Event Dates
From: Friday, November 17, 2023
To: Monday, January 1, 2024
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
- November 17 – December 24 – 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
- Typically from mid November – 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, November 18th, 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
- Early December, 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 – Unplugged
- Awaiting dates – Celebrate the holiday spirit with Chicago’s most colorful chorus! Join CGMC as we ring in the festivities with A cappella favorites.
- Strip away all the extra tinsel to reveal the true musical meaning. Featuring acoustic versions of grand hits and unplugged disco favorites, this year’s holiday show will get you in the mood to plug in your holiday decorations!
Christmas Light Experiences
- From early November – 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.
- From mid November – ZooLights at Lincoln Park Zoo: This over-the-top light display, which includes more than one million twinkling bulbs, is a beloved local tradition.
- From mid November – 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 mid November – 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.
Light Up the Lake at Navy Pier
- From late November – 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.
Book with confidence. Get the best Prices from our partner Booking.com
We have chosen hotels in Chicago that keep you close to all the shops, restaurants & bars
Located along the Magnificent Mile, this Chicago hotel is 5 minutes’ walk from the Museum of Contemporary Art. The hotel offers a full-service Asian-inspired spa, award-winning restaurants, and spacious luxury guest rooms with city views. A 42-inch flat-screen TV and free WiFi
Located in the centre of the Loop, near Chicago’s theater and financial district, this hotel is close to dining, shopping, and many major attractions. Spacious rooms include cable TV and free WiFi. Featuring a contemporary design, each room includes a refrigerator and coffeemaker
Every room at Kimpton Gray Hotel includes a flat-screen TV, iPod docking station & a private bathroom with bathrobes and luxury Atelier Bloem bath products. Select rooms offer a separate living room & spa bath. Boleo offers breathtaking rooftop views alongside Latin-inspired cocktails & cuisine.
Located in the Chicago city centre, this luxury boutique hotel boasts an on-site restaurant and WiFi access. Shopping and dining on Michigan Avenue is 2 minutes’ walk away. A flat-screen cable TV and a mini bar are offered in every modern guest room
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.