Chicago's 2018 Holiday Dating Guide

1. A Quarter-Mile of Ice Skating: The Ice Ribbon

The Maggie Daley Park Ice Ribbon has been compared to a Mario Kart track or a lazy river at a tropical resort, however, this quarter-mile-long, 20-foot-wide ribbon is purely for ice skating against the gorgeous backdrop of Chicago's skyline. The sloped loop, located in the heart of downtown Chicago, is unlike any other rink in the city. Complementing the ribbon are places to enjoy a cup of hot chocolate, rent skates, and scale the climbing wall. Only downside: It can hold up to 700 skaters at any given time, meaning the lines can be painfully long.
Where: Maggie Daley Park, 337 E. Randolph St, Chicago, IL 60601
Season: Late November, 2015 to March, 2016
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2. Christkindlmarket In The Daley Plaza

In Chicago's bustling Loop lies The Daley Plaza, where you find a little piece of tranquility and magic during Christkindlmarket. Stroll down the sidewalk of this German-themed market and you will find yourself in a fairytale. The market is dotted with vendors and their red and white striped awnings draped with luminous displays of Christmas lights. Visit the Bavarian Pewter, for example, and find speciality holiday ornaments from Munich, Germany. Then head over and try the original Sternthaler Glühwein from Nuremberg, Germany (hot spiced wine) and a savory strudel! 
Where: Daley Plaza, 50 W Washington Street, Chicago, IL 60602
Opening Day: Friday, November 20th, 2015
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3. Magnificent Mile Lights Festival

The BMO Harris Bank Magnificent Mile Lights Festival returns for its 24th year to offer a full lineup of activities, starting bright and early in the morning and continuing throughout the evening.
Where: The Magnificent Mile located at 401 N Michigan Ave, Chicago, Illinois 60611
When: Saturday, November 21st beginning at 11am
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4. Christmas Tree Lighting Ceremony

This year marks the 102nd Annual Chicago Christmas Tree Lighting Ceremony at Millennium Park!
Where: Millennium Park, 201 E Randolph St, Chicago, Illinois 60602
When: Tuesday, November 24th at 6pm
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5. Lincoln Park Zoo Ice Skating

Strap on your skates this winter with ice skating at Lincoln Park Zoo! The rink at the Farm-in-the-Zoo welcomes skaters to enjoy the ice under the romantic displays of lights draping across the rink. Bring your own skates or rent a pair at the Farmhouse, and warm up afterward in the Main Barn with hot cocoa.
Where: Lincoln Park Zoo, 2001 North Clark Street · Chicago, IL 60614
Opening Day: Friday, November 27th, 2015
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6. Lincoln Park Zoo Lights

Visit Santa and enjoy live ice carving demos, carousel and train rides, warm spiced wine, frosty lager and hot cocoa, holiday crafts, animal exhibit viewings and chats, holiday gift shopping and Ice Skating at Lincoln Park Zoo at the Farm-in-the-Zoo! Attend the opening night of ZooLights on Friday, November 27th, 2015 at 4:25 p.m. and witness the lighting ceremony at the Kovler Sea Lion Pool to kick off the festivities!
Where: Lincoln Park Zoo, 2001 N Clark St, Chicago, IL 60614
Opening Day: Friday, November 27th, 2015 at 4:25pm
Free admission - no ticket necessary! 
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7. Chicago Scene New Year's Eve Party At The Drake Hotel

What: Voted "Best Chicago New Year's Eve Party" by a number of media outlets, the annual Chicago Scene New Year's Eve Party at The Drake Hotel is over-the-top. With more than 2,500 guests dancing to Chicago's hottest DJs, four ballrooms, premium top-shelf liquor served at more than 40 fully staffed bars, a breathtaking balloon drop and a champagne toast at midnight, it is sure to please party goers. For the bespoke crowd, the hotel's New Year's Eve Black-Tie Affair at Palm Court will have you indulging in Chef's small plates, food station delicacies and drinks.
Where: The Drake Hotel, 140 E Walton Pl, Chicago, IL 60611
When: December 31, 2015; VIP opens at 8pm and General Admission opens at 9pm
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8. Make Mulled Wine and/or Hot Toddies

Feel like avoiding the crowds and staying inside the comfort of your home? We have something for that too. There's nothing better than a warm cup of mulled wine or a hot toddy when cool weather hits. This is a great second (or third or fourth!) date option when you want to get to know your date better. Trying a new recipe with your date is a great way to learn or improve a skill together which enriches your bond and gives you lots to talk about. Furthermore, coinciding a date with an activity allows for a more relaxed state in which to converse since both people are actively involved in performing a task together.