This coming week my husband and I will be returning to Chicago to visit family for Thanksgiving, as we did last year. I’ve been wondering what we might do to make the most of beginning the holiday season in this exciting metropolis. Last year we took in a performance of Dickens’ A Christmas Carol at the Goodman Theatre — a wonderful treat, but we didn’t want to simply repeat last year’s experience, especially when the city must have so much to offer.
Fortunately, a press release arrived in my inbox this week from the Chicago Loop Alliance, representing businesses and organizations in the bustling Loop district. The notice announced the group’s fourth annual Winter WonderLoop, heralding its “Random Acts of Holidays” as well as more than 100 special events, offers, promotions and destination suggestions from the alliances’ members. These include discounts on everything from stress-reducing massages, hotel rooms and special packages to a cupcake-decorating class and weekend parking.
I really liked the descriptions of some of those random holiday acts, occurring on Black Friday and every Saturday in December through December 22 from 11 a.m. to 4 p.m. One might enjoy free hot drinks and pastries, street performances courtesy of the Goodman Theatre or the Joffrey Ballet, bands and strolling carolers from local colleges and high schools, and free pop-up photo booths — props included.
If all that weren’t enough, the editors of Time Out Chicago, a visitors’ guide to the Windy City, compiled a list of 10 Wonders of the Loop. There are several I definitely would love to take in: checking out the window displays at Macy’s on State Street, browsing the booths of the Christkindlmarket at Daley Plaza, observing the “Wreathing of the Lions” on the front steps of the Art Institute, and ice skating in Millenium Park. And while I won’t be in town on December 18 to sing along with the pros at the “Do-It-Yourself Messiah,” I’d like to take part in the caroling, offered nightly from Thanksgiving through New Year’s Eve, at the iconic Cloud Gate (also known affectionately as “The Bean”) in Millenium Park.
That’s one of the delights of the holiday season: No matter where you find yourself this next month, you will likely be able to find plenty of activities and sights to take in which are unique to that place and special to the season. Check with a city’s visitors’ bureau or your hotel’s concierge to discover that holiday flavor.
— Patty Vanikiotis, associate editor/copy editor
Read This Next
4 Ways to Spend a Weekend in Cleveland, Ohio
Daily
Sep 23, 2026
Introducing
FX Excursions
FX Excursions offers the chance for once-in-a-lifetime experiences in destinations around the world.
#globility
Insta FeedDaily
Sep 23, 20264 Ways to Spend a Weekend in Cleveland, Ohio
Whether an adventure seeker, culturally curious or a lover of all things music, Cleveland, Ohio, is the perfect weekend getaway for all types of personalities and travel styles.
Sponsored Content
What Actually Happens If You Get Sick or Hurt on a Cruise?
You’ve booked your cabin, mapped the ports and packed the sunscreen. Hopefully, you also bought some insurance. But have you ever thought about what actually happens if a medical emergency strikes mid-voyage?
Daily
Sep 23, 2026Delve into a Curated Journey for Mexico City Art Week with Trip Whisperer
During Mexico City Art Week 2027 (Semana del Arte), Trip Whisperer founder Jessica Parker will lead Mexico City Art Week Salon, a small-group expedition to explore the city’s fascinating art, design, culinary and luxury lodging offerings. For five nights, Feb. 2–7, 2027, participants will lodge with creatives and like-minded travelers in Casa Amsterdam, a private Mexico City villa located in the La Condesa neighborhood. After daytime forays to explore the festival’s events, this group will return to the villa to enjoy mezcal tastings, chef-prepared dinners and evening activities.
eFlyer Reviews
Sep 23, 2026Review: Sage Lodge Resort & Spa
Set on more than 1,200 acres in Montana’s Paradise Valley, Sage Lodge sits just 30 minutes from Yellowstone National Park, with the Yellowstone River running for more than a mile along the property.
Sponsored Content
The World Awaits with Turkish Airlines’ Global Access
Turkish Airlines enjoys the unique position as the airline flying to more countries than any other airline. Its unrivaled global reach is only the beginning of the experience that awaits passengers with Turkish Airlines.
Airlines
Sep 23, 2026American Airlines, Condor Airlines Announce New Interline Agreement
American Airlines and Condor Airlines expand their international partner network with a new interline agreement, providing travelers with a wide range of new connections. Passengers can expect connections to more than 150 cities through Condor’s trans-Atlantic gateways in major hubs like JFK, BOS and LAX.
Daily
Sep 23, 2026What’s in Store for Finnair in 2026/2027?
Global Traveler recently sat down with Finnair’s president and CEO Turkka Kuusisto, and Päivyt Tallquvist, senior vice president of communications, to discuss the airline’s past year and its future developments.
Sponsored Content
Why Japan Is Best Explored by Sea with Princess
Japan is a destination that rewards repeat visits because no two regions — or seasons — feel quite the same. One moment, you’re wandering through centuries-old geisha districts in Kanazawa. The next, you’re watching neon reflections dance across Tokyo streets long after midnight.
Daily
Sep 22, 2026Cunard’s “Queen Mary 2” to Undergo Stunning Refurbishment
Cunard recently announced a stunning refurbishment of Queen Mary 2; the ship prepares to enter dry dock on March 31, 2027, as the flagship of the Cunard fleet and the only ship in the world offering regularly scheduled trans-Atlantic crossings between Southampton and New York. The refurbishment will introduce new Grill Suites, an elevated wellness offering, enhanced retail spaces and refreshed guest areas, while preserving the ship’s Art Deco identity. The ship will return to service May 9, 2027.
ShareThis