Even this fall-themed cafe is getting in the holiday spirit 🎄✨ Head to October Cafe in Norwood Park to try their coffee Holiday Flight + meet Santa Claus + The Grinch throughout the season 🎅 #chicago #chicagobucketlist

Obsessed with this hot cocoa at Little Goat Diner ☕🤩 Who wants to try? #chicago #chicagobucketlist

Son of a nutcracker 😂 Who else has seen Buddy the Elf around Wrigleyville?🎄 (🎥: getdownlo__ via TT) #chicago #ChicagoBucketList

The Christkindlmarket Chicago is now open 🎉 This year they have two locations: 📍 Christkindlmarket Chicago at Daley Plaza : Open daily! 📍 Christkindlmarket Aurora at RiverEdge Park : Open Thursday through Sunday. who do you want to go with? 🎄❤️ #chicago #chicagobucketlist

Need to get these in our hands asap 🥐☕️ Find this giant croissant and hot chocolate at Sugary Chicago ! Perfect to share with friends on the next outing 🥰 #chicago #chicagobucketlist #winter

Have you seen the holiday train yet? 🎄🚊 See the schedule below, and make sure to keep an eye out for special Santa sighting opportunities! 💓Pink Line: 12/10–12/11 & 12/14 (photos with Santa offered 12/14) ❄️Blue Line: 12/12–12/14 (photos with Santa offered 12/14) 🌹Red Line: 12/17, 12/19 &

Last week’s holiday drone show at Navy Pier ! 🙌🎡 Did you see it? Pro-tip: the next drone show will be next Friday on 12/13 starting at 9pm! (🎥: sheyhernandez96 via TT) #chicago #ChicagoBucketList

It’s that time of year to remind you that the Home Alone house is only a 45-minute drive from Chicago 😱🏠 Which filming sites have you been to? (🎥: kellykurowski via TT) #chicago #chicagobucketlist #homealone

It’s hot chocolate season 🤤☕ Enjoy a chocolatey, thick drink topped with homemade marshmallows at Katherine Anne Confections (🎥: liv.your.best via TT) #chicago #chicagobucketlist #winter

When your brunch spot feels like a scene out of a storybook ✨🌿 3 Arts Club Cafe at RH Chicago brings magic to life in Chicago’s Gold Coast neighborhood #chicago #chicagobucketlist

Two icons that got their start in Chicago 🍬✨ The malt shake was invented by Ivar “Pop” Coulson in 1922, and Margie's Candies has been serving delicious treats since 1921. We recommend their Fudge Royal Malt! #chicago #chicagobucketlist

Back for the holiday season! 🎆 Check out Navy Pier ’s weekly firework shows every Saturday starting November 30 thru December 21 at 9pm! Pro-tip: There will also be holiday drone shows on December 6 & 13 at 9pm as well as a NYE fireworks show at midnight on December 31! Tag someone who needs t

Holiday gift idea 💡🎁 We found the viral jellycat plushies at Uncharted in Oak Brook! Share with someone who needs to know! (🎥: amanduhhhh via TT) #chicago #chicagobucketlist #holiday #GiftIdeas #jellycat

Get your winter wardrobe ready at these vintage shop gems in the city ❄️ 1. Vintage Frills 2. Lost Girls Vintage 3. Gem: A Vintage Collective Which one are you going to? 🛍️ #chicago #chicagobucketlist #shopping

Live views from Maggie Daley Park ❄️☃️ We’re expecting 1-3 inches of snow! Who’s excited? - 🎥: king_gupta via IG #chicago #chicagobucketlist #winter

Tag your fellow Hello Kitty lovers 😍 Enjoy tasty food + choose your flavor and cup color to take home at Tacotlan ! #Chicago #chicagobucketlist

This year’s CTA holiday trains are expected to return the Friday after Thanksgiving on November 29 through December 23 🚋🎄The unique tradition began over 30 years ago when a “Season’s Greetings from the CTA” sign was placed on the front of an out-of-service train used to deliver food to various cha

Cute Gem in Wicker Park 💌🎨 Find it at the corner of Pierce Ave + Leavitt St #chicago #chicagobucketlist

Weekend trip idea from Chicago ✨ Pro-tip: Frankenmuth is only 5 hours from Chicago and 1.5 from Detroit ! Tag your road trip buddies (🎥: alabamasavannah via TikTok) #chicago #chicagobucketlist #roadtrip