Category: Entertainment

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

Chicago Neighborhoods, Chicago Parks, Chicago River, Christkindlmarket, Christmas, Entertainment, Holiday, Holiday events, Holiday Travel, Hot Tub Boat Rides, Pop-ups, Pop=ups, Train rides, Uncategorized

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.

‘Paranormal Activity’ haunts Chicago Shakespeare Theater

Entertainment, Theater

By Guest Blogger Eloise Marie Valadez

Something spooky is definitely invading a prominent stage in Chicago.

It’s “Paranormal Activity” and it’s taking place at The Yard at Chicago Shakespeare Theater on Navy Pier through Nov. 2. The North American premiere production, which is an original story, is based on the popular film franchise.

@chicagoshakes

Even if you see it, you may not believe it. See PARANORMAL ACTIVITY at Chicago Shakes! 🎟️ chicagoshakes.com #paranormalactivity #theater #horrortok

♬ original sound – Chicago Shakespeare

The show, written by Levi Holloway, is directed by Felix Barrett. Spectacular illusions by Chris Fisher star in this production as well.

Audience members who want to be in suspense throughout a theatrical presentation will, no doubt, be at the edge of their seats here. “Paranormal Activity” tells the story of husband and wife James and Lou, who have moved to London from Chicago to pursue a new life and get away from “something” in their past.

There are many fascinating illusions, haunting sounds and other frightening scenes throughout “Paranormal Activity” to keep theatergoers’ attention. All eyes and ears will be focused on the mysterious  happenings on stage.

A strong cast helps make this production a winner and one not to be missed. Starring in “Paraniormal Activity” are Cher Alvarez as Lou, Patrick Heusinger as James, Shannon Cochran as Carolanne, Kate Fry as Etheline Cotgrave and Sophie Kaegi in an ensemble role.

After its Chicago run, the play will be performed in Los Angeles, Washington D.C. and San Francisco.

FYI: “Paranormal Activity” runs to Nov. 2 at The Yard at Chicago Shakespeare Theatre at Navy Pier. Visit chicagoshakes.com for more information.

For more information about what to do in Chicago, visit Choose Chicago.

About Eloise Marie Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food, is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written word.

Sound of Music: One of the most beloved musicals currently graces the stage in The Windy City

Entertainment, Musical, Theater

By Guest Blogger Eloise Marie Valadez

The Rodgers and Hammerstein gem “The Sound of Music” continues through Nov. 2 at the James M. Nederlander Theatre in Chicago. This national North  American tour is being presented by Concord Theatricals NETworks Presentations and Broadway in Chicago.

“The Sound of Music tells the story of the Von Tapp Family singers. It revolves around Maria, who is in “training” to become a nun, and also pursues a job as a governess for Captain Von Trapp’s children. It’s a tale of family togetherness, love and a fondness for music and what music can bring to a home.

The production, which is directed by Jack O’Brien, celebrates the 65th anniversary of the original stage debut of “The Sound of Music.”

Starring as Maria is Cayleigh Capaldi, who exhibits exceptional vocal talents. Also offering strong vocals are Christiane Noll as Mother Abbess, Kevin Earley as Captain Georg Von Trapp and the cast of young singers who star as the Von Trapp children.

When it comes to soundtracks, “The Sound of Music” is a winner. Almost every tune is a favorite of theatergoers. And it’s difficult to keep from singing along during this show.

Among outstanding numbers are “My Favorite Things,” “Maria,” “Climb Every Mountain,” “Do-Re-Mi,” “Edelweiss” and the title tune “The Sound of Music.”

Theater fans will surely want to plan a visit to the theater to enjoy this production.

FYI: “The Sound of Music” continues to Nov. 2 at the James M. Nederlander Theatre, 24 W. Randolph, Chicago. Tickets are $40 to $140. Visit broadwayinchicago.com.

Puppetry reigns in Disney’s The Lion King

Cadillac Palace Theatre, Dance, Entertainment, Musical, Uncategorized

By Guest Blogger Eloise Marie Valadez

A majestic production is gracing the stage in Chicago.

“The Lion King” is currently running through Oct. 19 at Chicago’s Cadillac Palace Theatre. The show is a must-see production and shines on stage with a colorful set, fascinating costumes, creative puppetry elements and a strong cast.

