Welcome, Windy City enthusiasts! Brace yourselves for an exhilarating journey through the vibrant heart of the Midwest because we’ve got the ultimate guide to make your weekend in Chicago nothing short of extraordinary. From the pulsating energy of the city’s iconic landmarks to the hidden gems tucked away in its diverse neighborhoods, this weekend promises to be a thrilling escapade for locals and visitors alike. Get ready to uncover a tapestry of experiences, from cultural delights to gastronomic adventures, as we present the Best Things To Do In Chicago This Weekend. Chicago’s calling and the weekend wonders are waiting to be explored!
Check Out Things To Do In Chicago This Weekend: Dec 09–10, 2023
1) The Trashy Holiday Market
Explore unconventional holiday festivities at The Trashy Holiday Market in Chicago! From unique shopping and DIY trashy crafts to an Ugly Sweater Contest and live performances, this event offers a quirky twist on the traditional holiday scene. Enjoy trashy treats, participate in a Trash to Treasure exchange, and join interactive workshops. Also try to attend the Trashy Fashion Show and scavenger hunt.
When:- Sun Dec 10 2023 at 01:00 pm to 05:00 pm (GMT-06:00)
Where:- Ignite Glass Studios, 401 N. Armour Street, Chicago, United States
2) Brunch with Santa and Ornament Painting
Experience a merry morning at Brunch with Santa & Ornament Painting on this weekend. Also, enjoy a delicious brunch, engage in ornament painting for all ages, and meet Santa for festive photo opportunities. Immerse yourself in the holiday spirit with decorations and a cheerful ambiance. This special brunch is arranged for a joyous celebration with family and friends!
When:- Sun Dec 10 2023 at 11:00 am to 02:00 pm (GMT-06:00)
Where:- The Old Plank, 2700 North Milwaukee Avenue , Chicago, United States
3) Disney100: The Exhibition Chicago
Embark on a magical journey through the enchanting world of Disney at Disney: 100 Years of Magic — The Exhibition in Chicago! Celebrating a century of storytelling, creativity, and pure imagination, this immersive exhibition is a must-visit for Disney enthusiasts of all ages. Whether you’re a fan of Mickey Mouse, a devotee of Disney princesses, or captivated by the magic of Pixar, this exhibition ensures a journey through the heart and soul of a century of Disney enchantment.
When:- Sat Nov 18 2023 at 09:00 am to Sun Dec 31 2023 at 07:00 pm (GMT-06:00)
Where:- EXHIBITION HUB ART CENTER, 2367 W Logan Blvd, Chicago, Illinois 60647, United States
4) Holiday River Cruise & Fireworks Party
Sail into festive bliss at Chicago’s 21+ Holiday River Cruise and Fireworks Party. Enjoy a scenic river cruise with breathtaking views of the city’s festive lights and a spectacular fireworks display. Revel in the holiday spirit with live music, DJ sets, and lively entertainment while raising a toast with seasonal cocktails.
When:- Sat Dec 09 2023 at 06:30 pm to 09:15 pm (GMT-06:00)
Where:- 200 N Breakwater Access, 200 North Breakwater Access, Chicago, United States
5) Chicago’s Finest Burlesque Show — Peep Show
Step into a world of glamour and allure at Peep Show: Chicago’s Finest Burlesque Show. This night promises sizzling burlesque acts, various performances, and a sultry atmosphere blending tradition with modernity. Enjoy craft cocktails and libations as you immerse yourself in the captivating world of burlesque.
When:- Sat Dec 09 2023 at 11:30 pm to Sun Dec 10 2023 at 01:00 am (GMT-06:00)
Where:- Storyville Chicago, 712 North Clark Street, Chicago, United States
Hey there, readers! Are you looking for an exciting weekend?
No Fear, When Events Guide is here! As we have announced earlier, we will bring your holiday treats whenever you come up looking for them. This time, we have a lot of fun, laughter, and a giant parcel of enjoyment.
