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4 days · 3 nights
Sep 6 - Sep 9, 2026
Moderate
0/8 booked
Group airport & activity transfers
Dive into Chicago's extreme sports scene during Labor Day 2026 with this 4-day boutique hotel adventure, blending adrenaline-pumping activities and chic accommodations.
This service is getting attention. Secure your spot now!
18+
Extreme Sports
USD 2,483.29 per person
Your experience via DALPS starts here
Arrival & Downtown Exploration
Touch down at O'Hare International Airport and immerse yourself in the Windy City's vibrant energy.
Unwind at this stylish boutique hotel in the heart of River North, perfect for exploring Chicago's extreme sports scene.
A chic boutique hotel in River North, offering stylish rooms and a prime location for exploring Chicago's attractions.
Stay: 3 night(s)
Extreme Sports & Deep-Dish Delights
Experience the ultimate adrenaline rush with a tandem skydive over the picturesque Illinois countryside.
Enjoy a classic Chicago deep-dish pizza at this beloved pizzeria, known for its buttery crust and tangy sauce.
Labor Day Celebrations & Adventure
Join the city-wide celebrations with a vibrant parade and festive atmosphere, honoring workers and the spirit of Labor Day.
Rent a bike and explore the scenic Lakefront Trail, offering stunning views of Lake Michigan and the Chicago skyline.
Grab a classic Chicago-style hot dog at this iconic fast-food chain, famous for its flavorful toppings and convenient locations.
Final Adventures & Farewell
Test your limits at this state-of-the-art climbing gym, featuring a variety of climbing walls and bouldering areas.
Fuel up with a hearty brunch at this popular spot, known for its delicious pancakes and extensive menu.
Stroll through this iconic park, home to the famous Cloud Gate sculpture and beautiful gardens.
Bid farewell to the Windy City as you head to the airport for your departure.
Everything you need for a seamless experience
3 nights accommodation at The Hoxton, Chicago
Chicago Architecture River Cruise
Urban Adventure Quest
All activities and experiences as listed in the itinerary
Daily breakfast at the hotel
Provide tickets, entry to events or arranging collection for tickets for any ticketed events
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 8 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 4-day journey
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