In promotional materials for the show, it’s touted as “the world’s #1 musical” and that’s definitely not hype. “The Lion King” surely draws audience members in with its strong theatrical elements from powerful vocals, colorful sets, a standout soundtrack and more.

“The Lion King” tells the story of the young cub Simba, who after the death of his father Mufasa, must eventually take control of the throne. There are many adventures awaiting Simba as he grows and he must battle his evil uncle Scar on his way to the throne.

This hit production has been touring North America for nearly 25 years and has been capturing theatergoers’ hearts throughout its celebrated run. It originally opened on Broadway on Nov. 13, 1997.

Starring in the current touring production are Peter Hargrave as Scar, David D’Lancy Wilson as Mufasa,, Mukelisiwe Goba as Rafiki, Robert Creighton as Timon, Nick LaMedica as Zazu, Danny Grumich as Pumbaa, Gilbert Domally as Simba and Thembelihle Cele as Nala.

Standout out musical numbers include “Circle of Life,” “Hakuna Matata,” “I Just Can’t Wait To Be King” and “Can You Feel The Love Tonight.”

FYI: “The Lion King” continues to Oct. 19 at Cadillac Palace Theatre, 151 W. Randolph St., Chicago. Tickets are $45 to $180. Visit BroadwayInChicago.com.

About Eloise Marie Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food, is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written word.

Elizabeth McGovern shines as Ava Gardner in new play

Entertainment, Theater

By Guest Blogger Eloise Marie Valadez

Legendary Hollywood actress Ava Gardner is the subject of a new play at Chicago’s Studebaker Theater in the Fine Arts Building.

 “Ava: The Secret Conversations,” starring award-winning actress Elizabeth McGovern, continues to Oct. 12. The show, written by McGovern, whom film and TV fans will know from starring roles in “Downton Abbey,” “Once Upon A Time in America” and “Ordinary People,” sheds a fascinating light on the late film legend.

Elizabeth McGovern and Aaron Costa Ganis are seen in “Ava: The Private Conversations.” Provided photo.

The play is based on interviews Gardner gave to writer Peter Evans for a book that was to be published about her. Although it was initially banned from publication, the book was printed 25 years later.

In the show, audience members are led on a journey through segments of Gardner’s career and her marriages to Mickey Rooney, Frank Sinatra and Artie Shaw as well as her relationship with the eccentric Howard Hughes.

Elizabeth McGovern. Photo provided.

McGovern, who hails from Evanston, Illinois, offers a stellar performance as Gardner in this show, directed by Moritz von Stuelpnagel. Starring as writer Evans is Aaron Costa Ganis. Ganis also portrays Rooney, Sinatra and Shaw. It’s fascinating to watch as he shifts from one character to another.

“Ava: The Secret Conversations” is making its Chicago premiere. It originally played at NY City Center. Don’t miss this interesting look at retro Hollywood and one of its most glamorous stars.

FYI: “Ava: The Secret Conversations” continues to Oct. 12 at The Studebaker Theater in the Fine Arts Building, 410 S. Michigan Ave., Chicago. Tickets are $40 to $170. Call 312-753-3210, ext. 102. Visit AvaGardnerPlay.com.

About Eloise Marie Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food, is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written word.

Joffrey Ballet delivers passionate, exceptional ‘Carmen’

Dance, Entertainment, Joffrey Ballet

By Guest Blogger Eloise Marie Valadez

The Joffrey Ballet recently opened its 70th season with the U.S. and Joffrey premiere of the outstanding ballet “Carmen.”

Victoria Jaiani and Dylan Gutierrez are seen in “Carmen.” Photo provided by The Joffrey Ballet© Cheryl Mann 2025

“Carmen,” starring choreography by Liam Scarlett, continues to Sept. 28 at The Lyric Opera House in Chicago. Scarlett is also the choreographer of the acclaimed ballet “Frankenstein.”

The story of “Carmen” revolves around a seductive gypsy named Carmen, who causes mayhem in the life of soldier Don Jose, leading to a complicated love triangle, destructive relationships and tragedy.

