
Chicago, with its numerous holiday happenings and millions of holiday lights, is a magical destination. Wondering where to stay and what to do? Here are some ideas for you.
Gather at the Four Seasons Hotel Chicago this Thanksgiving (Thursday, November 27, 12:00PM – 6:00PM) for Adorn Bar & Restaurant’s heartwarming Thanksgiving Grand Feast Experience. Celebrate the season in style with an abundant spread of gourmet stations, decadent dishes, and irresistible sweets. Whether you’re making new memories or honoring cherished traditions, Adorn invites you to savor every bite—and every moment—with warmth, joy, and festive flavor.

Savor the season with a playful twist on a timeless tradition. Delight in an elegant afternoon of festive indulgence at the Teddy Bear Tea, featuring artfully crafted tea sandwiches, exquisite desserts, and a thoughtfully curated selection of fine teas. Toast the occasion at our sparkling mimosa station, while little ones are enchanted by whimsical holiday entertainment and receive a charming teddy bear keepsake to treasure.
- Saturdays and Sundays, November 29 & 30, December 7, 13*, 20, 27 & 28
- 1st Seating: 10:00 AM; 2nd Seating: 1:00 PM; *10 AM Seating Only
- $185 per adult / $65 per child (6-12 years old)
- Children 5 and under are complimentary

Treat your loved ones to an unforgettable Christmas Day Feast at Four Seasons Hotel Chicago (Thursday, December 25,12:00PM – 6:00PM) . Delight in festive fare from chef-attended action stations and an elaborate chocolate buffet, while little ones enjoy holiday-themed activities designed just for them. A live band sets the scene with cheerful sounds of the season, and our decadent hot chocolate station—complete with a “Spike Your Cocoa” option—adds a playful, grown-up twist. A memorable experience for guests of all ages, wrapped in the magic of the holidays.
- $285 per adult / $95 per child (6-12 years old), Adult pricing includes one glass of champagne (Pricing is exclusive of Tax & Gratuity)

Ring in the New Year with an opulent New Year’s Eve Dinner at Adorn (Wednesday, December 31, seatings at 7:00PM and 9:00PM). Indulge in a luxurious five-course journey. Savor every moment with decadent canapés, artfully prepared appetizers, and a choice of exquisite entrée, culminating in a show-stopping dessert.
- $225 Per Person exclusive of tax and gratuity

the Albert, the Italian-American restaurant located at the luxury boutique Hotel EMC2, Autograph Collection, welcomes the festive season with an exciting lineup of dining experiences. Under the direction of acclaimed Chef Steve Chiappetti, the Albert’s menus and events honor his Calabrian heritage while embracing Chicago’s culinary vibrancy. Guests can look forward to special offerings, holiday feasts, a charitable book drive, an early New Year’s Eve party, and interactive wine and cocktail classes — all designed to joyfully gather loved ones around the table.
- Thanksgiving Chef Hotline – Wednesday, November 26, 2025 | 11 a.m. to 5 p.m.
Turkey emergency? Stuffing disaster? Chef Chiappetti is back in 2025 and just a phone call away with The Albert’s Thanksgiving Chef Hotline. From troubleshooting to expert tips, Chicagoans can count on his culinary guidance to present their holiday meals without breaking a sweat! Call 1-833-THX-CHEF (1-833-849-2433).
- Holiday Book Drive: Share a Story, Light the Season – November 19-December 31, 2025

Hotel EMC2 invites guests to celebrate the spirit of giving through Share a Story, Light the Season in partnership with Books4Cause, a Chicago-based social venture dedicated to expanding access to books and education worldwide. From November 18 through December 31, guests who bring a gently used book to donate at the Albert, will receive a complimentary glass of wine in return. Guests are invited to place their books beneath the hotel’s striking holiday tree while enjoying canapés, cocktails, and the warmth of the season. Each book donated supports Books4Cause’s mission to recirculate books into the hands of new readers, helping to build libraries and empower communities both locally and abroad. At Hotel EMC2, where art and science live in harmony, the initiative is a reflection of the property’s belief that curiosity, creativity, and compassion are all part of a story worth sharing. 21+. Limit one per guest, per visit. Available during service hours only.
- Thanksgiving All-Day Buffet – Thursday, November 27, 2025 | 11:30 a.m. to 8 p.m.
$65 per person (excludes beverages, tax, and gratuity)
Give thanks with Chef Chiappetti’s festive buffet featuring roasted turkey with cranberry stuffing, honey glazed ham, cheese tortellini, Sicilian mushrooms, shaved salumi and Italian cheeses, roasted vegetables, Italian frittata, and tables laden with housemade pies and other sweet treats.
- Christmas Eve Dinner

