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Valentine’s Day Date Guide 2017: CHI

Love is in the air! Whether you have plans with your S.O., a Galentine’s Day bash, or were planning on Netflix and chilling, we have ideas for how to celebrate the sappiest holiday, however you see fit!

Treats for your sweetheart

Glazed & Infused
If your sweetie loves sweets, then pick up the doughnut fondue platter box at Glazed & Infused to treat your honey (or yourself, LBH) to a sugar coma that everyone deserves once in awhile. For more information, click here.

Pie, Pie, My Darling! Pop-up
Cookies without all the additives? Yes, please! Head to the second annual Valentine’s Day Pop-up of Pie, Pie, My Darling! at Kitchen 17 in Lakeview. Cookies, cakes, cupcakes, brownies and more will be available at this pop-up, but they certainly won’t last long! Afraid of them running out? Pre-order by sending in your order to For more information, click here.

Staycation Relaxation

Le Meridien
Want to get away for the evening? Then this Valentine’s Day, enjoy a staycation at the beautiful Le Meridien Chicago – Oakbrook Center. The Valentine’s Day Romance Package, starting at $199, you will enjoy breakfast in bed, or breakfast at the 9th floor restaurant, El Tapeo, for tapas and views. Don’t believe us? Check out our staycation review and For more details on the romance deal, click here.

Dinner & Drinks

Dinner for Two at Chez Moi
One of our favorite French restaurants, Chez Moi, is offering a special menu to help lovers dine to their heart’s content this holiday. With a menu featuring escargot, mushroom ravioli, and macaron brochette, you won’t find a more delicious way to wine and dine your love. The menu won’t last long, February 10th through February 14th, so grab your reservations before they fill up. For more information, click here.

Estelle’s “Wine About Your Love Life” evening
With half-priced glasses of wine at Estelle’s on Valentine’s Day, it certainly leaves little to whine about. Come join this Bucktown favorite with your girlfriends, or S.O. and enjoy food, drinks, and delicious wine. For more information, click here.

Dive Bar
Dive Bar makes dining on oysters easy with the $1 oyster special this Tuesday! Dive into the newly re-concepted menu this Valentine’s Day. Reservations are recommended and for more information, click here.

Easy Bar
Looking for some a bit more casual? Then head to Easy Bar with its $2 and $3 select beers from 5 p.m. until 7 p.m. There’s nothing like a cheap date night to help you get through all the hearts and cupids. For more information, click here.

Whiskey Business
One of our favorite Wicker Park hotspots has upped the ante: dinner and a movie this February 14th! For $95, you and your date can choose an appetizer, one entree per person, and dessert whilst watching two classic romance movies. The Notebook will be screened at 6:30 p.m. and Grease will be screened at 9:00 p.m. To RSVP, email:

Brunch for Valentine’s Day weekend

Kanela has never disappointed us for brunch, and these special items for Valentine’s Day only up the ante. And the best part, is Kanela is going to serve this special menu all week long. For more information, click here. To read our latest review of Kanela, click here, and for more details on the Valentine’s Day specials, click here.

Bloody Mary bar + chocolate fountain + a kissing booth = a love birds paradise at Carnivale for Valentine’s Day weekend brunch. We loved the brunch at Carnivale, and certainly recommend this unique and lively spot. Read our review here, and for more information, click here.

Shaw’s Crab House
A seafood lovers delight is what Shaw’s is promising to offer at this delicious Valentine’s Day buffet. Better yet, diners will be treated with a $55 gift certificate for future use upon dining there for brunch. Read our review here and for more information and reservations, please call: (312) 527-2722.

Troquet River North
Nothing like a delicious, three course prix fixe menu to start your Valentine’s Day weekend off right! The special menu will be available for $35, and with options like buckwheat crepes, slow roasted prime sirloin, and scallops on the menu, how can you resist? For more information, click here!

Things To Do

Cupid’s Undie Run
For those of you who love to give back, and stay fit, then join in on the Cupid’s Undie Run. Runners raise money for Children’s Tumor Foundation, and while this race might be in your underwear, just know it’s for a good cause! For more information, and tickets, click here!

Cupid Has A Heart On
Chicago’s longest running musical sketch comedy show is back starting Saturday February 11th through the 14th. This sketch comedy is perfect for friends, singles, and couples alike and will certainly be full of feisty songs that everyone can relate to. For more information, click here.

#DateMe: An OKCupid Experiment
Second City: where the careers of many of the funniest actors and writers in prime time began. And the reopening by popular demand of #DateMe: An OKCupid Experiment has certainly brought tears of laughter to many partons eyes. Tickets are still available, and this is certainly a show not to be missed. For more information, click here.

BYOB Painting Class
If you’re looking for a fun, crafty outing with your sweetheart, then try this BYOB Valentine’s Day couple painting class. For $40 per person, you will be supplied with all the materials to paint a beautiful picture worth hanging in your home. For more information, click here.

House of Blues John Vincent’s Sinatra Valentine’s Day Show
The House of Blues is bringing more musical magic with John Vincent’s Sinatra Valentine’s Day show! We loved the show the house of blues brought for brunch, so we can only imagine what John Vincent will bring. For more information, and tickets, click here.

Pajama Crawl
What would make a bar crawl with a breakfast buffet, giveaways, and gift cards? Being able to wear your pajamas, right!? Well, the Pajama Crawl that is happening this weekend is exactly that. Grab your friends, and your favorite onesie, and peruse Wrigleyville the most comfortable way possible. For more information, click here.


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