Let’s enrich ourselves in Chicago and explore its landmarks and cultural life with one of the luxurious Chicago holiday packages available on PickYourTrail. Through this package, tourists can visit some of the most famous attractions, such as Willis Tower, Millennium Park, and the Art Institute of Chicago.

Chicago could hardly be enumerated among the sights themselves, but it's worth mentioning its specialties like deep-dish pizza, jazz, and the lakefront. As one of the biggest cities in the United States, Chicago offers many things, from the best museums to amazing culinary experiences. All of it can be booked with the PickYourTrail Chicago luxury holiday package. Plan your wanderlust at PickYourTrail and explore more of the Windy City with our Chicago tour package.

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Hotel ratings

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Incredible 14 day USA itinerary for the Solo travellers

13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5

Hotels

8 activities

Shared transfer

24x7 concierge

₹231,582

13 nights / person

360 Chicago Observation Deck (formerly John Hancock Observatory) Admission

+ 7 more

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Reviews from Usa travellers

Arpana Devarhubli

Reviewed on :07 Oct 2024

Just completed a trip to Alaska for the Northern Lights!! It was Amazing!! Pre journey readiness is awesome with Pickyourtrail, they ensured the itinerary was as per what we wanted and nothing more or less. The during journey follow ups and touch points made us feel secure and connected. We are definitely going to them for our next one

Arpana Devarhubli

Reviewed on :07 Oct 2024

Nikhil Kumar

Reviewed on :29 Jan 2026

Great experience overall! The platform is very user-friendly, with plenty of options across destinations, hotels, and activities. Prices were competitive, and the booking process was smooth and quick. I especially liked the clear filters and detailed reviews, which made choosing the right stay easy. Customer support was responsive and helpful when I had a small query. Would definitely use this platform again for future vacations.

Nikhil Kumar

Reviewed on :29 Jan 2026

Binita Negi

Reviewed on :29 Jan 2026

We booked a customized Bali package through Pickyourtrail, and the entire experience was truly wonderful. The itinerary was well planned as per our familys preferences, which made the trip smooth and stress-free. The ground staff in Bali was awesomevery supportive, polite, and always available whenever we needed help. Because of their excellent coordination, my family and I were able to enjoy the trip to the fullest. Overall, it was a memorable experience, and we really liked the way everything was managed. Highly recommended!

Binita Negi

Reviewed on :29 Jan 2026

Apurva Rathod

Reviewed on :29 Jan 2026

It was great trip arrange by pick up trail

Apurva Rathod

Reviewed on :29 Jan 2026

It was great trip arrange by pick up trail

Jamuna Shanmugam

Reviewed on :28 Jan 2026

Recently booked a Bali trip through PYT, and it turned out to be a truly wonderful experience. Meghana did an excellent job during the planning phase as she patiently accommodated all my requests and shared thoughtful, spot-on suggestions. Once we landed, Shreya was always available for urgent queries and ensured smooth coordination throughout the trip. Everything was handled seamlessly. A special shout-out to our Bali driver, Slamat, whose guidance and local insights made the journey even more memorable. Overall, a well-planned, stress-free, and delightful experience. Thanks to Meghana, Shreya, and the entire PYT team!