9 holiday date nights that sleigh

Between family get-togethers, shopping for gifts and endless errands, the holidays can sometimes feel more stressful than enjoyable. Before you turn into a full-on Scrooge, grab some one on one time with your partner and celebrate the season at these fun area events. 

Go shopping at Randolph Street Market’s Holiday Market.

When: Nov. 23-24 and Dec. 14-15

Where: Randolph Street Market, 1341 W. Randolph St., Chicago

Cost: Tickets start at $8

If you can manage to squeeze in a day date, the Holiday Market makes for a fun day of shopping, sipping and getting into the Christmas spirit. Check out 125 booths of handmade and vintage goodies with your sweetheart while enjoying complimentary Captain Morgan and Baileys cocktails. Make sure to utilize the free coat and package checking so you can hang worry-free all afternoon.

Take a night stroll at Illumination: Tree Lights at Morton Arboretum.

When: Nov. 23-Jan. 5

Where: Morton Arboretum, 4100 Illinois Route 53, Lisle

Cost: Tickets start at $18

Is there anything more romantic than strolling with your sweetie looking at twinkly lights? Illumination more than exceeds your average holiday lights exhibit with colorful, interactive lighting displays, eye-popping digital projections and seasonal music along a one-mile path. Drink stations are set up throughout the trail and fire pits are available for roasting marshmallows (also a perfect spot for sneaking a smooch when your toes are inevitably freezing).

Enjoy holiday cheer along the Southport Cocktail Crawl.

When: Dec. 6

Where: 3505 N. Southport Ave., Chicago

Cost: Tickets start at $30

This event features special deals from local shops and live entertainment, then grab your ticket and enjoy some spirits at the Cocktail Crawl along Southport Ave. Included in admission is a special tasting glass and 15 different holiday specialty cocktails from businesses along Southport Avenue.

See the ZooLights and drink beer at Lincoln Park Zoo’s BrewLights.

When: Dec. 12

Where: Lincoln Park Zoo, 2234 N. Cannon St., Chicago

Cost: Tickets start at $20

Most visits to the zoo with your partner probably include hauling strollers and sippy cups around while trying to keep your screaming toddler from making a break for the monkey enclosure. Take the night off from parenting and enjoy an evening of beer sampling instead. General admission tickets include 12 samples of craft, seasonal beers, a tasting mug, live music and a delightfully child-free ride on the carousel. 

Watch your favorite Christmas movies

When: Dec. 12-24 (Select dates)

Where: Music Box Theatre, 3733 N. Southport Ave., Chicago

Cost: $15.50 for single feature, $24 for double feature

Music Box Theatre is beyond swoon-worthy and the perfect place to spend a chilly Chicago night with your love. Curl up and enjoy two beloved holiday films — It’s a Wonderful Life and White Christmas (which is a sing-a-long feature) at this annual Christmas event. Then, make the babysitter stay late so you can chat over a cocktail at Music Box’s lounge.

Take a helicopter tour with holiday lights.

When: Nov. 30-Dec. 31

Where: Departs from 2420 S. Halsted St., Chicago

Cost: Tickets start at $164.99

If you’re looking for a date night that goes above and beyond (literally), take a helicopter ride around the city to see some of Chicago’s most well-known attractions covered in holiday lights. Yes, the price is definitely a splurge, but getting a bird’s eye view of Willis Tower, Lincoln Park Zoo, Navy Pier, Wrigley Field and Soldier Field is truly a magical, once-in-a-lifetime experience.

Go ice skating at Millennium Park.

When: Nov. 15-March 8 (weather permitting)

Where: McCormick Tribune Plaza & Ice Rink, 1 N. Michigan Ave., Chicago

Cost: Free, ice skate rental available for $13 and up

Create your own romantic scene straight out of Serendipity by spending an evening skating with your other half. Sure, you may look like stumbling fools at first, but at least you’ll be doing it together. Pro tip: arrive earlier in the evening to avoid having to wait in a long line. After you skate, warm up by grabbing dessert across the street at Cindy’s.

Enjoy festive cocktails at Frosty’s Christmas Bar.

When: Nov. 22-Jan. 5

Where: 809 W. Evergreen Ave., Chicago

Cost: Tickets start at $15

If you’re looking for a bar that is all about the holidays, this pop-up bar in Lincoln Park is it. Three floors are decked out in sparkling lights with large ornament chairs and holiday decor. Cheery tunes are playing, the big, jolly man himself is making merriment and holiday cocktails include eggnog with gingerbread cookies.

Bounce in your seats at Q Brothers Christmas Carol.

When: Nov. 28-Dec. 23

Where: Chicago Shakespeare Theater, 800 E. Grand Ave., Chicago

Cost: Tickets start at $32

This hip-hop take on the Dickens classic is pumped with sharp wit and a DJ beat that will have you loving this new version more than you could have imagined. This hilarious and heartwarming show will brighten your holiday season. 

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Cortney Fries
Cortney Fries
An award-winning travel journalist, Cortney Fries (pronounced "freeze") has been writing about family travel for over a decade. She knows that parents planning trips are looking for all members to have fun and make lasting memories. Cortney believes that you should definitely try anything that makes you slightly nervous.
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