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Highlights
- Day 1: Fly to IllinoisUpon arriving in Chicago, we settle in for the next four nights. Enjoy the convenience of unpacking only once at a centrally located hotel on The Magnificent Mile, perfect for visiting nearby attractions, shopping, and dining.
- Day 2: City Tour & ChristkindlmarketWake up to an included breakfast each morning! Our adventure begins with sightseeing in the Windy City. A local guide boards our motorcoach to share the fascinating history behind Chicago’s most iconic areas, such as Millennium Park with its famous Christmas tree. Next, we get to know fellow travelers over an elegant Welcome Lunch at The Walnut Room in Macy’s, the first restaurant ever opened in a department store. We then take a short stroll to Christkindlmarket at Daley Plaza, ranked one of the best Christmas markets in the world, to discover festive cheer among international and local vendors. Don’t miss an opportunity to taste German beverages, like mulled wine! Afterwards, enjoy time at leisure along The Magnificent Mile to see historic buildings glimmering with holiday magic. Free time continues this evening at Navy Pier, where the spirit of the season comes alive at “Light Up The Lake,” the largest indoor and outdoor holiday experience in Chicago. Soak up views of the glistening lake, walk among dazzling light displays, watch live entertainment, and more.
Meals Included: Breakfast, Lunch
- Day 3: Holiday Traditions & Broadway LightsThis morning, we’re immersed in holiday traditions from around the globe at the Museum of Science and Industry’s Christmas Around the World and Holidays of Light exhibits. Browse incredible displays while learning how different cultures celebrate this time of year, then enjoy time to see other award-winning exhibits and grab a bite to eat. Afterwards, find your adventurous side during a quintessential Chicago experience – stepping out onto The Ledge of Willis Tower’s Skydeck for unrivaled views of the cityscape. Following dinner on your own, we venture into the Theatre District for a spectacular Broadway show of a holiday classic featuring impressive decor, timeless music, and talented performers.
Meals Included: Breakfast
- Day 4: Chicago at LeisureToday is yours to explore as you wish! Great options include seeing another Broadway show, visiting one of the many museums, strolling the Riverwalk, feeling an adrenaline rush at 360 Chicago in the John Hancock Building, ice skating at Navy Pier, or shopping for souvenirs. Later, we gather to celebrate our travel memories with a Farewell Dinner at a local restaurant. Our evening concludes at Lincoln Park Zoo’s vibrant ZooLights event featuring luminous displays, holiday season activities, music, and of course, festive animal exhibits.
Meals Included: Breakfast, Dinner
- Day 5: Fly HomeWe return home today with wonderful memories of our time in Chicago’s winter wonderland.
Meals Included: Breakfast
Dec 6-10, 2026
$4,299
per person
$3,599
per person
Sep 22, 2026
What's Included
All Accommodations
- 4 nights at The Westin Michigan Avenue Chicago
Attractions & Highlights
- Chicago guided city tour
- Christkindlmarket at Daley Plaza
- Navy Pier
- The Magnificent Mile
- Broadway In Chicago performance
- Museum of Science & Industry feat. Christmas Around the World & Holidays of Light exhibits
- Skydeck Chicago at Willis Tower
- Time at leisure
- ZooLights at Lincoln Park Zoo
6 Excellent Meals
- Daily breakfast
- Welcome Lunch at The Walnut Room
- Farewell Dinner in Chicago
Learn more about what's included with the Holiday Advantage.
Birmingham - Birmingham-Shuttlesworth International Airport




