Welcome to the Windy City, where the vibrant pulse of Chicago comes alive with endless possibilities for an unforgettable weekend! Whether you’re a local seeking new adventures or a visitor eager to dive into the heart of the Midwest, our curated list of the Best Things To Do in Chicago This Weekend is your passport to a whirlwind of excitement. From iconic landmarks to hidden gems, cultural delights to culinary wonders, this weekend in Chicago ensures an immersive experience that caters to every taste and preference. Get ready to explore, indulge, and make memories in a city that never fails to captivate. The only question is, where will your Chicago adventure begin?
Here Are The Best Things To Do In Chicago This Weekend: Jan 05–07, 2023
1) 37th Annual Young Playwrights Festival
Discover the magic of young talent and creativity at the 37th Young Playwrights Festival in Chicago. This festival showcases the captivating stories of emerging playwrights, offering a diverse range of narratives from dramas to comedies. Immerse yourself in the future of performing arts and enjoy an evening of inspiration, entertainment, and unbridled creativity.
When:- Thu Jan 04 2024 at 07:00 pm to Sun Jan 28 2024 (GMT-06:00)
Where:- Pegasus at Chicago Dramatists, 798 N. Aberdeen, 798 N Aberdeen St, Chicago, IL 60642, United States
2) Peep Show Chicago’s Finest Burlesque
Prepare for a night of glamour, allure, and unbridled entertainment as Peep Show: Chicago’s Finest Burlesque Show takes center stage in the heart of the city. This electrifying night invites you to experience the art of burlesque in its most captivating form, showcasing the talent and allure of Chicago’s finest performers.
When:- Sat Jan 06 2024 at 10:00 pm to 11:30 pm (GMT-06:00)
Where:- Storyville Chicago, 712 North Clark Street, Chicago, United States
3) Bowie Bowl Concert
Immerse yourself in a musical journey celebrating the iconic David Bowie at the Bowie Bowl Concert in Chicago. This unique night pays homage to the legendary artist, ensuring an unforgettable experience for Bowie enthusiasts and music lovers alike. You may enjoy an evening filled with stellar performances, tribute acts, and a celebration of Bowie’s timeless contributions to the world of music.
When:- Sat Jan 06 2024 at 09:00 pm
Where:- Metro Chicago, 3730 N Clark St, Chicago, IL 60613, United States
4) 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
5) Salsa Bachata Dance Lessons Chicago
Get ready to groove and twirl at the Salsa & Bachata Dance Lessons which ensures to be fun even if you are a dance enthusiast or a beginner. It offers a welcoming space to learn the vibrant moves of salsa and bachata. There will be experienced instructors, the lessons which ensures a lively and cultural dance experience suitable for all skill levels.
When:- Choose your preferred slot accordingly!
Where:- Dennis PaSamba Dance Company | Chicago, 4429 N Milwaukee Ave, Chicago, IL 60630, USA
6) Rudolph’s Rooftop at LondonHouse Chicago
Elevate your holiday spirit at Rudolph’s Rooftop, set atop the iconic LondonHouse Chicago. This enchanting night offers a winter wonderland atmosphere with festive decor and stunning city views. You may indulge in holiday-inspired culinary delights, enjoy live entertainment, and cozy up by fire pit lounges, and sip on seasonal cocktails while celebrating the magic of the season with friends and loved ones.
When:- Sat Nov 18 2023 at 08:00 pm to Sun Jan 28 2024 at 12:00 am (GMT-06:00)
Where:- LondonHouse, 85 East Wacker Drive At North Michigan Avenue, Chicago, IL 60601, United States
7) YAM Winter Party
Young Adults 18–35 are invited to the biggest holiday social gathering of the year to start your year off right at the annual YAM Winter Party! This is going to be the biggest social gathering of the year: games, prizes, karaoke, vision board station great food & more, So what are you waiting for?!
When:- Fri Jan 05 2024 at 06:30 pm to 09:00 pm (GMT-06:00)
Where:- Apostolic Church of God, 6320 South Dorchester Avenue, Chicago, United States
8) Dia de los Reyes Holiday Scholarship Fundraiser
Participate in the joyous annual Día de los Reyes Holiday Scholarship Fundraiser in Chicago, where cultural celebrations merge with a noble cause. This fundraiser combines festive traditions with a scholarship fundraiser, offering you a chance to enjoy cultural performances, delectable treats, and meaningful contributions.
When:- Fri Jan 05 2024 at 05:30 pm to 08:30 pm (GMT-06:00)
Where:- La Villa Restaurant Lounge and Banquets, 3638 N Pulaski Rd, Chicago, IL 60641, United States
9) Shakespeare’s Measure for Measure
Experience the timeless brilliance of Shakespeare’s Measure for Measure in Chicago, where the classic play comes to life in a captivating performance. You may delve into the intricate web of love, power, and morality as talented actors breathe new life into this Shakespearean masterpiece. It will be a night of drama, eloquence, and the enduring magic of Shakespeare’s storytelling.
When:- Choose your preferred slots accordingly!
Where:- The Raven Room, 4702 N Ravenswood Ave Suite B, Chicago, IL 60640, United States
10) National Veterans Art Museum Tour
Embark on a unique journey through the powerful narratives of the nation’s heroes at the National Veterans Art Museum. Chicago Veterans cordially invites you to a private tour of the National Veterans Art Museum on January 6th, 2023, and immerse yourself in the rich tapestry of the nation’s military history through a remarkable collection of art.
When:- Sat Jan 06 2024 at 11:00 am to 12:30 pm (GMT-06:00)
Where:- National Veterans Art Museum, 4041 North Milwaukee Avenue, Chicago, United States
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