With the Joffrey Ballet at the helm of this story, this theatrical  production soars with skillful and dynamic dance moves. The musical score by Georges Bizet shines as well.

“Carmen” originally had its debut in 2015 by the Norwegian National Ballet.

Starring as Carmen in the Joffrey’s opening night production was Victoria Jaiani, who offered a passionate, sultry and engaging performance. Dancers Alberto Velazquez as Don Jose and Dylan Gutierrez, as the bullfighter Escamillo, proved powerful in their roles as they executed energetic leaps, turns and other dynamic dance moves.

Kudos to the entire troupe for its terrific performance throughout the full-length ballet. The Joffrey Ballet never fails to draw audiences in with their adept performances.

FYI: “Carmen,” by The Joffrey Ballet, continues to Sept. 28 at the Lyric Opera House, 20 North Upper Wacker Drive, Chicago. Visit joffrey.org.

About Eloise Marie Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food, is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written word.

Top photo: Victoria Jaiani stars in The Joffrey Ballet’s “Carmen.” Photo by Cheryl Mann.

 ‘MJ the Musical’ sizzles in return Chicago engagement

Entertainment, Musical, Theater, Uncategorized

By Guest Blogger Eloise Marie Valadez

Magical moves and a stellar collection of songs are taking the spotlight on stage at Chicago’s James M. Nederlander Theatre.

“MJ the Musical” has returned to The Windy City on the First National Tour and is energetically relaying the life story and career of the iconic entertainer Michael Jackson. The show runs through Aug. 24.

Jordan Markus stars as Michael Jackson in “MJ the Musical.” Photo by Matthew Murphy.

In this production, which is directed and choreographed by Christopher Wheeldon with book by Lynn Nottage, Jackson is seen preparing for his massive 1992 Dangerous tour, which had immense risks and stresses as it was mounted. While he’s rehearsing for the tour, a cameraman and reporter are allowed in to document the making of the tour and to interview Jackson about his work, the inspirations for his music and thoughts about his fame and career.

As the show goes on, the audience journeys to all stages of Jackson’s career from his days as a youngster with the Jackson 5 to his various solo work as well as his relationship with his family and his domineering father.

Pictured is a scene from “MJ the Musical,” currently in Chicago. Photo by Matthew Murphy.

Jordan Markus stars as MJ. The dancer/singer proves he’s perfect for the role as he slides artistically across the stage interpreting Jackson’s moves smoothly. Markus’ vocals are dynamic and he definitely does justice to Jackson’s tunes.

Kudos also to Devin Bowles for his strong performance as Joseph Jackson. Bowles also performs as tour director Rob. Among other performers starring in “MJ” are Melvin Gray Jr., Quentin Blanton Jr., Bryce A. Holmes, Erik Hamilton, Brandon Lee Harris, Kristin Stokes, Kevin Cruz, J. Daughtry and others.

Outstanding musical numbers include “Billie Jean,” “Smooth Criminal,” “Dancing Machine,” “Thriller,” “Wanna Be Startin’ Somethin'” and “I Want You Back.”

“MJ” is truly the celebration of the music of an entertainment genius.

FYI: “MJ the Musical” continues to Aug.24 at James M. Nederlander Theatre, 24 W. Randolph St., Chicago. Tickets range from $49-$153. Visit BroadwayInChicago.com.

Top photo: Jordan Markus with “MJ” in the first national tour of “MJ.” Photo by Matthew Murphy.

About Eloise Marie Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food, is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written word.

 ‘Twisted Melodies” showcases the genius of musician Donny Hathaway

Chicagoland Area, Entertainment, Musical, Theater

By Guest Blogger Eloise Marie Valadez

The latest production to hit the stage at Northlight Theatre tells the story of the life of singer/songwriter Donny Hathaway.

“Twisted Melodies,” written by Kelvin Roston Jr., is directed by Ron OJ Parson and associate director Alexis J. Roston. The one-man show, which recounts one day in Hathaway’s life, is superbly acted by Roston, who has previously performed this acclaimed show in the Chicago area.

The production does an excellent job at presenting the life of Hathaway, who was tormented by emotional and mental illness, in a compassionate way on stage.

