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.

Budget

Hotel ratings

Thailand is now visa-free for Indian travellers - book your holiday now

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

Usa City Packages

New York Tour Packages₹173,337/Person

Las Vegas Tour Packages₹193,345/Person

Los Angeles Tour Packages₹193,345/Person

Boston Tour Packages₹287,759/Person

Orlando Tour Packages₹99,255/Person

Miami Tour Packages₹439,340/Person

San Francisco Tour Packages₹193,345/Person

Atlanta Tour Packages₹331,018/Person

Orlando Tour Packages₹99,255/Person

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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

Srinath Krishnaswamy

Reviewed on :20 Dec 2025

Help us to plan a 3-night stay trip to Maldives, with flexible options to choose from and constant follow up until end of the trip. Recommended !!

Srinath Krishnaswamy

Reviewed on :20 Dec 2025

Help us to plan a 3-night stay trip to Maldives, with flexible options to choose from and constant follow up until end of the trip. Recommended !!

Viji Paramasivam

Reviewed on :20 Dec 2025

We went to thailand and it was the best experience and pick your trail customized our trip as we needed. Thank you so much for providing us with such lovely experience.

Viji Paramasivam

Reviewed on :20 Dec 2025

We went to thailand and it was the best experience and pick your trail customized our trip as we needed. Thank you so much for providing us with such lovely experience.

Kedar Patkar

Reviewed on :20 Dec 2025

Good experience, awesome property & top notch services provided by all the stakeholders! Our Maldives trip to Sun Siyam World organized by Pickyourtrail was just impeccable perfect! - 10 on 10!! Very happy!