The city boasts a diverse array of comedy shows that cater to every comedic taste imaginable. Here, we have curated a list of laughter-filled Comedy Shows in Chicago:
Get ready for a night of laughter at the Chicago Comedy Club at the House of Blues. This comedy extravaganza features a diverse lineup of stand-up comedians showcasing their unique styles and humorous anecdotes. Set in the vibrant atmosphere of the House of Blues, the event promises a lively and entertaining experience. Enjoy drinks and bites while reveling in the comedic brilliance on stage.
Experience the ultimate holiday drag extravaganza at The Jinkx and DeLa Holiday Show in Chicago. Join drag royalty Jinkx Monsoon and BenDeLaCreme for a festive spectacle featuring live singing, comedy, and interactive audience engagement. The show blends glamour, humor, and holiday spirit, creating an unforgettable experience.
6) 5th Annual UGLY Sweater Party and Toy Drive
Join the festive fun at the 5th Annual Ugly Sweater Party and Toy Drive in Chicago! Bring an unwrapped toy for the charitable initiative, participate in the Ugly Sweater Contest, and dance to festive beats. Enjoy specially crafted holiday drinks and make this event a heartwarming celebration of generosity and joy.
When:- Sat Dec 09 2023 at 09:00 pm to Sun Dec 10 2023 at 01:00 am (GMT-06:00)
Where:- Bourbon on Division, 2050 West Division Street, Chicago, United States
7) Chicago’s 27th Annual Xmas Crawl
Unwrap the festive fun at TBOX, Chicago’s 27th Annual Xmas Crawl. Join a spirited pub crawl through iconic neighborhoods adorned with holiday cheer. Don your best holiday attire for a costume contest, enjoy live entertainment, and savor special holiday drinks. Receive a Santa’s goodie bag filled with treats. Don’t miss this unforgettable Christmas celebration that promises to be the highlight of the holiday season in Chicago!
When:- Sat Dec 09 2023 at 09:00 am to 07:00 pm (GMT-06:00)
Where:- 3506 N Clark St, Chicago, IL 60657–1612, United States
8) McCormick Tribune Ice Rink 2023–24
Experience the winter enchantment at the McCormick Tribune Ice Rink 2023–24 in Millennium Park, Chicago. The family-friendly event offers seasonal music, a Winter Village with treats, and winter workshops for all skill levels. Immerse yourself in the holiday spirit with twinkling lights and festive decorations. So, Glide into the magic of winter at this iconic Chicago attraction!
When:- Thu Dec 07 2023 at 11:00 am to Sat Feb 03 2024 at 10:30 pm (GMT-06:00)
Where:- Millennium Park, Chicago, IL, United States
9) Decemberg Winter in the Woods 2023
Prepare to be enchanted by the Decemberg Winter in the Woods 2023, a magical celebration nestled in the heart of Chicago. Immerse yourself in a transformed woodland setting with sparkling lights, live performances, and festive music. Explore a holiday market for unique gifts, enjoy skating, and meet Santa Claus. This family-friendly event promises a joyous atmosphere and holiday cheer.
When:- Sat Dec 09 2023 at 07:30 am to Sun Dec 10 2023 at 04:00 pm (GMT-06:00)
Where:- Roscoe Village Bikes, 2016 W Roscoe St, Chicago, United States
10) Chicago’s 110th Annual Christmas Tree Lighting
Get ready to kick off the festive season in grand style as the city of Chicago invites you to witness the magic of its 110th Annual Christmas Tree Lighting! There will be a night filled with Santa’s grand arrival, a musical extravaganza, a dazzling lights display, a holiday market, delicious food, and plenty of photo opportunities. Embrace the spirit of giving through charitable activities. This iconic event promises to usher in the holiday season with joy and enchantment.
When:- Thu Nov 17 2023 at 06:00 pm to Sun Jan 07 2024 at 11:00 pm (GMT-06:00)
Where:- Millennium Park, Chicago, IL, United States
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