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
Introducing
FX Excursions
FX Excursions offers the chance for once-in-a-lifetime experiences in destinations around the world.
#globility
Insta FeedDaily
Sep 24, 2026Kimpton Mirador Pacific Grove Adds New Amenities, Programming
Opened in early 2026, Kimpton Mirador Pacific Grove continues its momentous year with newly added amenities and programming. Located in one of California’s most charming and culturally rich coastal towns, the hotel brought a new luxury lifestyle offering and a fresh spirit to the Monterey Peninsula.
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.
Daily
Sep 24, 2026This Beijing Hotel Makes Top 10 in 50 Best Hotels of 2026
Moving up from its No. 14 debut ranking in 2025, Mandarin Oriental Qianmen, Beijing secured seventh on Forbes’ The 50 Best Hotels list this year.
Daily
Sep 24, 2026Bathhouse to Open First Philadelphia Location at The Bellevue
New York City-based social wellness brand Bathhouse, beloved for its modern take on sauna culture, celebrated its first expansion beyond the Big Apple with its debut in Center City Philadelphia at The Bellevue.
Sponsored Content
IHG Business Edge: A Smarter Way for Small- and Mid-Sized Businesses to Travel
IHG Business Edge is a complimentary travel program designed to help small- and mid-sized businesses manage travel more efficiently while saving on hotel stays. Members enjoy access to guaranteed discounts, loyalty benefits, and partner offers across IHG Hotels & Resorts’ global portfolio of 7,000-plus hotels in more than 100 countries.
Daily
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.
Review: Sage Lodge Resort & Spa
eFlyer Reviews
Sep 23, 2026eFlyer Deals
Sep 23, 2026Save on Stays at Independent Collection Hotels & Resorts with Fall Sale
Dive into fall with Independent Collection’s exclusive sale across a wide range of resorts and hotels.
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.
eFlyer Deals
Sep 23, 2026Earn Limited-Time Bonuses from Chase Air Canada Aeroplan Card
Chase and Air Canada embrace autumn with refreshed benefits to newly named Chase Air Canada Aeroplan Card. Additionally, new cardmembers can earn Chase Aeroplan’s best offer ever.



ShareThis