Romantic Christmas Date Spots in Chicago (2025)
Chicago is a beautiful city known for its cold winds and snowy winters. Yet, with the onset of the season's crisp chill, holiday festivities and activities pop up all over the city, perfect for holiday date ideas. Whether you're looking to brave the cold with an active date night out gliding hand-in-hand across ice skating rinks nestled in picturesque parks heading on a tour amidst dazzling holiday lights, or find warmth on a romantic night in to savor quiet moments and get cozy at a festive themed pop-up or hidden rooftop treasure, there are plenty of options to choose from. Chicago's diverse holiday offerings ensure the perfect holiday date for any preference.
See The Lights
Chicago is known for its beautiful holiday lights displays that create a magical atmosphere and a perfect setting for a romantic date. Here are some of the best places to see the lights in Chicago.
1. Lincoln Park Zoo
Lincoln Park Zoo is one of the most popular attractions in Chicago and it becomes even more magical during the holiday season. Offering free access on Mondays, the zoo is decorated with over two million lights, creating a winter wonderland that is perfect for a romantic stroll. Visitors can see the animals and enjoy the light displays, ice skating, and holiday markets.
2. Lightscape At Chicago Botanical Garden
Lightscape at Chicago Botanical Garden is a breathtaking light show that transforms the garden into a magical wonderland. Visitors can walk through the illuminated gardens and experience the beauty of nature in a new way. The show features thousands of lights, projections, and interactive displays that create a unique and unforgettable experience.
3. Illumination: Tree Lights At The Morton Arboretum
Illumination is a stunning light show that features over one million LED lights. Visitors can walk through the illuminated trees under canopies of twinkling lights. The show features interactive displays, projections, and synchronized light and sound shows that create a magical atmosphere.
Wander The Christmas Markets
Wandering through one of Chicago’s Christmas markets is the perfect way to get into the holiday spirit. Here are some of the best markets to check out:
1. Christkindlmarket
The Kindlmarket downtown is one of the biggest and most popular Christmas markets in Chicago. Located in Daley Plaza, this market features over 50 vendors selling everything from German sausages and hot spiced wine to handmade ornaments and toys. Visitors can also enjoy live music and entertainment, as well as a large Christmas tree and a giant German cuckoo clock. The market is open daily from late November through Christmas Eve.
2. Jack Frost Christmas Pop-Up Market
The Jack Frost Christmas Pop-Up Market in Fulton Market is a newer addition to Chicago's Christmas market scene, but it's already become a favorite among locals and visitors alike. This market, spread over 2 acres, features a unique outdoor experience with a curated selection of vendors selling unique and handmade gifts, ice skating, ax throwing, bumper cars as well as food and drinks from some of Chicago's best restaurants and bars.
3. Light Up The Lake
Light Up The Lake at Navy Pier is a seasonal market event including activities including ice skating, live music shows, an artisan marketplace, and a cozy fire pit more warming up and making s’more. The famous 200-foot Centennial Wheel at Navy Pier is also illuminated and features fully enclosed and heated gondolas for a comfortable cozy ride with views of the city and lake.
Ice Skating
Chicago is famous for its cold winters, but that doesn't mean you have to stay indoors. Ice skating is a fun and romantic way to enjoy the winter weather, and there are plenty of rinks to choose from in the city.
1. Millennium Park
The rink in Millennium Park is located in the heart of downtown Chicago and is one of the most popular ice skating destinations in the city. The rink is surrounded by the city's iconic skyline and is open from November to March. Skating at the Millennium Park Rink is free, but skate rentals are available for a fee.
2. The Skating Ribbon At Maggie Daley Park
The Skating Ribbon at Maggie Daley Park is a unique ice skating experience that winds its way through the park's landscape. The ribbon is 1/4 mile long and offers skaters a chance to enjoy the park's scenery while skating.
3. Midway Pleasance In Hyde Park
The Midway Pleasance in Hyde Park is a neighborhood park that features a small ice skating rink during the winter months. This rink is perfect for those who want to enjoy a more low-key skating experience.
4. Gallagher Way Rink In Wrigleyville
The Gallagher Way Rink in Wrigleyville is located just steps away from Wrigley Field and is open from November to March. The rink features a cozy warming house and skate rentals are available for a fee. This rink is perfect for those who want to combine their love of ice skating with their love of sports.
5. The Peninsula Sky Rink
The Peninsula Sky Rink is a unique ice skating experience located on the 5th-floor terrace of the Peninsula Chicago Hotel. The rink offers stunning views of the city and is open from November to February. Skate rentals are available, and the rink is reserved exclusively for hotel guests on weekends.
Cozy Up at a Holiday Pop-Up Bar
Chicago is famous for its holiday pop-up bars that offer unique and festive experiences. Here are some of the best festive bars great for a cozy holiday date night.
1. Santa Baby Christmas Bar
The Santa Baby Christmas Bar in Wrigleyville is a perfect place to enjoy the holiday season with your special someone. This bar is decorated wall-to-wall with Christmas lights, ornaments, and other festive decorations. It offers a wide range of drinks, including holiday-themed cocktails such as the Tropical Sleigh Ride and Moet Mistletoe as well as festive dishes like Santa's Sliders.
2. Frosty’s Christmas Bar In River North
Frosty’s Christmas Bar in River North is another popular holiday pop-up bar in Chicago if you’re looking for some big holiday energy and a party of a date. The bar is decorated with snowflakes, icicles, and life-sized toy soldiers across 3 floors, 4 bars, and 2 dance floors. Dance the night away while sipping themed cocktails under the twinkling lights.
3. Elf’d Up
Elf’d Up in Wrigleyville is a unique holiday pop-up bar that is inspired by the movie Elf. The bar is decorated with more than 1,000 elves, Christmas trees, twinkly lights, paper snowflakes, and other festive decorations straight from the movie. You and your date can go wild and share a plate of Buddy's breakfast pasta, a combination of spaghetti, maple syrup, chocolate syrup, mini marshmallows, and strawberry pop tarts, or try a beer served in a 36oz elf boot.
4. 8 Crazy Nights
8 Crazy Nights is a Hanukkah-themed pop-up bar that celebrates the Jewish holiday. The bar is decorated with over 14,000 blue and white lights, menorahs, dreidels, and a wall of Hanukkah sweaters. It offers a variety of drinks, including holiday-themed cocktails, and a variety of themed food options, including latkes and matzo ball soup.
5. Rudolph’s Rooftop At LondonHouse Chicago
Rudolph’s Rooftop at LondonHouse Chicago is a unique holiday pop-up that offers a romantic and cozy experience with the Chicago skyline as your backdrop. The bar features heated igloos on the 22nd-floor terrace that are decorated with twinkling lights, snowflakes, and ornaments. It offers a variety of food and drinks, including spiced mulled wine, colorful charcuterie boards, and festive gourmet dishes.
Amidst the frosty winds and snowy landscapes, Chicago presents an abundance of opportunities for love during the holidays. These festive activities are perfect for chance encounters, fostering new connections, adding some romance to a first or second date, or for couples to create cherished memories and share the warmth of the season. Whether it's a serendipitous meeting during a stroll through a lightscape, a heartwarming conversation over hot cocoa at a Christmas market, or the shared laughter while attempting your first glide across an ice rink, Chicago's holiday offerings provide moments to spark new relationships or deepen existing bonds, immersing everyone in the joyful spirit of the season.