Two Cities, Two Christmas Markets, One Magical USA Holiday
Chicago Christmas Magic
Experience the festive atmosphere of Chicago with a visit to the famous Christkindlmarket at Daley Plaza, surrounded by the city's seasonal lights and winter charm.
Downtown Chicago Stay
Enjoy three nights at 4★ Swissotel Chicago, ideally positioned for discovering Downtown Chicago, Millennium Park, The Bean and the Magnificent Mile.
Philadelphia Christmas Village
Discover the European-inspired Christmas Village at LOVE Park and City Hall, with festive stalls, seasonal shopping and a wonderful Christmas atmosphere.
Explore Historic Philadelphia
Spend time discovering Philadelphia's historic heart, including Old City, the Liberty Bell and Independence Hall, alongside the city's festive winter atmosphere.
“From Chicago's sparkling downtown to Philadelphia's festive Christmas Village, discover two iconic American cities at their most magical time of year.”
Experience the festive spirit of the USA with a seven-night journey combining the iconic cities of Chicago and Philadelphia. Discover the traditional charm of Chicago's Christkindlmarket at Daley Plaza, explore Philadelphia's European-inspired Christmas Village at LOVE Park and City Hall, and enjoy free time to experience the landmarks, shopping and winter atmosphere of two historic American cities.
Christmas in Chicago
Begin your festive USA escape in Chicago, staying for three nights at 4★ Swissotel Chicago. Set in the heart of Downtown Chicago, the hotel provides a convenient base for discovering the city's famous landmarks, shopping streets and seasonal attractions.
Chicago Christkindlmarket
Experience the festive atmosphere of Chicago's famous Christkindlmarket at Daley Plaza, with traditional Christmas stalls, seasonal gifts, food and drinks creating a memorable winter experience.
Downtown Chicago
Enjoy free time to explore Millennium Park, see The Bean and wander along the Magnificent Mile, with plenty of opportunities for festive shopping and discovering the city's winter atmosphere.
Swissotel Chicago
Stay three nights in a Classic Room at 4★ Swissotel Chicago on a Room Only basis, giving you the flexibility to experience Chicago's restaurants and festive dining options independently.
Christmas in Philadelphia
Continue your journey to Philadelphia for four nights at 4★ Hyatt Centric Rittenhouse Square Philadelphia. From its central location, enjoy easy access to the city's shopping, dining and historic attractions while experiencing the festive atmosphere of Center City.
Philadelphia Christmas Village
Explore the festive Christmas Village at LOVE Park and City Hall, where seasonal stalls, Christmas gifts, food and decorations create a European-inspired holiday atmosphere.
Historic Philadelphia
Spend time discovering Philadelphia's historic heart, including Old City, the Liberty Bell and Independence Hall, at your own pace.
Rittenhouse Square
Enjoy the lively atmosphere around Rittenhouse Square, with independent restaurants, cafés, boutiques and city sights close to your hotel.
Christmas Shopping
Make the most of your free time to browse festive markets, explore Center City's shops and discover seasonal gifts and local treats.
“From Chicago's sparkling downtown to Philadelphia's festive Christmas Village, discover two iconic American cities at their most enchanting time of year.”
Best Time to Visit Chicago & Philadelphia for Christmas
Late November and December are ideal for experiencing the festive side of Chicago and Philadelphia, when Christmas markets, seasonal decorations and winter events bring both cities to life.
For travellers looking specifically for Christmas market experiences, planning your visit during the official market dates provides the opportunity to enjoy the seasonal atmosphere, browse festive stalls and experience the cities at their most Christmassy.
Your Chicago & Philadelphia Christmas Escape
Travel from London on direct international flights with American Airlines and begin your seven-night USA Christmas adventure in Chicago. Stay three nights at 4★ Swissotel Chicago before flying onward to Philadelphia for four nights at 4★ Hyatt Centric Rittenhouse Square Philadelphia. With visits to two iconic Christmas markets, time to explore famous landmarks and plenty of opportunities for festive shopping, this itinerary brings together two distinctive American cities in one memorable winter holiday.
