Ice skating at The Peninsula Chicago’s Sky Rink or embarking on an epic holiday food crawl? Don’t mind if we do.

Yes , Chicago is inhuman in the wintertime . But it ’s also pretty darn magical . Along with the icy temporary , the Windy City unveil its magical side during the winter holiday season . As Chicago bundles up with the seasonal charm , we ’re here to channelise you through its greatest hits , from classic to freshman . Deck the halls , grab a fond chapeau , and keep register for how to drench up the most wonderful time of the year in Chicago .

Eat, drink, and be merry on aholiday food tour with Bobby’s Bike Hike.

guide tour companyBobby ’s Bike Hikeis here to guarantee you and your crew leave Chi - town with every holiday solid food phantasy accomplish . During the three - hourHoliday Hike – Festive Food & Walking Tour of Downtown Chicagotour , you ’ll experience some of Chicago ’s tastiest seasonal treats . The tour departs at 11:30 am daily from Lou Malnati ’s Pizzeria in the Wrigley Building , and has you wind your way of life through business district Chicago for about 1.25 mile as you visit one of Chicago ’s German Christkindlmarkets , Millennium Park ’s Christmas Tree , the Magnificent Mile , the Macy ’s vacation window displays , and more . Along the way , you ’ll nosh on Chicago ’s famous rich - dish pizza , a traditional Chicago - style hot dog , and the Chicago pixy , invented at the Palmer House hotel . Tickets be $ 70 per person and include all food sample ; an extra $ 20 gets the 21 - and - up set the prospect to sip on three craft beer samples with their meals . Do n’t forget to tiptoe your tour guidebook ! To save everyone in your group from digging up the correct amount of hard currency , designate one tipper lorry on behalf of your company and give ‘ em back fleetly and safely with Zelle ® .

VisitChristkindlmarket Chicagofor some old-fashioned, European-inspired fun.

Christkindlmarket — a liberal - entrance money event model after Germany ’s sixteenth - hundred holiday markets — has been a holiday custom in the Windy City since 1996 . This yr , the popular Christkindlmarket Chicago has localization in business district Chicago , Wrigleyville , and Aurora . Whether you ’re thirsty , thirsty , or appear for handcrafted gifts ( or all three ) , you ’re sure to find something to become your needs at this fabulous out-of-door bazaar for German grub , warming hot cocoas and mulled wines , and handmade gifts . mention : While admission to the market is free , food , potable and endowment must be purchased ; all three location unfastened on November 17 ; Aurora and Chicago locations close for the season on December 24 , and Wrigleyville on December 31 .

Ring in the most wonderful time of the year at theJack Frost Christmas Holiday Pop-Up.

Here ’s another holiday experience you wo n’t want to miss in Chicago . At Fulton Market from November 25 to January 5 , guests can frolic around two acres of wintertime wonderland with bumper automobile , holiday workshop , an larger-than-life vacation lights display , ice - skating , and Christmas interior decoration aplenty . Come nightfall , adult guest can warm up with boozy hot drinking chocolate as they take the air through the Christmas Sir Herbert Beerbohm Tree timber and knock off some shopping from their holiday gift inclination at the market . ticket start at $ 15 , and you’re able to learn more about radical bookings and partieshere .

See the Joffrey Ballet’sfamed rendition ofThe Nutcracker.

Does it get better than Tchaikovsky music , luxuriant holiday costume , and beautiful ballet dancing ? Throw in the two - time Tony Award - come through choreographer Christopher Wheeldon , and that ’s what you ’ll have atThe Nutcrackerwhen it return to the Lyric Opera House from December 2 through December 27 , 2023 . This rendition of the beloved holiday tarradiddle is set during Chicago ’s World Fair in 1893 , where the young immigrant Marie and her female parent — a sculptor creating the Fair ’s Statue of the Republic — host a Christmas Eve fête . After Marie receives a surprisal visit from the cryptical Great Impresario ( the Maker of the fair ) , she channelize out on an ethereal risky venture with the Nutcracker Prince through a World ’s Fair brim with Yuletide gaiety and Chicago history . The show is accompanied by alive music from the Lyric Opera Orchestra , so expect to be amazed . Tickets start at $ 40 .

Explore the Chicago Botanic Garden’sLightscape.

Running November 10 through January 7 , Lightscape at the Chicago Botanic Garden in Glencoe is quite the gleam production . The after - glum outdoors illuminated track will showcase new installations this season , as well as repay displays such as the Winter Cathedral and a reimagined version of the Fire Garden . Among the novel displays , “ lily ” from UK artist Jigantics is our fave ; it ’s a lovely creation featuring glowing five - infantry lilies float on body of water . Another neophyte is “ Night Lights ” from French creative person TILT , which comprises handsomely designed lamp - form lights that unfold nearly 19 feet in the air . FYI : ticket sell out quickly , so book your clock time and date in progress if you could . advanced ticket for adult ( non - members ) begin at $ 34 and children ( age 3 - 12 ) at $ 19 .

Go ice skating atthe Peninsula Chicago’s Sky Rink.

Hey , even if you ca n’t splurge for a stay at the chichi Peninsula Chicago , you could still frost skate amongst the glitterati . This 2,100 - square - metrical unit ice rink is the only hotel skating rink in Chicago and is currently slat to remain undecided through December 31 . The rink also bump to be perched over Chicago ’s Michigan Avenue , so you could take in adorable views of skyscrapers and sparkling lights as you coast ( and perhaps flop a clock time or two ) . To polish out the experience , hot beverages and collation are usable for purchase at the Chalet and skate are available to rent ( $ 20 for adults , $ 10 for shaver 12 and under ) with 100 % of skate rental proceeds donated to the Ann & Robert H. Lurie Children ’s Hospital of Chicago and Hephzibah Children ’s Association . There are no admission fees beyond the price of skate rentals . The skating rink is typically up and running from 10 am to 8 phase modulation most day , but minute are capable to change so you might desire to call prior to arrival to sustain that your group is good - to - glide .

Hit up the Hanukkah pop-up bar8 Crazy Nights.

Say " l’chaim " at this cozy and welcoming soda pop - up bar ( now in its fifth class ) fete the Judaic festival honoring the recovery of Jerusalem and rededication of the Second Temple there following the Maccabees victory over the tumid Syrian army . put up atThe Graystone Tavernin Wrigleyville , the legal community will be open from November 22 to January 7 . Entry is free , but you ’ll want to order something to exhaust or booze — namely , the laden jalapeño - cheddar latkes , matzo ball soup , or challah grill Malva sylvestris with tomato soup with a tasty cocktail like the Mensch Mule or Aperol Schwitz . There ’s Manischewitz Concord Grape bottle service , too . While you manducate and chug , wanton in the delicious ambiance of blasphemous - and - blanched light and Hanukkah interior decoration or play one of the on - subject board games like Mitzvah Match or Jewish Guess Who ? .

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Eric James Walsh

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Bobby’s Bike Hike, Chicago

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Cheryl Mann

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Chicago Botanic Garden

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The Peninsula Chicago