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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
Harshal Holkar Reviewed on :19 Feb 2026
Overall we had great experience with pickyourtrail! Right from bookings, itinerary and transfers everything went smoothly. Thank you team pickyourtrail!
Harshal Holkar Reviewed on :19 Feb 2026
Overall we had great experience with pickyourtrail! Right from bookings, itinerary and transfers everything went smoothly. Thank you team pickyourtrail!
Nandini Suresh Reviewed on :19 Feb 2026
We had booked our honeymoon trip via pick your trail. The trip was super smooth. Everything was very well organized and we are super satisfied. Special appreciation to fahim and jagatheeshpathy for helping us with the arrangement of trip and always helping us with the queries
Nandini Suresh Reviewed on :19 Feb 2026
We had booked our honeymoon trip via pick your trail. The trip was super smooth. Everything was very well organized and we are super satisfied. Special appreciation to fahim and jagatheeshpathy for helping us with the arrangement of trip and always helping us with the queries
Santhosh Kumar Reviewed on :18 Feb 2026
We recently completed a 7-day trip booked for thailand through PickYourTrail, and overall it was a great experience. The itinerary was well planned, hotels were comfortable, and airport transfers were smooth. Their support team was responsive whenever we had questions. The trip was mostly hassle-free and enjoyable. A few activities felt a little rushed, but overall everything was managed professionally. I would definitely recommend PickYourTrail for a well-organized and stress-free vacation.
Santhosh Kumar Reviewed on :18 Feb 2026
We recently completed a 7-day trip booked for thailand through PickYourTrail, and overall it was a great experience. The itinerary was well planned, hotels were comfortable, and airport transfers were smooth. Their support team was responsive whenever we had questions. The trip was mostly hassle-free and enjoyable. A few activities felt a little rushed, but overall everything was managed professionally. I would definitely recommend PickYourTrail for a well-organized and stress-free vacation.
Toolika Pandey Reviewed on :18 Feb 2026
It was great experience booking through pick your trail. They provided package at very reasonable rate as compared to other travel sources and the experience was good. We booked honeymoon package and they guided us everything regarding booking and the country that we travelled. Thanks a lot PYT!!!
Toolika Pandey Reviewed on :18 Feb 2026
It was great experience booking through pick your trail. They provided package at very reasonable rate as compared to other travel sources and the experience was good. We booked honeymoon package and they guided us everything regarding booking and the country that we travelled. Thanks a lot PYT!!!
Niwash Deen Reviewed on :18 Feb 2026
It was an wonderful experience for my family. Right from the start they guided me very well shabreen in phase 2 and Abinaya in phase 3. We enjoyed a lot, Thank you Pick Your Trail for your perfect itinerary and support.
Niwash Deen Reviewed on :18 Feb 2026
It was an wonderful experience for my family. Right from the start they guided me very well shabreen in phase 2 and Abinaya in phase 3. We enjoyed a lot, Thank you Pick Your Trail for your perfect itinerary and support.
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