Holiday Happenings in the City: Chicago Markets, Pop-Ups, Performances, Walking Tours, Train & Hot Tub Boat Rides

It’s not too soon to start making a list and checking it twice for what’s happening in Chicago this holiday season. Here are some suggestions from Choose Chicago.

HOLIDAY MARKETS

The Chicago Christkindlmarket is delighted to announce the return of its cherished holiday tradition for its 29th season at Daley Plaza in Chicago, its 4th year at RiverEdge Park in Aurora, and its return to Gallagher Way in Wrigleyville. The Chicago and Aurora locations will open on November 21, 2025, while Wrigleyville will welcome visitors starting November 23, 2025. All three markets are admission-free, featuring authentic vendors, live entertainment, and special events to create a festive holiday atmosphere. 

HOLIDAY POP-UPS

  • Jack Frost’s Pop Up – Returning November 2025 
  • Frosty’s – Returning November 2025 
  • Santa Baby – Returning November 2025 
  • Elf’d Up– Returning November 8, 2025 
  • Château Carbide Winter Garden at The Pendry Chicago (Launching Nov. 20 | 5 pm-12 am) – Château Carbide is launching their rooftop winter haven for another season with an all-new twist you won’t want to miss! Make a reservation for a private lodge and enjoy winter-inspired small bites and seasonal cocktails while taking in the stunning city-wide views of Chicago and all its snowy splendor.

HOLIDAY SHOWS & PERFORMANCES 

TOURS & ACTIVITIES

Bobby’s Bike Hike Holiday Hike: Season Sampling Food & Walking Tours begin at the end of November and run through Christmas Eve. See the lights of the Magnificent Mile, the ice skating rink and Christmas tree in Millennium Park, enjoy a warm and filling deep dish pizza, experience the German-inspired festivities of Christkindlmarket, and toast to a joyful season over a seasonal beverage! This 3 hour Chicago holiday tour is perfect for families, friends, holiday parties, and anyone looking to celebrate the season in an exciting new way. All food & non-alcoholic beverage samples included in ticket price. (Pricing starts at $74.99.)

Chicago Boat Company’s Hot Tub Boats, returning this winter with their launch in November (exact timeline and hours to come). Departing from Marina City (300 N. State St.), guests can take out a Hot Tub Boat for up to 90 minutes with as many as six guests per boat. They’ll cruise along the Chicago River, taking in iconic skyscraper views and, in December, the city’s festive décor and holiday cheer from river level. Each boat comes equipped with a Bluetooth speaker and is BYOB, with plenty of cooler space and floating cup holders. Hot chocolate, hot apple cider, mulled wine, you name it! 

The Christmas Tree Crawl: The Magic of Chicago at the Holidays – Let Inside Chicago Walking Tours take you on an enchanting stroll through the heart of the city at its prettiest time — during the winter holiday season.  On this nostalgic and educational tour, we will lead you on a “Christmas treasure hunt” through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown. You’ll learn about the origins of some world-famous Christmas characters — some of them from Chicago, some not — as well as the history behind Christmas traditions practiced by people around the world. [November 28 – December 20, 2025; available Thursdays-Saturdays]

  • We call this tour a “pop-up tour” because it’s offered for a  limited time, because we want to show off the city’s beauty at this time of year. You won’t find a boat, a bus, or even a segway where we’re going.  

It’s the most wonderful time of the year! Chicago’s most unique and beloved holiday tradition is here: The Allstate CTA Holiday Fleet. Now in its 33rd year of operation, we are excited to be delivering holiday cheer throughout Chicago’s neighborhoods and welcome you aboard our decked-out and dazzling Allstate CTA Holiday Train and the popular Allstate CTA Holiday Bus!

Christlkindlemarket. Photo courtesy of Choose Chicago.

About Choose Chicago

Choose Chicago is the official sales and marketing organization responsible for promoting Chicago as a global visitor and meetings destination, leveraging the city’s unmatched assets to ensure the economic vitality of the city and its member business community. Follow @choosechicago on Facebook, Instagram, Twitter, LinkedIn, and TikTok. For more information, visit choosechicago.com.

“BOO-ling Green” Is Home to Bushels of Fall Fun for Families

Over the past few years, we’ve been telling you about the frightful amounts of fall fun visitors can have when they come to Bowling Green, Kentucky, the childhood home of horror film director John Carpenter.

This year, though, we’re taking the scare level back to a G-rating as we provide a glimpse into the more family-friendly aspects of a fall trip to Kentucky’s third-largest city. And by G-rating, we mean you’ll find the three best G’s of the season … gourds, goodies and ghosts.

