10 Cool Date Ideas For Cool Winter Nights

Photo: Roman Samborskyi / Shutterstock
man and woman walking in snow

Winter nights don't have to be frigid and uninspiring. In fact, they can actually be more romantic than — Ohhhh, those summer nights — (to quote Grease).

Something about the chill in the air makes a perfect excuse to grab your honey, get close, and create your own warmth: whether it's by cozying up fireside, digging into a piping-hot dinner of comfort food (fact: calories don't count in the winter; I don't make the rules), or warming up your hands with a hot toddy.

To get the winter wheels rolling and avoid the seasonal blues, we've gathered ten cool date night ideas for cool, cozy nights in Chicago:

1. Stay at the North Pole — almost

What is it? Each year the 2,000-square-foot Presidential Suite at the Swissotel Chicago is transformed into Santa’s home-away-from-the-Pole for the holiday season featuring over-the-top décor and numerous glistening Christmas trees complemented by sweeping views of the magical cityscape.

What to try? Wake up to daily breakfast and cozy up with the kids, in the comfort of your own space, with toys and games, holiday crafts, letter writing to Santa, cookie decorating, and a build your own Swiss Hot Cocoa bar. For those on a budget, the Elf Decorated Room Package is less expensive — and just as fun and festive.

Why it's a great date spot: For the couple who absolutely goes ga-ga for Christmas, there's no better fully immersive holiday experience. 

2. Live the Santa Baby song IRL

What is it? A multi-level, multi-room, over-the-top Christmas experience, complete with a full-sized '54 convertible — ala the song — smack dab in the middle.

What to try? You're a yummy one, Mr. Grinch: a green (what else?) twist on the classic margarita with Hornitos tequila. 

Why it's a great date spot: There's so much to look at (the full-sized gingerbread men! the ugly sweater wall! the ornament ceiling!) it's conversation-starter central.

3. Visit the most authentic German Christmas market outside of Europe

What is it? The Christkindlmarket is the most authentic traditional holiday market of its kind outside of Europe, offering traditional German gifts, local artisans, and most importantly: German beer.

What to try? Stuffed pretzels, baked cheese, schnitzel — and don't forget to grab a mug of glühwein (traditional hot spiced wine) in the annual Christkindl souvenir mug (they change the design every year — they're collectibles!)

Why it's a great date spot: Given Chicago's cool temps — and that most of the market is outdoors — it's a great excuse to link arms and cozy up. *wink*

4. Indulge in boutique sushi

What is it? A contemporary take on traditional sushi and Japanese Izakaya from Chef Jordan Dominguez, the chic lounge/restaurant will make its home in the lobby of the Claridge House in the Gold Coast.

What to try? Stand-out apps include Japanese sweet potato chips and bougie tartare; as for signature maki, try the 12:44, Moonwalk, and Chicago rolls. 

Why it's a great date spot: The menu is built to be a shareable dining experience, with items that pair seamlessly with their exquisite cocktail and martini program. Also, it's a quiet enough restaurant to actually have an in-depth conversation.

5. Dip into fondue & smores at a firepit table

What is it? Consider this your own personal Frozen moment. Nestled between Millenium Park and The Magnificent Mile, The Fairmont Chicago has completely transformed itself this winter into a rustic lodge fit for a Northerly ice Queen or King.

What to try? Chef William Schultz completes the experience with a seasonal menu of wintery-themed bites like Sweet and Savory Fondue and S’mores and Oaxaca Spiced Short Ribs. Signature hand-crafted cocktails include a Flaming Egg Nog made tableside and Oh So Delish Hot Chocolate.

Why it's a great date spot: It's such a great date spot that the lodge is hosting entire events connecting local singles from the LGBTQ community in celebration of the holiday season.

6. Spend a weekend at an Olde English inn

What is it? For a romantic getaway straight out of a storybook, couples who book Deer Path Inn’s new Romantic Retreat experience will be treated like royalty from the moment they check into their graciously appointed luxury suite. Couples can also request a rose petal turndown service to take the romance factor up a notch. 