Wednesday, December 24, 2025 – 5 p.m. to close
$60 per person, including a glass of rosé prosecco (excludes additional beverages, tax, and gratuity)
Let the night before Christmas be a decadent culinary occasion with a pre-fix menu featuring:
- Choice of Crostini: Prosciutto, ricotta, and honey, or Confit chicken, pesto, and ricotta, or Sicilian mushroom, ricotta, and chili
- Main Course: Lobster ravioli, roasted red pepper sauce, or Beef Wellington, or Dover Sole, shrimp soufflé
- Dessert: Nonna’s Tiramisu
- Christmas Day Buffet
Thursday, December 25, 2025 – 11:30 a.m.
$70 per person with a glass of Champagne (excludes other beverages, tax and gratuity)
Wake up and feast on a bountiful buffet and special menu selections featuring both Italian and classic American dishes. Guests can tour the antipasti buffet, choose their entree and then cap off the celebration with sweets upon sweets at the 20-foot dessert table.
- Antipasti Buffet: Roasted mint carrots, Sicilian mushrooms, asparagus with aged balsamic, Italian olives, Shaved salumi, Italian cheeses, fig jam, crackers, nuts, Frittata, spiral ham, cheese tortellini with fresh basil tomato sauce and more.
- Entree Selections: Eggs Benedict, Lemon Ricotta Pancakes, Roasted Turkey, Herb Crusted Prime Ribeye, Gnocchi, Seared Pacific Coast Salmon, Grilled Lamb Chops
- The 20-Foot Dessert Buffet: Assorted Cakes, Pies, Cannoli, Dark Chocolate Brownies, Butter Cookies, and more

- Rockin’ Italian Style New Year’s Celebration
Wednesday, December 31, 2025 | 4 to 7 p.m.
$55 per person (excludes tax and gratuity)
For those who wish to celebrate early and watch the ball drop at home, all are invited to enjoy live music as the clock strikes midnight in Italy. They will have the chance to honor the grape-eating tradition that accompanies the holiday in Italy, all while delighting in a beverage bar featuring rosé prosecco and espresso martinis and a Sicilian pizza bar including favorites like potato, rosemary, goat cheese, duck prosciutto, pinenuts, mushroom, provolone, soprasata, sweet peppers, pesto, four cheese, and white truffle cream. A homemade pasta bar will dole out the traditional Casarece pasta with shrimp, spinach and lobster cream sauce. Unlimited servings of Nonna’s Tiramisu will start the New Year on a high note!
- New Year’s Eve Dinner
Wednesday, December 31, 2025 | 5 p.m. to close
$90 per person
End the year with an extraordinary prix fixe tasting menu featuring:
- 1st Course: Smoked Duck Consommé and black truffle puff crust, or Hamachi crudo, black garlic, and tomato jus
- 2nd Course: Choice Of Risotto with shrimp, saffron broth and peas, or Garginelle with lamb sausage and fennel dust
- 3rd Course: Choice Of Roasted rack of lamb stuffed with pesto, or Snapper, fresh crab crust, and prosecco sauce
- 4th Course: Chocolate Decadence

Staypineapple The Loop is offering the following meal packages:
- Holiday Tea at Atwood – Available November 1, 2025 through January 10, 2026, Atwood will offer a festive Holiday Tea menu with a selection of aromatic teas, savory sandwiches and decadent sweets, available daily from 11 AM-5 PM by reservation, $55 per person. (Menu and photos)

- Atwood’s Theatre Prix Fixe – To celebrate the fall and winter theatre season, starting October 1, 2026, Atwood, located in the heart of the theatre district, is offering a prix fixe menu, perfect for pre- or post-show dining. The three courses feature seasonal flavors in main dishes such as Pumpkin Risotto, Pork Shoulder Ragout and Pan-Roasted Chicken. Available daily 11 AM-9 PM, no reservation required, $52 per person.(Menu and photos)

The Pendry Chicago’s special holiday events include:
- Holiday Lights & Festive Kick-Off: Festival of Lights Champagne & Hot Chocolate Toast (Nov. 22 | 4 – 5:30 pm | Lobby) – Celebration of Chicago’s official holiday season kick-off with champagne and hot chocolate before the lighting ceremony.
- Letters to Santa (Nov. 22 – Dec. 25 | 10 am – 7 pm) in Lobby – Kids can visit the Concierge to write their letter to Santa and send it to the North Pole.
- Myles Hayes Holiday Music (Nov. 22 – Dec. 31 | Saturdays, 4 – 6 pm) at Bar Pendry – Live holiday-inspired performances by Chicago Jazz artist Myles Hayes.

- Festive Boozy Tea (Dec. 7 – Dec. 28 | Sundays, 11 am – 3 pm) at Bar Pendry – Bar Pendry puts a festive spin on Sunday afternoon tea with Festive Boozy Tea, pairing tea-based cocktails with a three-tiered tower of sweet and savory bites accompanied by live music from Chicago musicians. Guests can enjoy holiday delicacies such as Lobster Quiche with Parmesan Royale and Black Truffle and Gingerbread Profiteroles with White Russian Crème. $100 per person inclusive of tax & gratuity. View menu here.
For more information about where to stay and what to do in the city, visit Choose Chicago.






