To us, the perfect weekend getaway in Bowling Green with your little goblins includes these highlights:

GOURDS

Fall is the perfect time to visit Jackson’s Orchard, which is home to both a pumpkin patch and pick-your-own orchard. Credit: VisitBGKY

Jackson’s Orchard & Nursery: Since 1966, the Jackson family has been welcoming visitors to their farm. Running every Saturday (from 9 a.m. to 5 p.m.) and Sunday (from 1 to 5 p.m.) in October, the orchard’s Pumpkin Festival means hayrides to the pumpkin patch, corn maze and pick-your-own apple orchard; games; pony rides; a petting zoo; and an array of fantastic food. (Insider tip: Do NOT miss the caramel apples.)

Scarecrow Trail at Lost River Cave: The cave, which runs underneath downtown Bowling Green and is visited via a boat (yes!) is a fantastic experience all year round … but especially in this season when we’re all ready to have a little fun in the dark. But there’s also above-ground entertainment here in the form of walking trails, which get even more perfect in the fall.

That’s when local families, businesses and organizations create themed scarecrows to greet visitors. Between October 4 and 26, from dawn to dusk, you can see about 90 scarecrows and vote on your favorites. And this is no trick but all treats: The trail is totally free, though you’re welcome to make a donation if you’d like.

GOODIES

Chaney’s Dairy Barn: If you crave seasonal flavors and also want to hang out with some big, fuzzy creatures (we’re talking about cows here, not monsters), you won’t want to miss one of the region’s most popular agritourism destinations. Chaney’s offers a self-guided farm tour so families can get a glimpse at how milk gets from cows to grocery stores. They also have a stellar playground, and this time of year, there’s a cow-themed corn maze. There’s a restaurant on site (go for the gourmet grilled cheese – you’re at a dairy farm, after all), but let’s face it, all that is just a prelude to the reason you’re really here … the fresh ice cream. You can choose from more than 50 flavors and won’t go wrong with a single one, though we suggest you lean into fall and make at least one of your scoops (because nobody does a single here) either apple pie or pumpkin.

Meltdown Ice Cream & Soda Fountain: Not to be outdone by what you’ll find on the farm, this iconic ice cream parlor in the heart of downtown also offers an array of seasonal flavors. Starting this month, those include Hello, Pumpkin (self-explanatory); Apple Butter Biscuits, which is sweet cream with apple butter swirl and biscuit cookies; and Pumpkin Un-roll, a cream cheese ice cream with pumpkin roll cake and pumpkin butter swirl. With flavors like that, you’ll want to go for THREE scoops! The shop also offers fall-themed ice cream floats, of course!

Our PR pal in Bowling Green made the ultimate sacrifice and stopped by Meltdown on Tuesday night.
That’s Hello, Pumpkin on the left and Apple Butter Biscuits on the right. Credit: Carrie Cavitt

GHOSTS

Photo courtesy of UnSeen BG Tour.

UnSeen BG Tour: These themed history tours are always a hit with visitors, and this year brings the debut of a new ghostly tour that’s family-friendly, “Phantasms Around Fountain Square.” Guides take participants on a 1.5-mile walking tour that explores the haunted history in and around the city’s iconic Fountain Square. Tours depart at 7 p.m. on weekends throughout October.

Dr. Smith’s Spooky Stories: If you want to check out what most people consider the most haunted spot in town, you need to head to Western Kentucky University, nicknamed “The Hill.” That’s where Dr. Tamela Williams Smith, who’s had an interest in the paranormal since she was a student there, shares the stories she’s learned by conducting interviews with at least 100 students, faculty members and staff. The university is home to an array of unexplained phenomena, and this year Dr. Smith has adapted her standard “Hilltop History and Haunts Tour” to create a more kid-friendly ghost adventure, too.

White Squirrels: Are they ghosts? No! But do these tiny rodents look like they’re ready to trick-or-treat? They sure do. Bowling Green’s favorite animals are the rare white squirrels found in abundance here. A great place to see them is on the campus of Western Kentucky University, where they’re revered.

To start scaring up some G-rated fun for your family on a fall visit to Bowling Green, check out www.visitbgky.com.

This is not a ghost.

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Exploring Louisiana’s Cajun Bayou for Food, Fun, History & More

The Louisiana’s Cajun Bayou Tourism recently announced its new tourism campaign, “Geaux Bold,” encouraging visitors to immerse themselves in a destination that doesn’t hold back and where the authentic spirit of the people who have set this region apart live an unapologetically bold approach to life.

Lafourche Parish, popularly referred to as “Louisiana’s Cajun Bayou,” is located less than an hour’s drive from New Orleans, but it’s light years away in terms of experiences. Life along Bayou Lafourche is simultaneously laid-back and full of excitement, and the bold personalities who live here are eager to introduce visitors to their unique world. It’s a cultural experience unlike anything else in the United States.

The original bold explorers were the Acadians who settled here about 250 years ago, forging a new life in the face of adversity. Their strength of character, refusal to relinquish their traditions, and ability to both work and celebrate hard are all woven into the region’s DNA.

