Fuel up<\/strong><\/a><\/h2>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/24-Hour_Beatrix__ResizedImageWzEzMjAsODgxXQ.jpeg\")
<\/a><\/figure>\n\n\n\nSwing by Goddess and the Baker<\/a> for pastries, acai bowls, breakfast sandwiches, and more, or try the cafe at Venteux<\/a> for Parisian cafe fare with a contemporary twist. To try out what many say is the best breakfast sandwich in the Loop, stop in at Hero Coffee Bar<\/a>. Find more Loop cafes and bakeries here<\/a>.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/CafeVenteux_7.jpg\")
<\/a><\/figure>\n\n\n\nShop and see the sights<\/strong><\/h2>\n\n\n\nDowntown gets crowded fast during the holidays, so set aside some time in the morning for the chillest sightseeing experience. Have\u00a0a free, fun experience for the whole family at Mindworks<\/a>. Learn all about the science of human behavior, including the science of gift giving, gratitude, goal-setting, and much more. Plus, earn stocking stuffers like beanies, scarves, and books by participating in research studies.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/UChi_Mindworks_5922-1.jpg\")
<\/a><\/figure>\n\n\n\nStop by The Art Institute of Chicago<\/a> to snap a selfie with the wreathed lion statues<\/a> by the museum steps. Walk past Macy\u2019s<\/a> on State Street to enjoy the traditional holiday window displays<\/a>. While you\u2019re at it, head into the store\u2014and all the great State Street retailers<\/a>\u2014to knock out your holiday shopping before the crowds really hit!<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Art-Institute-Holiday-Wreathing-Lions-Chicago-IL-scaled.jpg\")
<\/a><\/figure>\n\n\n\nAFTERNOON<\/strong><\/h2>\n\n\n\nChristkindlmarket<\/strong><\/a><\/h2>\n\n\n\nOne of the most iconic downtown Chicago traditions of all is back this year after going virtual in 2020: Christkindlmarket<\/a>. Inspired by the 16th century Christkindlesmarkt in Nuremberg, Germany, one of the first outdoor markets of its kind, the Christkindlmarket is well-known for its vendors\u2019 high quality gifts and food, holiday cheer, and for being the ideal place for families to make unique memories.\u00a0<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Girl-Shopping-Looking-at-Ornaments-Christkindlmarket-2.jpg\")
<\/a><\/figure>\n\n\n\nIce skating<\/strong><\/h2>\n\n\n\nThere are two fantastic outdoor ice skating locations in the Loop, offering a little something for everyone. The Maggie Daley Park Ice Skating Ribbon<\/a> is a quarter-mile ribbon that offers incredible views of the city and an atmosphere of good old-fashioned fun for all ages. The ribbon is not a traditional oval rink, but rather a track that winds and slopes, offering a one-of-a-kind ice skating experience. The McCormick Tribune Ice Rink<\/a>, celebrating its 20th season, is a more traditional rink but also offers incredible skyline views. Nestled below Cloud Gate<\/a> (\u201cThe Bean\u201d), this is a picturesque experience you don\u2019t want to miss.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Winter-in-the-Loop-skating.jpg\")
<\/a><\/figure>\n\n\n\nStop for lunch<\/strong><\/a><\/h2>\n\n\n\nSwing by The Walnut Room<\/a> in Macy\u2019s<\/a> to dine under the Great Tree<\/a>, or stop in at The Berghoff<\/a> and you may just catch a glimpse of Santa! Whether you’re a kid (or just remained one at heart), spotting Santa in the Loop<\/a> is always a merry surprise.\u00a0<\/p>\n\n\n\nThere are a ton of great spots to eat lunch in the Loop, and you can find your options here<\/a>.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Macys-Tree_4-scaled.jpg\")
<\/a><\/figure>\n\n\n\nEVENING<\/strong><\/h2>\n\n\n\nHoliday theatre in the Loop<\/strong><\/h2>\n\n\n\nThe Loop’s Theatre District is overflowing with amazing shows this holiday season. Ballet 5:8’s Beyond the Nutcracker<\/a> is coming to Chicago! Join this magical trip around the world to discover the true beauty of Christmas. Performances begin November 17 with Christkindlmarket<\/a> performances in Daley Plaza. For all the young ballerinas, Museum 21C Chicago will be hosting Beyond the Nutcracker Books and Ballerinas on November 18. The full production goes onstage November 25 and 26 at the Athenaeum Theater in Chicago and continues December 16 and 17 at Lincoln Way East in Frankfort, IL. More information and tickets at Ballet58.org<\/a><\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/B58-Beyond-the-Nutcracker-1__ResizedImageWzEzMjAsNzQzXQ.png\")
