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5 days · 4 nights
Nov 23 - Nov 27, 2026
Moderate
0/6 booked
Group airport & activity transfers
Indulge in a luxurious 5-day shopping and nightlife adventure in Chicago, perfectly timed for the Thanksgiving Eve – Pre-Holiday Nightlife Cities (Top Picks) event on November 24, 2026. This package offers the ultimate blend of high-end shopping, vibrant nightlife, and luxurious accommodations, ensuring an unforgettable experience.
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18+
Shopping
USD 5,856.68 per person
Your experience via DALPS starts here
Arrival and Luxury Shopping
Arrive at O'Hare International Airport and transfer to your luxurious 5-star hotel in downtown Chicago.
Check into The Peninsula Chicago, a luxurious 5-star hotel known for its impeccable service and stunning views of the city.
Start your shopping adventure on the Magnificent Mile, home to high-end boutiques and flagship stores like Saks Fifth Avenue and Bloomingdale's.
Experience the epitome of luxury at The Peninsula Chicago, offering impeccable service, elegant rooms, and a prime location near the Magnificent Mile.
Stay: 4 night(s)
Thanksgiving Eve Nightlife Celebration
Spend the morning shopping at Water Tower Place, a premier shopping destination with a wide range of stores and dining options.
Enjoy a gourmet lunch at Café at The Peninsula, known for its exquisite pastries and delicious breakfast and lunch options.
Prepare for the Thanksgiving Eve – Pre-Holiday Nightlife Cities (Top Picks) event by visiting a nearby salon or spa for a makeover.
After the event, grab a late-night snack at Lou Mitchell's, a classic diner known for its hearty breakfast and all-day dining options.
Post-Event Relaxation and Shopping
Recover from the night before with a delicious brunch at Wildberry Pancakes and Café, known for its extensive pancake menu and cozy atmosphere.
Spend the day shopping at Oakbrook Center, one of the largest shopping malls in the Chicago area, featuring over 200 stores and dining options.
Take an evening stroll along the Chicago Riverwalk, enjoying the beautiful views of the city skyline and the calming waters of the river.
Cultural Exploration and Fine Dining
Start your day with a hearty breakfast at The Purple Pig, a popular spot known for its creative dishes and cozy atmosphere.
Spend the morning exploring the Art Institute of Chicago, one of the oldest and largest art museums in the United States.
Enjoy a light lunch at Café at The Peninsula, known for its exquisite pastries and delicious breakfast and lunch options.
Spend the afternoon shopping at The Shops at North Bridge, a premier shopping destination featuring high-end boutiques and flagship stores.
Final Shopping and Departure
Enjoy a final breakfast at The Purple Pig before heading out for your last shopping spree in Chicago.
Spend your last morning shopping on Michigan Avenue, home to a variety of high-end boutiques and flagship stores.
Enjoy a final lunch at Café at The Peninsula before checking out of your luxurious hotel.
Transfer to O'Hare International Airport for your departure, taking with you unforgettable memories of your Chicago adventure.
Everything you need for a seamless experience
4 nights accommodation at The Peninsula Chicago
Daily breakfast at the hotel
Reservations at top restaurants and nightclubs
Shopping excursions to premier shopping destinations
Transportation to and from O'Hare International Airport
Pre-event preparation services
Airfare to and from Chicago
Personal shopping expenses
Additional meals and drinks not specified in the itinerary
Optional activities and services not included in the itinerary
Everything you need to know about this service
Refunds for deposits: We will hold your spot as soon as you put down your deposit. However, if you decide to cancel your service, we will be unable to refund your deposit.
Refunds for balance payment: If you cancel your service on or before 1 month before the booking, you will get a refund of the remaining balance. This may or may not include the deposit amount. See deposit refund section above.
If you cancel your service after 1 month into the booking, no refunds will be issued.
Requests can be made for service changes only a month before the date.
Travelers are responsible for researching visa requirements and obtaining a visa if needed. Please check government websites to ensure you have the necessary documents, along with passport requirements, before your departure date. This includes necessary transit visas, permits, and vaccinations required prior to travel and any required reciprocity fees for the destination. DALPS will provide a booking confirmation document after purchase, which may be needed to obtain a visa.
If your visa is denied for any reason, DALPS will issue a refund based on the cancellation policy. However, we are unable to provide a refund after the cancellation due date has passed.
A full and valid passport is required for all persons traveling to any destination outside of one's home country. Most international services require a passport that's valid for at least six (6) months beyond the scheduled end of your service. DALPS will not issue refunds based on passport issues such as renewals or lost passports.
Passports should always be carried for entry into venues like clubs, bars etc.
Please check the inclusion and exclusion sections above. You'll find information about included meals, transfers, flights, and activities. If you have any questions or need support, please contact: support@dalps.org
This service has a moderate activity level. It includes various activities that require a reasonable level of fitness, as well as walking tours and site visits. Participants should be comfortable with walking for extended periods and managing some stairs and uneven terrain.
We recommend packing lightweight clothing, comfortable walking shoes, swimwear, a hat, sunscreen, insect repellent, a reusable water bottle, and appropriate clothing for site visits. Don't forget your camera to capture the beautiful landscapes!
Yes, group airport transfers are included both on arrival and departure. Please note that these are group transfers which may require waiting for other travelers. We will send you an email with recommended arrival and departure timeframes after you confirm your service.
This service has a maximum group size of 6 participants, ensuring an intimate and personalized experience. With a small group, you'll have more opportunities to connect with your guide and fellow travelers while enjoying a more flexible itinerary.
Join us on this unforgettable 5-day journey
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