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IDEAL DURATION4 nights
STARTING PRICE₹231,583
OUR EXPERTISE
Chicago Tour Packages
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
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
Hotels8 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
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
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
Meghraj Singh Reviewed on :11 Mar 2026
It was a nice facilities and coordination
Meghraj Singh Reviewed on :11 Mar 2026
It was a nice facilities and coordination
Prakash Peksi Reviewed on :11 Mar 2026
Well managed and seem less of execution
Prakash Peksi Reviewed on :11 Mar 2026
Well managed and seem less of execution
Soumya Devi Reviewed on :10 Mar 2026
Had wonderful and stress-free experience with pick your trail.
Soumya Devi Reviewed on :10 Mar 2026
Had wonderful and stress-free experience with pick your trail.
Mehul Gandhi Reviewed on :10 Mar 2026
I had my Maldives booking done from pickyourtrail app and believe me that I had a very good experience. Their representatives were in constant touch and very ready to solve my queries immediately. Highly recommend
Mehul Gandhi Reviewed on :10 Mar 2026
I had my Maldives booking done from pickyourtrail app and believe me that I had a very good experience. Their representatives were in constant touch and very ready to solve my queries immediately. Highly recommend
Aditya Arun Reviewed on :09 Mar 2026
8.5 We liked : 1. Well organised trip with absolute no stress during Travel. 2. Time to Time pickup and drop, additionally drivers were pretty good and of welcoming nature. 3. Food and service were really tasty in both the Hotels. 4. All pre-visit information and requested modifications were delivered amazingly. Improvement : 1. hotel room details (backside room, no good view from window, and missing gallery) 2. Swimming pool not present in IBIS hotel. (Same missing view/gallery) 3. Better cruise experience expected, food was bland and no open-upper deck. (We saw a few cruises there with an open upper deck) Improvements are just suggestions and not complaints.
Aditya Arun Reviewed on :09 Mar 2026
8.5 We liked : 1. Well organised trip with absolute no stress during Travel. 2. Time to Time pickup and drop, additionally drivers were pretty good and of welcoming nature. 3. Food and service were really tasty in both the Hotels. 4. All pre-visit information and requested modifications were delivered amazingly. Improvement : 1. hotel room details (backside room, no good view from window, and missing gallery) 2. Swimming pool not present in IBIS hotel. (Same missing view/gallery) 3. Better cruise experience expected, food was bland and no open-upper deck. (We saw a few cruises there with an open upper deck) Improvements are just suggestions and not complaints.
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