<\/a><\/figure>\n\n\n\nCheck out Boop! The Musical<\/a> <\/a>at CIBC Theatre, A Christmas Carol<\/em><\/a> at Goodman Theatre<\/a>, Home Alone<\/em> in Concert<\/a> with the Chicago Symphony Orchestra<\/a>, \u2018Twas the Night Before\u2026<\/em><\/a> by Cirque du Soleil at the Chicago Theatre<\/a>, The Joffrey Ballet\u2019s The Nutcracker<\/em><\/a> at Lyric Opera House, Purchase theatre tickets from Hot Tix<\/a> in advance to see holiday theatre at the best rates. Tickets are available at half-price at HotTix.org<\/a>, or you can stop by their two Loop locations, 108 N. State\u00a0at Guest Services inside of Block 37<\/a> or 72 E. Randolph.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/nutcrackerjoffrey-v2__ResizedImageWzEzMjAsNzQzXQ.jpeg\")
<\/a><\/figure>\n\n\n\nArt on theMART<\/strong><\/a><\/h2>\n\n\n\nDon\u2019t miss this larger-than-life experience: an artistic interpretation of The Joffrey Ballet\u2019s The Nutcracker<\/em><\/a> projected onto the Merchandise Mart\u2019s 2.5-acre river-facade. Art on theMART is the largest permanent digital art projection in the world, right here along the iconic Chicago River. The projection can be viewed for free nightly at 7 and 7:30 p.m.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Nutcracker-Art-on-theMart.jpg\")
<\/a><\/figure>\n\n\n\nAll of the lights<\/strong><\/h2>\n\n\n\nThe Chicago Loop is always a lit-up wonderland, but especially so during the holidays. Feel the magic of the merry season as you stroll along the State Street holiday lights<\/a>.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/courtesy-of-Chicago-Loop-Alliance-01-v3__ResizedImageWzEzMjAsODgwXQ.jpg\")
<\/figure>\n\n\n\nHead over to Millennium Park<\/a> to witness the City of Chicago\u2019s 108th Christmas Tree<\/a>, or head north of the Loop to the Magnificent Mile for their annual Lights Festival<\/a>.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Christmas-Tree-in-Millenium-Park-Chicago-Loop-scaled.jpg\")
<\/a><\/figure>\n\n\n\nSTAY THE NIGHT<\/strong><\/a><\/h2>\n\n\n\nThe Blackstone Hotel<\/a><\/h2>\n\n\n\nThis holiday season, create a new tradition with your loved ones and join The Blackstone Hotel<\/a> for an unforgettable Presidential experience with this immersive luxury package.\u00a0Complete with historical accents that transport you to the captivating 1960\u2019s Kennedy Christmas, The Blackstone\u2019s “A Kennedy Christmas” package welcomes families and travelers to indulge in a magically timeless holiday scene. Their famous Presidential Suite will become an immersive ode to the lavish 1960s Kennedy White House, embellished with a twinkling tree, marching nutcrackers and presidential details such as a letter typing station and cozy White House blanket.\u00a0<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Kennedy-Hot-Cocoa.jpg\")
<\/a><\/figure>\n\n\n\nThe Palmer House Hilton\u00a0<\/strong><\/a><\/h2>\n\n\n\nThe Palmer House Hilton<\/a> has been hosting visitors to the Chicago Loop for 150 years. It is America\u2019s longest-operating hotel and offers guests the ultimate experience in luxury from the moment they arrive, with a two-story, gilded lobby with a formal staircase, marble-topped tables, velvet seating, and a ceiling mural depicting Greek mythology. It\u2019s a Loop icon, and a wonderful place to end your long day celebrating the holidays in the Loop.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Palmer-House-Hilton-Hotel-Chicago-Loop.jpg\")
<\/a><\/figure>\n\n\n\nKimpton Gray<\/strong><\/a><\/h2>\n\n\n\nIn the center of the Chicago Loop, the Kimpton Gray<\/a> is located close to several holiday festivities and winter activities. Between Vol. 39 and Boleo<\/a>, there\u2019s nowhere better to enjoy a nightcap and then head to bed.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/Kimpton-Gray-holiday-lobby.jpg\")