Explore More USA Holidays
Discover more USA holiday experiences with Perfect Holidays, from iconic city breaks and festive escapes to carefully planned multi-centre journeys.
Special Offer
Up to 40% Savings!
Book Your 2026 Christmas Market
Secure your stay with a minimum deposit from £199 pp
- ✓ Direct return international flights from London with American Airlines
- ✓ Domestic flight from Chicago to Philadelphia
- ✓ 3 nights stay at 4★ Swissotel Chicago
- ✓ Classic Room – Room Only
- ✓ 4 nights stay at 4★ Hyatt Centric Rittenhouse Square Philadelphia
- ✓ Standard Room – Room Only
Christmas Market Experiences
- ✓ Visit to Chicago Christkindlmarket at Daley Plaza
- ✓ Visit to Philadelphia Christmas Village at LOVE Park & City Hall
- ✓ Christmas shopping and festive leisure time in both cities
City Experiences
Chicago: Free time to explore Millennium Park, The Bean and Magnificent Mile.
Philadelphia: Free time to explore historic Old City, the Liberty Bell and Independence Hall.
Airport transfers, inter-hotel transfers, meals and optional guided excursions are not included unless specifically stated.
✓ ATOL Protected Holidays | ✓ ABTA Member | ✓ UK-Based Travel Experts
Chicago & Philadelphia Christmas Markets Itinerary
From your direct international flight from London to Chicago and onward journey to Philadelphia, this seven-night USA Christmas escape combines two iconic cities, two festive Christmas markets and plenty of time to discover the seasonal atmosphere, landmarks and shopping of each destination at your own pace.
London to Chicago
Depart London on your direct international flight with American Airlines to Chicago. On arrival, make your own way to 4★ Swissotel Chicago and check in to your Classic Room on a Room Only basis. The remainder of the day is free to settle in and begin discovering Downtown Chicago.
Chicago Christkindlmarket
Experience the festive atmosphere of Chicago's famous Christkindlmarket at Daley Plaza. Browse seasonal stalls, discover Christmas gifts and decorations, and enjoy the traditional festive atmosphere before exploring more of Downtown Chicago at your own pace.
Discover Downtown Chicago
Enjoy a full day to explore Chicago at your own pace. Visit Millennium Park and see The Bean, wander along the Magnificent Mile, discover the city's shops and restaurants, or return to the Christmas market for more festive shopping.
Chicago to Philadelphia
After checking out from Swissotel Chicago, make your own way to the airport for your included domestic flight to Philadelphia. On arrival, continue independently to 4★ Hyatt Centric Rittenhouse Square Philadelphia and check in to your Standard Room on a Room Only basis.
Philadelphia Christmas Village
Discover Philadelphia's festive Christmas Village at LOVE Park and City Hall. Explore the seasonal stalls, browse Christmas gifts and enjoy the European-inspired atmosphere before taking time to discover the surrounding Center City area.
Discover Historic Philadelphia
Spend the day exploring Philadelphia at your own pace. Discover the historic character of Old City, visit the Liberty Bell and see Independence Hall, while enjoying the festive atmosphere across the city.
Final Festive Day in Philadelphia
Enjoy your final full day in Philadelphia. Spend time around Rittenhouse Square, explore Center City's shops and restaurants, return to the Christmas Village or simply enjoy the city's festive winter atmosphere.
Philadelphia to London
After checking out from Hyatt Centric Rittenhouse Square Philadelphia, make your own way to Philadelphia International Airport for your direct return international flight with American Airlines to London, bringing your festive USA adventure to an end.
Seven nights across Chicago and Philadelphia, combining two iconic Christmas markets, central 4★ hotels, festive shopping and the freedom to explore two remarkable American cities at your own pace.
