10 Cutest Winter Date Ideas in Chicago

There's something magical about a winter date night in Chicago!

November 26, 2018

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Beat the winter blues this season by going on some dates with your significant other. 

There are so many adorable places in Chicago for a cute date night that also takes advantage of the colder weather.

There's something magical about winter date nights -- they feel cozier, time goes by slower and there's no excuse for not cuddling. 

Have a date night idea you want to add? Let us know! 



1. Explore Christkindlmarkt 

This one is a given. There's nothing more romantic than spiced, warm Gluhwein, German pretzels, bratwurst, and browsing intricate holiday ornaments and shops.

Nothing beats Christmas time in Chicago ✨-- . . . . . #christmas #chicago #christmasinchicago #christmasmarket #germanchristmasmarket #christkindlmarkt #christkindlmarktchicago #winter #festive #tistheseason

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2. Ice Skate at Millennium Park

Holding hands while skating around and taking in the skyline views? Sounds like something straight out of a Hallmark holiday movie! It's a must-do during winters in Chicago.

There are so many fun things to do in Chicago during the Holidays. You can go skating at the McCormick Tribune Skating Rink at Millennium Park.

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3. Embrace Christmas at Frosty's

If you're looking for a place with Christmas spirit, it's here. It looks like Christmas threw up at Frosty's Pop-Up Bar which makes it the happiest place on Earth for Christmas-lovers.  

It’s beginning to look a lot like Christmas -- at Frosty’s Christmas Bar -- Opening November 21st. Get your tickets -- today @ WeLoveFrostys.com Even the naughty deserve something nice! #frostyspopupbar #chicagopopup #christmasbar #christmasinchicago #christmasdecor #chicagodrinks #chicagoland #friendsgiving #friendsmas #uglysweater #bestpopupbarinchicago #bestpopupbarchicago #jackspumpkinnights #jackspumpkinpopup #frostys #frostyschristmasbar #chicagopopup

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4. Take in the Zoo Lights 

Take your date to the Lincoln Park Zoo to check out 3D displays, ice sculptures, and a musical holiday light show.  for an outstanding light display on select dates in November and December, ending January 1.

Zoo Lights! #chicago #zoolights #lincolnparkzoo #lincolnparkzoolights #brightlightsbigcity #chicagoatnight #christmasinthecity #christmasinchicago

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5. Sip Hot Cocoa at Mindy's Hot Chocolate 

Hot cocoa is the only pairing for winter in Chicago. Mindy's Hot Chocolate is famous for its hot chocolate, go figure. Choose from several varieties including peppermint and Mexican. Trust us, this is the only way to survive winter. 

#mindyshotchocolate #mindyshotchocolatechicago #hotchocolate #giantmarshmallows #cousindate #girlsday #familytime #cousincatchup #brunchwithfamily #brunchatmindys #sundaybrunch

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6. Cozy Up by the Fire at Park & Field

The vintage-style sports bar has some of the best comfort food in town (mac and cheese is my personal fave) along with hot drinks that will warm you right up (Apple Cider with Jack Daniels) and an outdoor patio with a big fire pit to keep you nice and toasty! They also offer a wide variety of board games to entertain you and your significant other! 

#Repost @larissa.m.thomas : Haven’t seen a cuter scene yet; haven’t read a cuter caption ever. Hope the date night was as on-point as this capture ・・・ Festive little date night with @chris.c.thomas -- How cute is @parkandfield ?!

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7. Grab a Sizzlin' Bowl of Chili at Heaven on Seven

Southern-inspired restaurant Heaven on Seven is charming, extremely cozy and serves up sizzlin' beef that will take you from Chicago to Louisiana! Other favorites from the Cajun and Creole kitchen include the gumbo and jambalaya!

Fried Oyster Plate : Southern Style #friedoysters #southernstyle #food #lunch #meal #heavenonseven #heavenonsevenwabash #hotsauce

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8. Shop and Take in the Views at Roosevelt Collection

Get a little Christmas shopping done with a collection of Chicago's favorite stores, then catch a movie and finally, snap the perfect Instagram-worthy winter shots at Roosevelt Collection. In addition to brand-new winter decor, including a larger-than-life Christmas tree and intricate holiday lighting, there is nothing better than snapping a shot of the snow falling over the skyline!

Never too cold for these views. ----

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9. Go Sledding

Chicago isn't known for its hills — we're the second flattest state in the US — however, there are some spots that you can utilize for sledding after it snows! Cricket Hill just west of Montrose Harbor is one of the perfect spots for sledding and tubing! Check out more options right here!  

Sliding into the new work week like... . . . #AirheadSportsGroup #WinterIsComing #Sledding #SnowTubing #outdoorfamilies #childhoodunplugged #raiseawildchild #adventurekids #littleandbrave #weareoutdoor #outdoorist #getoutstayout #getoutandplay #optoutside #GoOutside #OutsiderCulture #MakeMoments #FindItLiveIt #LiveAuthentic #lifeofadventure

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10. Take a Cooking Class 

There's nothing more intimate than cooking and frankly, no better time to learn how to cook than when you're cooped up inside. The Social Table has a variety of classes to choose from including Holiday Brunch, Paris Bistro, and Winter Italian. You can show off your cooking chops and impress each other with your culinary skills. Classes also come with a mimosa per person! 

Disproving the old "too many cooks" saying every night of the week! #themorethemerrier #tstchicago #cookingclass #bestdinnerparty

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