Few American cities approach Christmas with the distinctiveness of Chicago.
Downtown — the Loop, as locals call it — is lit with seasonal decorations, State Street fills with shoppers, and Millennium Park draws visitors with its outdoor skating rink and illuminated Christmas tree.
This year’s start to the season also came with a stark reminder of Chicago’s public safety concerns.
I spent last weekend in the Windy City and woke up the morning of Saturday, Nov. 22, to reports of a mass shooting the night before on State Street in front of the landmark Chicago Theatre and just down the block from the world-famous Macy’s store.
I had walked that stretch of street earlier, taking in the crowds and storefront displays. By the time the shooting occurred, shortly before 10 p.m., I was already back in my room at the Allegro Royal Sonesta a few blocks away.
Learning what had happened overnight was jarring and made me more cautious of other festivities and large gatherings, including the Magnificent Mile Lights Festival. It also underscored a broader reality: Chicago, even during the holidays, continues to struggle with persistent crime.
Considering what happened, it’s fair to ask whether I can even recommend visiting Chicago. My answer is simple: yes, the city remains worth visiting. The reality is we live in a fallen world. Bad things can and do happen anywhere.
One of the best examples of how well Chicago does Christmas is the Christkindlmarket.
Held since 1996, its main location at Daley Plaza sits beneath the Richard J. Daley Center and directly across the street from the Sky Chapel at First United Methodist Church. Modeled after German Christmas markets, vendors in traditional wooden stalls sell German food, ornaments, nutcrackers, nativity figures and other seasonal items. Lines often wrap around the block as people wait for glühwein (mulled wine) served in collectible mugs.
Shopping has long been part of Chicago’s holiday appeal.
The Macy’s on State Street still draws traffic, but the store today feels faded and removed from the grandeur of its predecessor, Marshall Field’s.
Along Michigan Avenue, it’s a completely different experience. The Magnificent Mile features considerably higher-end stores and brands. Its seasonal window displays and outdoor decorations feel more cohesive and better maintained.
If you go
In addition to the Christkindlmarket at Daley Plaza, there are two satellite locations: Wrigleyville and suburban Aurora. The Daley Plaza market runs through Dec. 24. Operating hours are 11 a.m. to 8 p.m. Sunday through Thursday and 11 a.m. to 9 p.m. on Friday and Saturday. Admission is free.
St. James Cathedral (Episcopal) will hold a special Festival of Nine Lessons and Carols on Dec. 21 at 4 p.m., preceded by an organ prelude at 3:30 p.m. The service is modeled after the famed liturgy at King’s College, Cambridge. A couple of blocks away at Fourth Presbyterian Church (PCUSA), the 9:30 a.m. and 11 a.m. services that same day will feature the morning choir performing a Christmas cantata with members of the Civic Orchestra of Chicago. The music will include Bach’s “Magnificat.”
Meanwhile, Holy Name Cathedral (Roman Catholic) has its 6th Annual Rector’s Christmas Concert featuring Rich Daniels and members of the City Lights Orchestra at 7 p.m. Dec. 12. Tickets are free, but registration is required.
Other recommended activities and attractions include the Art Institute of Chicago with its world-class impressionist collection, the Field Museum of Natural History and the Griffin Museum of Science and Industry. Also recommended are any of the architectural tours offered by the Chicago Architecture Center. Buying a CityPass card is worth the investment if you’re doing multiple fee-charging attractions.
During my four-night stay, I experienced two self-styled boutique hotels: the Allegro Royal Sonesta and the Staypineapple.
The Allegro’s amenities and services felt more limited than what you’d expect from a four-star property. The Staypineapple delivered a bit more — including several thoughtful extras that many hotels have dropped since the pandemic — although it felt more like a short-term vacation rental than a traditional hotel. Some rooms at the Staypineapple feature seasonal Christmas decor, including lighted trees.
Both properties enjoy convenient locations in the heart of the Loop. Full trip planning resources are available through Choose Chicago.
Dennis Lennox writes a travel column for The Christian Post.
