Event Dates
From: Friday, November 21, 2025
To: Sunday, January 4, 2026
Chicago is a magical city during the Holiday Season. Explore traditional German-style Christmas Markets, take in a festive parade.
Chicago is a magical city during the Holiday Season. Explore traditional German-style Christmas Markets, take in a festive parade, visit Boystown for some festive fun nights out and shop till you drop on the Magnificent Mile. Here’s our shortlist on what to see and do this holiday season.
- Stay close at the Hotel Zachary for the perfect gay Christmas escape. The 4-star hotel has chic rooms with excellent amenities and a delicious onsite bakery. It is also close to the markets and the city’s busy gay district.
Christkindlmarket
- Next Edition: Friday 21st November 2025 – Wednesday 24th December 2025
- Christkindlmarket is a Christmas market held annually at Daley Plaza. The festival attracts more than 1 million visitors each year.
- The smell of roasted nuts, fresh pretzels, bratwurst and hot spiced wine, the sound of festive music, and the glimmer of sparkling Christmas ornaments, all in a cosy atmosphere – a visit to the market, takes all your senses on a journey!
- Open Sunday – Thursday: 11 am – 8 pm, Friday – Saturday: 11 am – 10 pm
- Stay at the Cambria Hotel Chicago Loop – Theatre District , rated “fabulous” with spacious rooms located on the steps of the plaza, the perfect location to take in the markets.
Winterland at Gallagher Way
- Sunday 23rd November 2025 – Wednesday 31st December, 2025 – Go ice skating, take curling lessons, enjoy a Hanukkah celebration, and shop at the holiday market at this winter wonderland.
- This market is close to all the gay bars in Lakeview.
Magnificent Mile Lights Festival
- From Saturday 22nd November, 2025 – Festivities begin at 11:00 am, starting in Lights Festival Lane (401 North Michigan Avenue) with a festive thoroughfare of booths and family activities until 4:00 pm ending with the grand tree-lighting parade down North Michigan Avenue at 5:30 pm.
- The parade features more than 60 minutes of fabulous floats, giant helium balloons, exciting marching bands, celebrities, musical performances, Santa Claus, and more, all helping to illuminate more than 1 million lights along The Magnificent Mile. The event draws to a grand conclusion with spectacular fireworks over the Chicago River at the DuSable Bridge at 7:00 pm (9 mins drive from the gay district, Boystown)
- Enjoy the lights of the Magnificent Mile throughout the holiday season. The Magnificent Mile is Chicago’s premier commercial district, perfect for all your Christmas gifts. The vibrant, bustling area is home to upscale shops, luxe fashion outlets, fabulous restaurants and the city’s top hotels.
Chicago Speedo Run, Northalsted
- Saturday 6th December, 2025, Runners strip down to their skivvies for this annual holiday charity run (link to our page event you just created – dont have the link ), during which scantily-clad participants traverse a 1-mile stretch of the city’s downtown.
Chicago Gay men’s Choir – Holy Dolly Christmas
- Friday 5th December, 2025 Celebrate the holiday spirit with Chicago’s most colorful chorus! Join CGMC as we ring in the festivities with A cappella favorites.
- Celebrate the holiday season in neon colours, boomboxes and big hair! Songs from this decade are sure to get you in the festive spirit.
Christmas Light Experiences
- November 14th 2025 – January 4th 2026 – Lightscape at Chicago Botanic Garden: – Be awed by this magical outdoor light show that takes over these sprawling Glencoe gardens. Hum along to the melodic tunes of the singing trees. Surround yourself in the twinkling glow of the Winter Cathedral, and find new features that shine with all the colours imaginable. This holiday season set a merry mood with friends and family.
- November 21st, 2025–January 4th, 2026 – ZooLights at Lincoln Park Zoo: This over-the-top light display, which includes more than one million twinkling bulbs, is a beloved local tradition.
- November 15th 2025 – January 3rd 2026 – Illumination: Tree Lights at The Morton Arboretum: – Each winter, the trees at this Lisle nature attraction come to life with festive lights and music. Explore 50 acres of the Arboretum’s majestic trees during this one-of-a-kind spectacle of colour, light, and sound.
