Your 2025 Chicago Holiday Guide

BEST DATE NEWS

Nov. 20, 2025: Best Date News Volume #153

Welcome to Best Date News, your favorite Chicago weekly newsletter! Thank you for being a weekly reader. With this weekend marking the official kickoff to the holiday season in Chicago, we put together a special holiday edition just for you. We hope you can use this as your go-to guide for what to do in Chicago this holiday season.

Nov. 20: National Holidays

• World Philosophy Day

• National Child’s Day

• National Absurdity Day

• National Peanut Butter Fudge Day

• International Hug a Runner Day

Sponsored by our friends at 8 Hospitality

The Official BAD SANTA Christmas Bar Crawl

• Bad Santa Bar Crawl: A one-day holiday bar crawl is taking over River North in exactly one month. On Saturday, Dec. 20 from 3 p.m. to 9 p.m., West Hubbard Street will turn into a wild Christmas celebration for The Official BAD SANTA Christmas Bar Crawl.

• Grab your crew, suit up in your boldest Santa fits, elf gear or reindeer onesies and get ready to sleigh your way through Chicago’s top bars, including Hubbard Inn, Joy District, Parlay River North, Boss Bar and Point and Feather. Each spot will come alive with themed decor, holiday drinks and plenty of festive chaos.

• Each ticket grants access to the Baddest Crawl of the Year, a custom BAD SANTA mug and Santa hat, no cover at all participating venues, express entry at every stop, exclusive holiday drink specials, festive food deals at select spots, a massive after party to end the night and more.

• Tickets are currently $23.28, their lowest price of the season, but prices will rise soon. Lock in that early bird discount pricing and get yours now.

Chicago Holiday Festivities

• Lights Festival: The Wintrust Magnificent Mile Lights Festival has been arguably Chicago’s most iconic holiday celebration for 33 years, and it’s back this Saturday, Nov. 22! The center of it all is the largest nighttime parade in the United States led by Mickey and Minnie Mouse down North Michigan Avenue. They help kick off the holiday season in Chicago by illuminating one million lights on 200+ trees along the Mag Mile. The event ends with a fireworks spectacular around 7:15 p.m. Get all the details.

• Christmas Tree Lighting: Tomorrow, Friday, Nov. 21, is the 112th Annual City of Chicago Christmas Tree Lighting in Millennium Park. The ceremony will take place near the intersection of Michigan Ave. and Washington St. A pre-show begins at 5 p.m., the official ceremony will kick off at 6 p.m., the tree lighting will be at 6:25 p.m. and fireworks will wrap things up at 6:30 p.m. Here’s what it looks like.

• Christkindlmarket: Celebrate the holidays in Chicago the German way with roasted nuts, fresh pretzels, bratwurst and hot spiced wine at The Christkindlmarket. This year, there will be three locations: two in Chicago at Daley Plaza and Wrigleyville and one in Aurora. Daley Plaza and Aurora open for the season tomorrow, Friday, Nov. 21, while Wrigleyville opens this Sunday, Nov. 23. Admission is free. Check out this year’s mugs.

• CTA Holiday Fleet: One of Chicago’s favorite holiday traditions is the CTA Holiday Fleet, where they deck out the train and bus with dazzling holiday lights! Did you know it’s now their 34th year of operation?! The schedules for the 2025 CTA Holiday Train and the CTA Holiday Bus just went live this week. The Metra holiday train tickets sold out within minutes on Monday.

• Macy’s on State Street: Each year, Macy’s on State Street goes all out for the holidays to become a must-visit destination. They have their iconic holiday window displays, The Marshall Fields Walnut Room with The Great Tree, Santaland, Holiday Shop on the seventh floor and holiday decorations throughout the store.

• Illuminate 900: The 900 North Michigan Shops host their annual Illuminate 900 holiday tree lighting tonight from 6 p.m. to 8 p.m. with family-friendly performances, seasonal activities, cookie decorating and photo moments throughout the atrium. Hosted by Giuliana and Bill Rancic, the event ends with Santa and a Make-A-Wish child lighting the 50-foot tree. Tickets are required.