Hathaway’s struggles with paranoid schizophrenia interfered with his work as a musician and his ability to live everyday life but “Twisted Melodies” shows that his music was a place he could retreat into to find a little peace.

Roston’s acting abilities are strong as he displays the torment Hathaway goes through. Roston’s singing voice is excellent as well. Hathaway, who hailed from Chicago died in 1979 after jumping from his room at the Essex House Hotel in New York City.

The show not only features some of Hathaway’s compositions but also talks about his relationship/partnership with singer  Roberta Flack.

“Twisted Melodies” ends Northlight’s 2024-2025 season.

FYI: “Twisted Melodies” runs through Aug. 10 at Northlight Theatre, 9501 Skokie Blvd., Skokie. Visit northlight.org.

Black Ensemble Theater puts a spotlight on three legendary singers

Entertainment, Theater

By Guest Blogger Eloise Marie Valadez

The music of beloved singers Gladys Knight, Patti Labelle and Dionne Warwick is being celebrated at Black Ensemble Theater (BET) in Chicago.

“That’s What Friends Are For,” the latest production at BET, runs through Aug. 10. The show tells a fictional tale of singers Knight, LaBelle and Warwick gathering together backstage prior to a planned Las Vegas residency. They talk about their lives and the friendship they share.

The show, produced by Black Ensemble Theater founder Jackie Taylor, is written and directed by Daryl Brooks. It’s an energetic production featuring powerful vocals from the talented ensemble cast.

“That’s What Friends Are For” stars Rose Marie Simmons as mature Gladys; Michaela Dukes as young Gladys; Sybyl Walker as mature Dionne; Brianna Buckley as young Dionne; Tamara Batiest as mature Patti; Courtney Driver as young Patti; Dennis Dent as Charles Gibbons; Dwight Neal as Luther Vandross; Jaimee Thomas as Michael Peterson and Treqon Tate (ensemble).

Among highlighted numbers are the engaging “That’s What Friends Are For,”  “You Are My Friend,” “If Only For One Night,” “Midnight Train To Georgia” and “Walk On By.”

Audience members will leave the theatre singing the tunes of these iconic musical artists.

FYI: “That’s What Friends Are For,” will run through Aug.10 at Black Ensemble Theater, 4450 N. Clark St., Chicago. Visit blackensembletheater.org.

About Eloise Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food, is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written word.

Chicago Shakespeare Theater’s ‘Billie Jean’ tells powerful story of tennis icon

Entertainment, Theater

By guest blogger Eloise Marie Valadez

The stage of Chicago Shakespeare Theater’s The Yard is currently set as a tennis court. And on that court the impactful story of tennis legend Billie Jean King is being played out. 

“Billie Jean,” which is a world premiere production, continues through Aug. 10 at Chicago Shakespeare Theater. The play was written by Lauren Gunderson and directed by Marc Bruni. “Billie Jean” was produced and developed in collaboration with Harriet Newman Leve, Stephanie Sandberg, Lily Tomlin and Jane Wagner.

The show relays the story of King as she goes from a young girl pursuing her dreams to the woman who becomes not only a champion of the game of tennis but a champion for equality on all levels, specifically with women’s rights on the sports field and in business.

Giving powerful performances are Chilina Kennedy as Billie Jean King and Dan Amboyer as her husband Larry King. Also starring in the cast are Julia Antonelli, Elena Hurst, Courtney Rikki Green, Wynn Harmon,  Carolyn Holding, Jurgen Hooper, Callie Rachelle Johnson, Lenne Klingaman, Nancy Lemenager and Murphy Taylor Smith.

“Billie Jean” has no lulls and definitely keeps an audience’s attention.

About the show, playwright Gunderson says, “CST is the perfect place to launch this new play about Billie Jean King, her activism, and her ongoing impact on the world. Her story is a hero’s journey, and the house of Shakespeare’s heroes is a fitting home for this theatrical debut about excellence, equality, and heart.”

To learn more about “Billie Jean,'” visit chicagoshakes.com.

About Eloise Marie Valadez

Guest blogger Eloise Marie Valadez, a frequent contributor to Travel/Food is a professional journalist/writer and editor with four decades of experience covering the arts, entertainment, and culinary industries. A native of Chicago, she has a passion for the written world.