Christmas Tree & Ice skating in Millennium Park
- From November 21st 2025 – Capture that Instagram moment at the Chicago Christmas Tree in Millennium Park.
- Grab your skates and check out the two scenic and free ice rinks that pop up in the park each winter.
- The Holiday Market is a popular destination that draws thousands of visitors eager to start their holiday shopping. Sponsor activations will be set up alongside dozens of Chicago-area artists selling jewelry, pottery, artwork and more, as well as amazing holiday gifts. The 3-day market runs through the weekend, scheduled for November 21st to 23rd 2025.
- Holiday Sing-Along – local Chicago choral groups lead hundreds of celebrants in song in front of Cloud Gate (“The Bean”). These festive gatherings are part concert, part sing-along and super fun. Scheduled on Fridays December 5, 12 and 19.
Winter Wonder Fest at Navy Pier
- From December 5th, 2025, to January 4th, 2026 – Light sculptures, a skating rink, holiday beer garden and more take over Navy Pier for the holidays all season long. The indoor, temperature-controlled experience features a sprawling light garden of large-scale sculptures comprising more than 600,000 twinkling lights. Take a ride on the iconic Centennial Wheel, offering inspiring views of the city all decked out for the holidays. (10 mins drive from the gay district, Boystown)
- For a unique Christmas experience close to the Magnificent Mile and Navy Pier, stay at The Langham Chicago offering fantastic views of the city. The hotel has a superb indoor pool, a great gym, and just steps from Chicago’s Christmas festivities.
New Year Fireworks at Navy Pier
- December 31st – Ring in the New Year with a breathtaking firework display over Lake Michigan at Navy Pier.
- The fireworks are set to music, and the event attracts thousands of visitors.
Gay New Year Parties
- Hydrate hosts an annual NYE countdown, one of the most popular in the city.
- Start your night out in Sidetrack, one of the most popular bars in the gay village.
- Organised Grime host the CunTea and LOAD parties during the festive season.
- Luxuria, a pop-up party promoter also hosts several parites during Christmas.
Recommended Hotels
Here are the hotels we recommend that have good reviews and keep you close to all the action,
get an early deal on your hotel
Book now and pay on arrival.
The Hyatt Regency is close to all the main
events & offers superior rooms & service.
For further information and advice on
Christmas in Chicago visit The Website
The area in Chicago with the most gay bars is Boys town offering over 20 bar, we have chosen hotels close to this area that have good revues on bookings.
Address: 108 E Superior St, Chicago, IL 60611
Address: 21 E Bellevue Pl, Chicago,
Address:
Address: 10 S Wabash Ave, Chicago,
Address: 933 West Belmont Avenue Chicago
Address: 3434 North Broadway Chicago
Address: 528 West Brompton Avenue Chicago
Address: 3439 North Halsted Street Chicago
Address: 3359 North Halsted Street Chicago
Address: 3452 North Halsted Street Chicago
Address: 3729 North Halsted Street Chicago
Address: 3325 North Broadway Street Chicago
Address:
Address:
Address: 3320 North Halsted Street Chicago
Address: 3339 N Halsted St, Chicago
Address:
Address: 3702 North Halsted Street Chicago
Address: 3458 North Halsted Street Chicago
Address: 3356 North Halsted Street Chicago
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We have chosen hotels in Chicago that keep you close to all the shops, restaurants & bars
Chicago’s favorite winter wonderland, Christkindlmarket.
Chicago, affectionately known as the “Windy City,” is a must-visit destination for LGBTQ+ travellers seeking a vibrant, welcoming, and diverse experience. The city is home to Northalsted (formerly Boystown), one of the first officially recognized gay villages in the United States. Remember, Chicago has an efficient public transit system, so you’ll have easy access to all the city offers no matter where you stay.
The heart of Chicago’s downtown and home to some of its most iconic landmarks with great hotels.
A great place to stay if you’re a foodie or a fan of the arts, and close to the city’s best shopping.

London Christmas Markets Lights & Attractions