Just For (Holiday) Fun

• Holiday Pop-Up Bars: It’s not the holiday season in Chicago without all the festive holiday bars! Chicago loves its special holiday pop-ups, and there are 20+ experiences that you can visit to enjoy festive drinks and decorations.

• Light Shows: Looking to see some holiday lights this year? There are great options including ZooLights at Lincoln Park Zoo, Santa’s Rock N Lights with locations near Wrigleyville and in Geneva, Light of Christmas at Guaranteed Rate Field, Illumination: Tree Lights at Morton Arboretum, Lightscape at Chicago Botanic Garden, Holiday Magic at Brookfield Zoo and more.

• Ice Skating: If you are looking to get out on the ice this holiday season, Chicago has a couple of iconic options. The McCormick Tribune Ice Rink opens tomorrow, Friday, Nov. 21 and is nestled right below The Bean at Millennium Park. Close by is the Skating Ribbon of Maggie Daley Park that allows you to skate through a fun course. Grab reservations before going!

• Winter WonderFest: Navy Pier’s family-friendly indoor holiday festival Winter WonderFest returns from Dec. 5 to Jan. 4 with rides, slides, inflatables, the kiddie train, bumper cars and ice skating. It features attractions like the Cliffhanger and Zero Gravity along with dozens of activities throughout the festival hall, and every ticket includes a ride on the Centennial Wheel for views of the pier’s holiday lights.

• Christmas Around the World: A fun, indoor holiday option for the whole family is the 83rd annual Christmas Around the World and Holidays of Light showcase at the Griffin Museum of Science and Industry. A massive four-story, floor-to-dome Grand Tree takes center stage and is surrounded by over 50 trees and displays that represent different holiday traditions from cultures around the world.

Chicago News

• Michelin List: The 2025 Chicago Michelin Guide came out this week. The biggest changes this year were Alinea losing a star, Kasama moving up to two stars and Feld earning its first star along with a Green Star for sustainability. Smyth is now the only three-star restaurant in the city, and Chicago has fifteen one-star spots overall. See the full list of Chicago Michelin restaurants.

• Digital IDs: Illinois Secretary of State Alexi Giannoulias’s office announced this week that residents can now add digital versions of their state IDs and driver’s licenses to Apple Wallet, with support for Samsung and Google devices coming next year. These mobile IDs can be used at TSA checkpoints at O’Hare and Midway and for age verification at places like restaurants and bars. They do not replace physical IDs, and you will still need to carry your physical card for situations like traffic stops or any instance where law enforcement requires it.

• Smoke Daddy: After 31 years in Wicker Park, Smoke Daddy announced yesterday that its original location will close after its final service on Sunday, Jan. 4, with a full calendar of events planned through the end of the year. The owners plan to open something new in the space, but haven’t shared what yet. The Wrigleyville location will remain open, and gift cards and rewards will continue to be valid at all 4 Star restaurants.

• Double Fun: A new neighborhood bar called Double Fun has opened in the Gold Coast from the team behind Sparrow and Bisous. Located on the corner of State and Elm at 2 W. Elm Street, it aims to reimagine the classic corner bar with a warm, seventies-inspired vibe, large windows and a lively atmosphere. The bar is open daily and offers happy hour from 4 p.m. to 6 p.m. Monday through Thursday and from 2 p.m. to 4 p.m. on Friday and Sunday.

• Chicago Sports: Clark the Cub was named the 2025 MLB Mascot of the Year, the State Farm Champions Classic will return to the United Center on Nov. 10, 2026 with a doubleheader featuring Duke, Michigan State, Kansas and Kentucky, the first-place Chicago Bears face the Pittsburgh Steelers this Sunday at Soldier Field (will this game take more years off our lives?) and Chicago will host Team USA vs Germany next summer ahead of the World Cup.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last week, we asked how you felt about the U.S. officially stopping the production of the penny. Here were the results:

1. 44%: Time to move on!

2. 34%: Bring back the penny!

3. 22%: I do not care.

Sunrise & Sunset in Chicago

Here is today’s outlook in Chicago (compared to last week):

• Sunrise: 6:46 a.m. (8 minutes later)

• Sunset: 4:25 p.m. (6 minutes earlier)

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