The Chicago Guide to Dating - Romantic Winter Dates

Ice Skating at Millenium Park

You don’t have to be a professional figure skater to enjoy this fun date. You will see that most of the skaters are just beginning, and if neither you or your date are very good then you will have fun learning together! I recommend going after 4:30 pm when it starts to get dark and the city lights come alive. The Michigan Avenue Christmas lights add a little romance to the whole experience.

The McCormick Tribune Ice Rink (located in front of Park Grill) is open daily from 10am to 10pm from mid-November to mid-March.

Ice skating is free, but renting skates costs $10.
Lockers are also available for $1. (Quarters only)

Horse Drawn Carriage Rides

You’ve probably seen these carriages around downtown many times. It seems like a touristy thing to do, but it can be enjoyable for locals too… especially if you’re sharing the ride with someone you care about. JC Cutters offers horse drawn carriage rides around downtown Chicago year round. Despite the cold, winter just may be the best time to take a ride with all the lights and decorations that are around the city during the Christmas season.

It’s not the most budget-friendly date. Half hour rides start at $40. Add $20 for every 15 minutes thereafter. At the end of the ride, your are expected to tip the driver 15-20%.

Reservations are welcome, but not always necessary. You can hire a carriage at the corner of Michigan and Chestnut.

Hours of operation are:
* 7pm to 12am Mon-Thurs
* 7pm to 12am Fridays
* 11am to 12am Saturdays
* 12pm to 11pm Sundays

Go on a Christmas Lights Tour

Drive around the local neighborhoods together with mugs of coffee and check out the light displays.

If you don’t have a car, there are several tours you can pay to go on. Just do a search for “Chicago Christmas lights tour” and you will come up with a bunch of different options.

If you don’t want to spend any money, head on over to Navy Pier for Winter Wonderfest and walk through their impressive lights and decorations display. They also have many winter activities that you must pay to do such as Christmas-themed rides and shows.

Make a Snowman Together

Chicago definately gets enough snow, so bundle up and go out and play! You’re never too old to make snowmen. If you have enough time, make a snow couple! It may be corny, but that’s what makes it romantic.

Make a Gingerbread House Together

This is a fun and relatively inexpensive way to spend some time together. All you need is a small box, some graham crackers, a can of frosting, and various types of candy. (A little glue might not be a bad idea either.)

Find a flat piece of cardboard or platter to set up the house on. Then glue or frost the graham cracker and stick it to the box to create the base of the house. After that, let your imagination run wild!

You can also purchase gingerbread house kits from most grocery or craft stores.

Take lots of pictures while making your house! They will be fun to look back on later!

Sledding

Illinois is pretty flat, but there are a few places that you can go for some decent sledding action. You can take two sleds and race each other down the hill… or you can share a sled if you want to be really close. Either way, it’s a fun way to spend an afternoon together.

Where to find sledding hills:

-Mt. Trashmore in Evanston (On Oakton)
-Soldier Field
-Montrose Ave at the lakefront
-Schiller Woods (on Cumberland, between Belmont and Irving)
-Dan Ryan Woods (87th and Western)

Stay In for a Movie and Cuddling

This is one of my favorite dates… it is so simple, but one of the best ways to spend quality time together. If it’s too cold to go out, just stay in! A movie, blankets, hot chocolate, and each other… the perfect recipe for a romantic evening.

If you’re going to stay in all evening, making dinner together would also be fun.

Board games are another good way to spend a night in.

Catch a Ride on the Holiday Train

I don’t know if this is worthy of an entire date, but the CTA holiday train is one of my favorite things about Christmas in Chicago! It rotates around the different colored ‘L’ lines so that everyone has a chance to ride it. Here’s the schedule for 2008:

November 22,23 — Red and Purple Lines
November 26,29 — Blue Line
December 2 — Pink Line and Loop Elevated
December 4,5 — Green Line and Purple Line
December 6 — Green Line
December 10-13 — Brown and Orange Lines
December 18 — Purple Line Express
December 19 — Red Line
December 20 — Orange Line
December 22 — Purple Line Express
December 23 — Yellow Line