10 Chicago Date Spots To Get Your Cozy On

Baby, it's cold outside — but that doesn't mean you and your S.O. have to hibernate until springtime. Seriously, while it's all too easy to hit the sofa and hail at the altar of Netflix, why would you want to when there are so many great local spots for you to cozy up at?
Whether that means snuggling up in an intimate booth at a new hot spot like The Revel Room or learning how to cook up a seasonal favorite at The Chopping Block, you’ve got plenty of options. Trust, these 10 awesome date spots will make you glad you left the nest and braved the elements.
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Photo: Courtesy of The Revel Room.
The Revel Room
Formerly Empire Liquors, this inviting cocktail bar in Wicker Park is the perfect spot to cuddle up during the colder months. Reminiscent of an English pub with its giant, cozy, red booths lining the walls and dim, intimate lighting, The Revel Room also boasts a library-esque room full of wooden blocks toward the rear. Other highlights include the seasonally appropriate adult beverages, like Vandermill Totally Roasted Cider with cinnamon roasted pecans and vanilla (we’re die-hard fans!), and live music from the likes of local musician Aly Jados. Seriously, we couldn’t dream up a cozier watering hole if we tried.

The Revel Room, 1566 North Milwaukee Avenue (between Damen and North avenues); 773-278-1600.
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Photo: Courtesy of Up Comedy Club.
UP Comedy Club
Second City’s answer to standup, UP Comedy Club is a cut above the rest with its Caberet-style interior minimum and state-of-the-art audiovisuals. Holding 285 guests, the shows are fairly intimate, so unless the spotlight’s on you or your significant other (avoid the front row at a comedy show at all costs!), you’ll be comfortable and relaxed. Dinner is available throughout the entire show, and there’s no drink minimum, so you can sip your wine or cocktail at your leisure. We give that a standing “O.”

UP Comedy Club, 230 North Avenue (between Wells Street and North Park Avenue); 312-662-4562.
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Photo: Courtesy of Dolce Casa Café.
Dolce Casa Café
You don’t have to spend a million dollars to have a great date night. Don’t believe us? Check out Dolce Case Café and catch up over a cup of Joe. With a real working fireplace and a menu full of warm, handcrafted coffee concoctions, you’ll be snug as a bug in a rug at this Lincoln Park gem. The exposed brick interior and Art Deco decor with rotating works only serve to add to its charm, and bites are locally sourced and made with organic dairy products.

Dolce Casa Café, 4947 North Damen Avenue (between Ainslie and Argyle streets); 773-506-0708.
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Photo: Courtesy of The Violet Hour.
The Violet Hour
If you really want to wow your date, The Violet Hour is your spot. With a “secret” door that blends into the building and is blocked by a wall of dark curtains, you’ll want a hand to grasp as you step blindly into the unknown. Like falling down the rabbit hole, you won’t be disappointed by the mysteries that wait on the other side.

Guests are only allowed in if table spaces are open, so you won’t be interrupted by the 20 people behind you vying for your spot at the bar. The cocktails are handcrafted by some of the best mixologists in the city, so might we suggest the James Beard-nominated “Juliet and Romeo” in the name of love and thirst?

The Violet Hour, 1520 North Damen Avenue (between Wicker Park and Pierce avenues); 773-252-1500.
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Photo: Courtesy of Anjali Pinto.
CH Distillery
Warm yourselves and your spirits at this new West Loop addition, CH Distillery — Chicago’s only grain-to-bottle vodka distillery. Tours are held every Saturday and every other Tuesday at 5:30 p.m. ($15), so you can see how your drinks are made before you settle into a booth together and enjoy a CH vodka, gin, rum, or exclusive-to-bar whiskey drink.

CH Distillery, 564 West Randolph Street (between Jefferson and Clinton Streets); 312-707-8780.
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Photo: Courtesy of The Music Box Theatre.
The Music Box Theatre
If it’s tried-and-true that you prefer, you can’t get much more classic than The Music Box Theatre. Built in 1929, the old-time theatre instantly brings back a sense of romantic nostalgia with its old-school marquee and rising red-curtained screens. The twinkling star ceilings don’t hurt, either. While they largely screen independent and foreign films, the theatre also plays old favorites like Stand By Me (midnight, November 29 and 30), as well as thrillers, like the original Swedish version of The Girl with the Dragon Tattoo (2 p.m., November 18).

The Music Box Theatre, 3733 North Southport Avenue (between Grace Street and Waveland Avenue); 773-861-6604.
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Photo: Courtesy of Bottle & Bottega.
Bottle & Bottega
Impress your date with your artistic skills as you create your very own masterpiece over a glass of wine at Bottle & Bottega. Guided by an art instructor and armed with all the materials you’ll need, you can hit up a public event or get private instruction. If you’re unattached, you might even meet the love of your life here, as Match.com hosts a mingling event at the space on November 13 from 6 to 9 p.m. The whole idea is to make you feel like you’re hanging out in a living room, so you can’t feel any more welcome here. Prices vary by class and the wine is BYOB.

Bottle & Bottega, 2900 North Lincoln Avenue (between Southport Avenue and George Street); 773-313-9133.
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Photo: Courtesy of Storefront Company.
Storefront Company
Sidle up to your sweetie at the chef’s kitchen counter at Storefront Company, which allows you to be engaged in your meal from start-to-finish. A six-course tasting menu ($89) is offered with or without wine pairings (an extra $55), but the experience makes it money well spent. Menus rotate seasonally, so be sure to check the website for the restaurant’s most current offerings. Oh, and did we mention chef Bryan Moscatello has a Michelin Bib Gourmand designation?

Storefront Company, 1941 West North Ave (between Milwaukee and Damen avenues); 773-661-2609.
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Photo: Courtesy of The Chopping Block.
The Chopping Block
Tired of the whole dinner and a movie shtick? Spice things up (literally) with a cooking class at The Chopping Block, then recreate your newly learned meals at home together. You can choose from demo classes (from $40), which are led by professional chef instructors and include generous tastings, or hands-on classes (from $75) that allow you to participate in each step of the cooking process and savor your own meal once you’re finished.

Try the upcoming Cozy Casserole demo (Lincoln Square, 10 a.m. to 12:30 p.m., $45), or December’s planned Southern Comfort Date Night ($80), which will include a feast of fried chicken, collared greens, cornbread, and apple pie. Warm food and full bellies equals the perfect recipe for coziness!

The Chopping Block, various locations.
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Photo: Courtesy of Webster's Wine Bar.
Webster’s Wine Bar
Webster’s is a great date spot on a normal night, but its “second story” evenings really up the ante. Located upstairs, away from all the hustle and bustle, you’ll be treated to an evening of stories acted out by the writers themselves with accompanying music. Each story night has a theme, whether it be heartwarming, romantic or scary (the theme on November 10 is Sixth Sense: Stories of Warning and Awakening), and Webster’s offers a wine flight pairing that is expertly timed with the story schedule. If you’re not interested in the flight, the menu selection is impeccable — this is, after all, the oldest wine bar in Chicago.

Webster's Wine Bar, 1480 West Webster Avenue (between Clybourn Avenue and Dominick Street); 773-868-0608.
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