For those unfamiliar with the term (read: those living outside Louisiana), “geaux” is a playful version of the word “go” … spelled with a French twist. It’s what you’ll hear fans screaming at sporting events throughout Louisiana, including the local university, Nicholls State.

“When deciding on a new marketing campaign, we wanted to focus on the experiences that truly resonated with our visitors and highlighted our Cajun culture,” says Ian Wallis, Sales & Marketing Manager at Louisiana’s Cajun Bayou Tourism. “When we looked at everything one can do in Lafourche Parish, it was a no-brainer that the focus of the new campaign needed to emphasize the incredible amount of bold things our parish has to offer.”

To “Geaux Bold” means paddling through the untamed waterways of Bayou Lafourche, keeping an eye out for the birds above and the alligators lurking at the water’s edge, or sampling authentic Cajun dishes prepared by chefs whose recipes have been passed down from their maw maws and paw paws. It means heading to a festival, letting the music flow through you and learning how to dance like the Cajuns do, or casting a line into the Gulf and reeling in scale-tipping fish. It means celebrating Mardi Gras with people who were strangers this morning and who now feel like family, or strolling through historic sites to learn about the incredible assortment of people who came together in this unique destination to create a “cultural gumbo.”

The new campaign from Louisiana’s Cajun Bayou encourages travelers to come get a taste of both the literal and figuratively bold flavors of the bayou. All they need to pack is a sense of adventure … and probably their stretchy pants.

The new campaign brings with it updated designs for the tourism office’s visitor guide and newsletter, plus a new look for the coveted Cajun Bayou Food Trail T-shirt, which is awarded to visitors who pick up a Food Trail passport and get it stamped at any five of the 18 participating restaurants or six food-related special events.

For more information about planning a trip to Louisiana’s Cajun Bayou, start at www.lacajunbayou.com. And while you’re in the area, be sure to stop by the all-new Cajun Bayou Visitor Center, which offers an interactive introduction to Lafourche Parish and which will help you boldly plan your visit.

Photos courtesty of Louisiana’s Cajun Bayou Facebook Page.

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 An Enchanting Journey: Exploring Hungary’s 1000-Year-Old Wine Culture

For over 1,000 years, civilizations have produced quality wine in the Tokaj region of modern-day Hungary. This area’s deep winemaking history and cultural significance in Central Europe have led it to be listed as one of the country’s eight UNESCO World Heritage Sites.

The most revered wine from this area is Tokaji wine, a sweet dessert wine that is even mentioned in the country’s national anthem.

The region is comprised of 5,500 hectares of vineyards stretching across 27 municipalities, with volcanic soil that provides the ideal conditions for grapes to develop noble rot, a fermentation process characteristic of Tokaji wine that contributes to its distinct taste.

Today, these vineyards allow visitors to taste their wine straight from the source while taking in the views of Hungary’s historic rolling hills.

Here are a few of the vineyards that make Hungary’s Tokaj Wine Region special: 

  • Götz Winery: Looking straight out of a movie, this vineyard’s “hobbit-hole” cellars contributed to the area’s UNESCO World Heritage Site status. Like many in the region, the Götz Winery’s specialty is the area’s distinct Tokaji Aszú grapes, producing the iconic Tokaji wine. The winery is located in the 18th-century village of Hercegkút, providing amenities to tourists who visit the region. The deceivingly spacious cellar can seat up to 200 people, making this a fantastic space for large events. 
  • Disznókő Winery: Originally founded in 1413, Disznókő Winery is one of the Tokaj Wine Region’s most distinguished vineyards. This esteemed winery has gained national and international attention, having been named “Hungarian Winery of the Year” in 2005, cementing its place as a must-visit for enotourists in the region. Disznókő Winery’s 150 hectares of land make for an incredible visitation experience and allow for a large variety of grapes planted, creating special blends that can’t be found in other Tokaj vineyards. 
  • Barta Winery: Home to a stunning 17th-century aristocratic mansion, this historic vineyard continues its timeless organic cultivating methods. As stated, Barta’s philosophy is: “If we cultivate the vineyard in an environmentally friendly way, we should also make our wine the most natural, most traditional way possible.” The mansion has three recently renovated suites for guests to spend the night, a built-in cellar carved into the bedrock, and a rustic tasting room. 
  • Gróf Degenfeld Wine Estate and Castle Hotel: This spectacular vineyard is home to a 19th-century chateau hotel, a luxury restaurant, and all the wine anyone could dream of consuming. The sprawling 35-hectare property produces different kinds of wine, from traditional Tokaji sweet wines to dry wines like Muscat Blanc, all made using the same unique processes for over 500 years.  

Exploring Tokaj is not only a journey through one of the world’s most historic wine regions, but also an invitation to experience Hungary’s living cultural heritage firsthand. With its award-winning vineyards, historic estates, and unforgettable flavors, Tokaj offers travelers a truly timeless taste of Central Europe. 

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