<\/a><\/figure>\n\n\n\ntheWit Hotel<\/strong><\/a><\/h2>\n\n\n\nBoldly living in the heart of Chicago\u2019s theater, arts, and shopping district, theWit Hotel<\/a> is the perfect spot to end your 24-hour holiday extravaganza. Stop by the 27th floor to enjoy one last drink or snack at ROOF on theWit<\/a>, with unbeatable views of festive State Street, and then head up to your hip, modern room designed to celebrate creativity and expression.<\/p>\n\n\n\n![\"\"\/](\"https:\/\/loopchicago.com\/wp-content\/uploads\/2026\/05\/theWit202-1.jpg\")
<\/a><\/figure>\n\n\n\n
<\/a><\/figure>\n\n\n\nSwing by Goddess and the Baker<\/a> for pastries, acai bowls, breakfast sandwiches, and more, or try the cafe at Venteux<\/a> for Parisian cafe fare with a contemporary twist. To try out what many say is the best breakfast sandwich in the Loop, stop in at Hero Coffee Bar<\/a>. Find more Loop cafes and bakeries here<\/a>.<\/p>\n\n\n\n Downtown gets crowded fast during the holidays, so set aside some time in the morning for the chillest sightseeing experience. Have\u00a0a free, fun experience for the whole family at Mindworks<\/a>. Learn all about the science of human behavior, including the science of gift giving, gratitude, goal-setting, and much more. Plus, earn stocking stuffers like beanies, scarves, and books by participating in research studies.<\/p>\n\n\n\n Stop by The Art Institute of Chicago<\/a> to snap a selfie with the wreathed lion statues<\/a> by the museum steps. Walk past Macy\u2019s<\/a> on State Street to enjoy the traditional holiday window displays<\/a>. While you\u2019re at it, head into the store\u2014and all the great State Street retailers<\/a>\u2014to knock out your holiday shopping before the crowds really hit!<\/p>\n\n\n\n One of the most iconic downtown Chicago traditions of all is back this year after going virtual in 2020: Christkindlmarket<\/a>. Inspired by the 16th century Christkindlesmarkt in Nuremberg, Germany, one of the first outdoor markets of its kind, the Christkindlmarket is well-known for its vendors\u2019 high quality gifts and food, holiday cheer, and for being the ideal place for families to make unique memories.\u00a0<\/p>\n\n\n\n There are two fantastic outdoor ice skating locations in the Loop, offering a little something for everyone. The Maggie Daley Park Ice Skating Ribbon<\/a> is a quarter-mile ribbon that offers incredible views of the city and an atmosphere of good old-fashioned fun for all ages. The ribbon is not a traditional oval rink, but rather a track that winds and slopes, offering a one-of-a-kind ice skating experience. The McCormick Tribune Ice Rink<\/a>, celebrating its 20th season, is a more traditional rink but also offers incredible skyline views. Nestled below Cloud Gate<\/a> (\u201cThe Bean\u201d), this is a picturesque experience you don\u2019t want to miss.<\/p>\n\n\n\n Swing by The Walnut Room<\/a> in Macy\u2019s<\/a> to dine under the Great Tree<\/a>, or stop in at The Berghoff<\/a> and you may just catch a glimpse of Santa! Whether you’re a kid (or just remained one at heart), spotting Santa in the Loop<\/a> is always a merry surprise.\u00a0<\/p>\n\n\n\n There are a ton of great spots to eat lunch in the Loop, and you can find your options here<\/a>.<\/p>\n\n\n\n The Loop’s Theatre District is overflowing with amazing shows this holiday season. Ballet 5:8’s Beyond the Nutcracker<\/a> is coming to Chicago! Join this magical trip around the world to discover the true beauty of Christmas. Performances begin November 17 with Christkindlmarket<\/a> performances in Daley Plaza. For all the young ballerinas, Museum 21C Chicago will be hosting Beyond the Nutcracker Books and Ballerinas on November 18. The full production goes onstage November 25 and 26 at the Athenaeum Theater in Chicago and continues December 16 and 17 at Lincoln Way East in Frankfort, IL. More information and tickets at Ballet58.org<\/a><\/p>\n\n\n\n Check out Boop! The Musical<\/a> <\/a>at CIBC Theatre, A Christmas Carol<\/em><\/a> at Goodman Theatre<\/a>, Home Alone<\/em> in Concert<\/a> with the Chicago Symphony Orchestra<\/a>, \u2018Twas the Night Before\u2026<\/em><\/a> by Cirque du Soleil at the Chicago Theatre<\/a>, The Joffrey Ballet\u2019s The Nutcracker<\/em><\/a> at Lyric Opera House, Purchase theatre tickets from Hot Tix<\/a> in advance to see holiday theatre at the best rates. Tickets are available at half-price at HotTix.org<\/a>, or you can stop by their two Loop locations, 108 N. State\u00a0at Guest Services inside of Block 37<\/a> or 72 E. Randolph.