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4 days · 3 nights
Oct 7 - Oct 10, 2026
Moderate
0/6 booked
Group airport & activity transfers
Experience the vibrant culture of Chicago during Columbus Day Weekend – US Fall Getaway Cities (Top Picks) with this 4-day package. Enjoy a mix of cultural activities, event preparations, and post-event relaxation in the heart of Chicago.
This service is getting attention. Secure your spot now!
18+
Culture
USD 3,366.41 per person
Your experience via DALPS starts here
Arrival and Event Preparation
Arrive at O'Hare International Airport and transfer to your hotel in downtown Chicago.
Check into your 3-star comfortable hotel, Hotel Indigo Chicago Downtown, located near the event venue.
Take a leisurely stroll through Millennium Park, home to the famous Cloud Gate sculpture.
Enjoy a delicious dinner at The Purple Pig, known for its Mediterranean-inspired cuisine.
A comfortable 3-star hotel located in the heart of downtown Chicago, offering easy access to major attractions and event venues.
Stay: 3 night(s)
Columbus Day Weekend – US Fall Getaway Cities (Top Picks) Celebration
Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, famous for its pancakes and waffles.
Spend the morning exploring the Art Institute of Chicago, one of the oldest and largest art museums in the United States.
Enjoy a classic American lunch at Lou Mitchell's, a beloved Chicago institution.
Participate in the various cultural and celebratory events happening around the city for Columbus Day Weekend.
Post-Event Exploration
Start your day with a delicious breakfast at The Bongo Room, known for its eclectic menu.
Experience breathtaking views of the city from the Skydeck at Willis Tower.
Grab a classic Chicago hot dog for lunch at Portillo's, a local favorite.
Enjoy an Italian dinner at RPM Italian, known for its delicious pasta and wine selection.
Relaxation and Departure
Enjoy a relaxed breakfast at Standard Market, offering a variety of fresh and healthy options.
Spend the morning at the Lincoln Park Zoo, a beautiful and free zoo in the heart of the city.
Enjoy a leisurely lunch at Wildfire, known for its contemporary American cuisine.
Spend the afternoon shopping on Michigan Avenue, home to some of the city's best stores.
Transfer to O'Hare International Airport for your departure.
Everything you need for a seamless experience
3 nights accommodation at Hotel Indigo Chicago Downtown
Breakfast each morning
Dinner at The Purple Pig, Girl & The Goat, RPM Italian, and Wildfire
Entry to the Art Institute of Chicago and Skydeck Chicago
Transportation to and from O'Hare International Airport
Local transportation for all activities
Airfare to and from Chicago
Personal expenses and additional meals
Optional activities and experiences
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 4-day journey
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