t get it either. Anyways, one of these things is ice skating. Take the holiday train to Wrigley Field and check out the ice skating rink that exists in the parking lot throughout the winter.

Pro-tip: feign that you’re bad at skating so your date has to guide you on the ice by holding onto your hips. This is especially attractive if you’re a man, chicks dig men with humility.

:( (credit:

Garfield Park Conservatory makes the best out of the outside, by keeping it inside.

I think that makes sense.

Anyways, for a nature-filled escape from Chicago’s torturous winter check out the Garfield Park Conservatory. Filled with all kinds of foliage, ponds, and all sorts of other things you nerds will probably love, it’s a great place to have a stroll.

The Garfield Park Conservatory could also use your help, while you’re there. This summer, damage from hail closed many of their exhibits and gardens. Even now, many months later, the damage isn’t totally repaired. To see how you can help, check out the One Pane At A Time program they’ve set up.

Nana is one of those all organic, hippy dippy sorta places, if ya know what I mean. But! It’s also one of those places that serves really good food. They appeal well to those of us who are vegetarians (which is why it was probably included in our Best Vegetarian Restaurants Guide), but also has a lot to offer to the meat eaters out there. This place literally made one of the best burgers I have had in, like, a bajillion years. Adding a fried egg and maple-dijon bacon was a great idea.

So yeah, if you’re not sure about your date’s eating habits, this is a good place since they provide something for everyone. Oh yeah, they’ve got great cocktails also. Now you have to go.

Photo Credit: Christkindlmarket Chicago

I don’t know what the heck gluhwein is, but I know I like it. Plus, you get to drink it out of a mug shaped like a stocking that you can keep! All I’m saying is that the Christkindlmarket is one of the best excuses to afternoon drink in the winter. Throw in some potato pancakes, a sausage or two, and a hawt date, and I’m good to go.

To find out more about the Christkindlemarket, check out our guide on it!

(credit: Tim Boyle/Newsmakers)

Fight a Polar Bear

Polar bears are known world-wide as kings of the snow, the masters of winter. They are the ultimate winter predator, which is why beating one up* would be the single most impressive thing you could do in front of your date. If all the other activities in this list fall flat, then you really have no other choice. Unless you want your date to think you’re a loser, that is. My advice: use your speed and agility, the polar bear is a strong, but slow, beast. Use it’s slow, lumbering movements against it. Then, when the time is right and le polar bear is tired, strike with your lightning quick reflexes.

Trust me, you will be worshiped as a king.

You’re welcome.

*After seriously contemplating what my lawyers might tell me if they read this, I’ve decided to include a small message to everyone out there considering punching a polar bear: don’t. It’s a bad idea. Seriously.

Mason Johnson, CBS Chicago