What to try? Don't miss the chance to elevate your breakfast experience with an opulent brunch spread in the elegant English Room or the mixology class with Jorge at the White Hart Pub: he's truly a world-class cocktail master (and has awards to prove it). 

Why it's a great date spot: If you're in need of comfort, a reboot on romance, and a truly unmatched standard of sophistication — and what new parent isn't? — both in the accommodations and in the service itself, a weekend of pure bliss awaits you.

7. Glamp till your heart's content

What is it? Luxury camping AKA glamping overlooking Wrigley Field at Hotel Zachary? Sign us up! Within signature canvas tents, you and boo can relax on comfy couches and enjoy cozy festive décor, complete with hot toddies and fire cauldrons to stay warm. Don't forget to pack your plaid — the luxuriously snug tents are an Instagrammer's winter paradise.

What to try? A selection of barreled, large-format cocktails including the 'Oaxacan Old Fashioned' with reposado tequila, mezcal and notes of chocolate and mole bitters as a riff on the classic, and the 'El Diablo Gone Camping', an iconic tequila cocktail with crème de cassis, lime and ginger beer.

Why it's a great date spot: The whole glamp-y vibe is cozy-chic and uber-romantic. Cuddle close in the tent and heat your outsides by the fire, while warming up your insides with a toasty drink.

RELATED: 8 Super Sweet Ways To Bring Romance Back To Your Relationship

8. Soak in an ancient thermal bath

What is it? Inspired by the tradition of baths from ancient Roman, Greek, and Ottoman civilizations, AIRE ancient bath experiences all take place in restored historical buildings in the center of cities: currently New York, Chicago, Barcelona, Sevella, Almería, and Vallromanes. 

What to try? The 'Escape Together' package, which in addition to the thermal bath circuit includes a 45-minute relaxing couples massage and features hot compresses designed to release muscle tension and relax the mind.

Why it's a great date spot: Dim lighting. Warm baths. Candles. Custom couple's experiences are built around romance and enchantment

9. Pair steak night with a show

What is it? Pair a hearty dinner and a show. Stolp Island Social is a seasonal kitchen and steakhouse offering a warm, relaxed atmosphere, with a vibe reminiscent of 1920s Aurora meets Coco Chanel. Adjacent to the restaurant is the award-winning Paramount Theater, which has been open since 1931 and is iconic for its impeccably-preserved art-deco architecture and Broadway-quality productions.

What to try? Obviously, the steak. But beyond that, it's hard to go wrong anywhere on this Amy Morton-approved menu (yes, that Amy Morton of famed Morton's Steakhouses) but we recommend the kale salad, the whole roasted branzino, and the deviled eggs —​ all paired with a glass of vino, of course. 

Why it's a great date spot: It's a classic crowd-pleaser twofer that appeals to everyone, plus it's the traditional dinner + a play —​ only elevated and extremely elegant.

RELATED: 21 Couples Share Their Amazing, Atypical Honeymoon Destinations

10. Nom on gnocchi straight from the southern region of Italy

What is it? Osteria Trulli, an authentic Pugliese kitchen located in Arlington Heights, IL. Focusing on “La Cucina Povera” (cooking of the poor), executive chef, long-time restauranteur, and Puglia native Giovanni DeNigris celebrates his passion for the humble coastal cuisine that defines one of Southern Italy’s most brilliant regions.

What to try? The homemade gnocchi with black truffle cream is the best gnocchi outside of Italy I've ever had the pleasure of eating. The panzerotti (calzones filled with cheese and mozzarella sauce) are like little pockets of piping-hot love in your mouth. And don't dare to even consider walking out the door without devouring the mini cannolis — share one if you're too full of pasta (we wouldn't blame you.)

Why it's a great date spot: Not only is it comfy and intimate — two adjectives ideal for the making of any great date night — the restaurant truly feels like home

RELATED: 4 Tips To Plan The Perfect Romantic Dinner Date At Home

Andrea Zimmerman is the editor-at-large at YourTango covering lifestyle, relationships and more. Follow her on Instagram