Chicago & Philadelphia Christmas Markets FAQs
Find answers to the most common questions about your Chicago and Philadelphia Christmas holiday, including flights, hotels, Christmas markets, room basis and travel between the two cities.
How many nights are included in this Christmas holiday?
This package includes 7 nights in total, with 3 nights in Chicago and 4 nights in Philadelphia.
Which hotels are included in the package?
The package includes 3 nights at 4★ Swissotel Chicago in a Classic Room and 4 nights at 4★ Hyatt Centric Rittenhouse Square Philadelphia in a Standard Room.
What meal plan is included at the hotels?
Both hotels are booked on a Room Only basis, so meals are not included in the package. This gives you the flexibility to enjoy Chicago and Philadelphia's wide choice of restaurants, cafés and festive dining options.
Are international flights included?
Yes. Direct return international flights from London with American Airlines are included in the package, subject to the selected travel dates and flight availability.
Is the flight from Chicago to Philadelphia included?
Yes. The domestic flight from Chicago to Philadelphia is included as part of the 7-night multi-city itinerary.
Are airport transfers included?
No. Airport transfers are not included in the package. Guests will make their own way between the airports and hotels.
Are transfers between the Chicago and Philadelphia hotels included?
No. The package includes the domestic flight from Chicago to Philadelphia, but airport and inter-hotel transfers are not included.
Are the Christmas markets included in the package?
Yes. The itinerary includes visits to Chicago Christkindlmarket at Daley Plaza and Philadelphia Christmas Village at LOVE Park & City Hall. General admission to these Christmas markets is free; guests pay separately for any purchases, food, drinks or optional activities.
Are guided city tours included?
No. Guided city tours and paid excursions are not included in the standard package. You can explore Chicago and Philadelphia independently or request optional excursions at an additional cost.
What can I explore in Chicago?
You can enjoy free time to discover Millennium Park, The Bean, the Magnificent Mile, Downtown Chicago and the Christkindlmarket at Daley Plaza.
What can I explore in Philadelphia?
Enjoy free time to explore Philadelphia's historic Old City, the Liberty Bell, Independence Hall, Rittenhouse Square, Center City and the Christmas Village.
When do the Christmas markets operate?
For 2026, Chicago Christkindlmarket at Daley Plaza is scheduled from 20 November to 24 December, while Philadelphia Christmas Village at LOVE Park & City Hall is scheduled from 21 November to 27 December. Market dates and opening hours are subject to change.
Can I do Christmas shopping during the holiday?
Yes. Both cities offer excellent opportunities for festive shopping, with the Christmas markets providing seasonal gifts, decorations and local products, alongside the wider shopping areas of Downtown Chicago and Center City Philadelphia.
Enjoy 7 nights across Chicago and Philadelphia with direct flights from London, 4★ hotels, an included domestic flight and visits to two iconic Christmas markets.
Special Offer
Up to 40% Savings!
Book Your 2026 Christmas Market
Secure your stay with a minimum deposit from £199 pp
- ✓ Direct return international flights from London with American Airlines
- ✓ Domestic flight from Chicago to Philadelphia
- ✓ 3 nights stay at 4★ Swissotel Chicago
- ✓ Classic Room – Room Only
- ✓ 4 nights stay at 4★ Hyatt Centric Rittenhouse Square Philadelphia
- ✓ Standard Room – Room Only
Christmas Market Experiences
- ✓ Visit to Chicago Christkindlmarket at Daley Plaza
- ✓ Visit to Philadelphia Christmas Village at LOVE Park & City Hall
- ✓ Christmas shopping and festive leisure time in both cities
City Experiences
Chicago: Free time to explore Millennium Park, The Bean and Magnificent Mile.
Philadelphia: Free time to explore historic Old City, the Liberty Bell and Independence Hall.
Airport transfers, inter-hotel transfers, meals and optional guided excursions are not included unless specifically stated.
✓ ATOL Protected Holidays | ✓ ABTA Member | ✓ UK-Based Travel Experts