<\/p>\n\n\n\n Don\u2019t miss this larger-than-life experience: an artistic interpretation of The Joffrey Ballet\u2019s The Nutcracker<\/em><\/a> projected onto the Merchandise Mart\u2019s 2.5-acre river-facade. Art on theMART is the largest permanent digital art projection in the world, right here along the iconic Chicago River. The projection can be viewed for free nightly at 7 and 7:30 p.m.<\/p>\n\n\n\n The Chicago Loop is always a lit-up wonderland, but especially so during the holidays. Feel the magic of the merry season as you stroll along the State Street holiday lights<\/a>.<\/p>\n\n\n\n Head over to Millennium Park<\/a> to witness the City of Chicago\u2019s 108th Christmas Tree<\/a>, or head north of the Loop to the Magnificent Mile for their annual Lights Festival<\/a>.<\/p>\n\n\n\n This holiday season, create a new tradition with your loved ones and join The Blackstone Hotel<\/a> for an unforgettable Presidential experience with this immersive luxury package.\u00a0Complete with historical accents that transport you to the captivating 1960\u2019s Kennedy Christmas, The Blackstone\u2019s “A Kennedy Christmas” package welcomes families and travelers to indulge in a magically timeless holiday scene. Their famous Presidential Suite will become an immersive ode to the lavish 1960s Kennedy White House, embellished with a twinkling tree, marching nutcrackers and presidential details such as a letter typing station and cozy White House blanket.\u00a0<\/p>\n\n\n\n The Palmer House Hilton<\/a> has been hosting visitors to the Chicago Loop for 150 years. It is America\u2019s longest-operating hotel and offers guests the ultimate experience in luxury from the moment they arrive, with a two-story, gilded lobby with a formal staircase, marble-topped tables, velvet seating, and a ceiling mural depicting Greek mythology. It\u2019s a Loop icon, and a wonderful place to end your long day celebrating the holidays in the Loop.<\/p>\n\n\n\n In the center of the Chicago Loop, the Kimpton Gray<\/a> is located close to several holiday festivities and winter activities. Between Vol. 39 and Boleo<\/a>, there\u2019s nowhere better to enjoy a nightcap and then head to bed.<\/p>\n\n\n\n Boldly living in the heart of Chicago\u2019s theater, arts, and shopping district, theWit Hotel<\/a> is the perfect spot to end your 24-hour holiday extravaganza. Stop by the 27th floor to enjoy one last drink or snack at ROOF on theWit<\/a>, with unbeatable views of festive State Street, and then head up to your hip, modern room designed to celebrate creativity and expression.<\/p>\n\n\n\n<\/a><\/figure>\n\n\n\nShop and see the sights<\/strong><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\n<\/a><\/figure>\n\n\n\nAFTERNOON<\/strong><\/h2>\n\n\n\n
Christkindlmarket<\/strong><\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\nIce skating<\/strong><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\nStop for lunch<\/strong><\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\nEVENING<\/strong><\/h2>\n\n\n\n
Holiday theatre in the Loop<\/strong><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\n<\/a><\/figure>\n\n\n\nArt on theMART<\/strong><\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\nAll of the lights<\/strong><\/h2>\n\n\n\n
<\/figure>\n\n\n\n<\/a><\/figure>\n\n\n\nSTAY THE NIGHT<\/strong><\/a><\/h2>\n\n\n\n
The Blackstone Hotel<\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\nThe Palmer House Hilton\u00a0<\/strong><\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\nKimpton Gray<\/strong><\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\ntheWit Hotel<\/strong><\/a><\/h2>\n\n\n\n
<\/a><\/figure>\n\n\n\n