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IDEAL DURATION4 nights
STARTING PRICEAED 231,583
OUR EXPERTISE
Chicago Holiday Packages from UAE
Embark on an unforgettable journey to Chicago, where breathtaking landscapes, vibrant culture, and rich history await you. Whether you’re exploring iconic landmarks, indulging in local cuisine, or unwinding in luxury resorts, Chicago offers a diverse experience for every traveler. From the bustling streets of its cities to tranquil escapes in nature, this destination promises something for everyone. Get ready to immerse yourself in the unique beauty and charm of Chicago, a place that blends tradition with modernity in the most captivating way.
Why Book with Pickyourtrail?
Planning a trip can be overwhelming, but with the right travel partner, your dream Chicago vacation can be seamless and hassle-free. That’s where Pickyourtrail comes in. Crafting personalised itineraries that cater to your travel style and preferences.
- Tailor-Made Itineraries: With Pickyourtrail, you get fully customised travel plans that match your preferences, budget, and schedule.
- Hassle-Free Planning: We take care of everything, from visa processing and flights to accommodations and local transfers.
- Exclusive Deals & Best Prices: Enjoy the best rates on flights, hotels, and experiences, ensuring great value for your trip with us.
- 24/7 On-Trip Assistance: You will get to travel with peace of mind knowing our team is available around the clock to support you.
- Seamless Digital Experience: Use our smart travel app to access itineraries, bookings, and real-time updates.
- Authentic Local Experiences: Immerse yourself in unique activities, from cultural tours to adventure sports, making your trip unforgettable.
Book your dream Chicago vacation with Pickyourtrail today and embark on a journey like never before!
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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
Hotels8 activities
Shared transfer
24x7 concierge
AED 10,262
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
Love from our travellersView all
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
Love from our 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
Usa City Packages
Las Vegas Tour PackagesAED 75,262/Person
Miami Tour PackagesAED 92,439/Person
New York Tour PackagesAED 75,262/Person
San Francisco Tour PackagesAED 107,912/Person
Chicago Tour PackagesAED 75,262/Person
Orlando Tour PackagesAED 107,178/Person
Boston Tour PackagesAED 127,797/Person
Los Angeles Tour PackagesAED 75,262/Person
Atlanta Tour PackagesAED 124,768/Person
Orlando Tour PackagesAED 107,178/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
Anjali Hp Reviewed on :06 Apr 2025
We had a Bali trip organized by Pickyourtrail. We must say that from start to end, everything was seamless. Everything was well organized. We felt completely taken care of and it made our trip stress free and enjoyable.
Anjali Hp Reviewed on :06 Apr 2025
We had a Bali trip organized by Pickyourtrail. We must say that from start to end, everything was seamless. Everything was well organized. We felt completely taken care of and it made our trip stress free and enjoyable.
Nirmal Yaram Reviewed on :06 Apr 2025
Nithin Kalyan deserves the Best Employee Award at PickYourTrail. My family had the smoothest and the most organized and fun filled Thailand trip ever. Loved the way Nithin planned everything for us and hats off to his patience level as we were changing options to best fit our trip. The private transfers, the coordination with the drivers and hotels there was on point. The trip was tailored for us by Nithin in such a way that it was budget friendly for us and at the same time, it was super convenient and extremely satisfactory. We are 100% booking our next trip this year with PickYourTrail and we definitely need Nithin Kalyan for it... Great job guys.!!!!
Nirmal Yaram Reviewed on :06 Apr 2025
Nithin Kalyan deserves the Best Employee Award at PickYourTrail. My family had the smoothest and the most organized and fun filled Thailand trip ever. Loved the way Nithin planned everything for us and hats off to his patience level as we were changing options to best fit our trip. The private transfers, the coordination with the drivers and hotels there was on point. The trip was tailored for us by Nithin in such a way that it was budget friendly for us and at the same time, it was super convenient and extremely satisfactory. We are 100% booking our next trip this year with PickYourTrail and we definitely need Nithin Kalyan for it... Great job guys.!!!!
Lalith Kiran Reviewed on :03 Apr 2025
It was good. We had booked an amazing stay with them in Maldives. Travel advisor interaction could have been better but overall it was an amazing experience for us
Lalith Kiran Reviewed on :03 Apr 2025
It was good. We had booked an amazing stay with them in Maldives. Travel advisor interaction could have been better but overall it was an amazing experience for us
Dr. Kishor Reviewed on :03 Apr 2025
One of the best trip organiser that I have ever Seen. their systems and processes are extremely good. They have a thorough idea to customise the Trip by selecting the best hotels and activities. I went to Spain and Portugal and it was truly a well organised vacation. Mr Mithun and Miss Shamanthika were extremely helpful and kind to clear all my doubts and apprehensions.As an icing on the cake their online support system is a show stopper. Their timely support is incredible and very helpful during the trip. As an avid traveller having been travelled for more than 15 countries over these 25 years, I would close my eyes and opt for Pick Your trial for my next vacation.
Dr. Kishor Reviewed on :03 Apr 2025
One of the best trip organiser that I have ever Seen. their systems and processes are extremely good. They have a thorough idea to customise the Trip by selecting the best hotels and activities. I went to Spain and Portugal and it was truly a well organised vacation. Mr Mithun and Miss Shamanthika were extremely helpful and kind to clear all my doubts and apprehensions.As an icing on the cake their online support system is a show stopper. Their timely support is incredible and very helpful during the trip. As an avid traveller having been travelled for more than 15 countries over these 25 years, I would close my eyes and opt for Pick Your trial for my next vacation.
Preethi Karthik Krishnan Reviewed on :02 Apr 2025
I wish to thank each and everyone at PickYourTrail to have made our trips happy and memorable right from our planning till execution! Our salute to PYT and team ! Love you guys always
Preethi Karthik Krishnan Reviewed on :02 Apr 2025
I wish to thank each and everyone at PickYourTrail to have made our trips happy and memorable right from our planning till execution! Our salute to PYT and team ! Love you guys always
Rakshith Mahadev Reviewed on :01 Apr 2025
We had a well organised trip to Maldives by Pickyourtrail.
Rakshith Mahadev Reviewed on :01 Apr 2025
We had a well organised trip to Maldives by Pickyourtrail.
Sowmiya Kumar Reviewed on :01 Apr 2025
We had booked our trip to Bali with Pickyourtrail. It was well organized.. the 24/7 assistance helped a lot! Although there was a hitch in our hotel booking (fault of the hotel management), PYT team responded immediately and arranged for a suitable alternative on time! All the stay places arranged by them were upto mark and the itinerary was well planned with ample time for leisure. Good work by Pickyourtrail.
Sowmiya Kumar Reviewed on :01 Apr 2025
We had booked our trip to Bali with Pickyourtrail. It was well organized.. the 24/7 assistance helped a lot! Although there was a hitch in our hotel booking (fault of the hotel management), PYT team responded immediately and arranged for a suitable alternative on time! All the stay places arranged by them were upto mark and the itinerary was well planned with ample time for leisure. Good work by Pickyourtrail.
Divya Sankar Reviewed on :01 Apr 2025
We recently went on a trip to Bali planned and arranged by Pickyourtrail. It was very well planned starting from hotel selection, private transfers and itinerary. I would highly recommend their services if you are planning a trip
Divya Sankar Reviewed on :01 Apr 2025
We recently went on a trip to Bali planned and arranged by Pickyourtrail. It was very well planned starting from hotel selection, private transfers and itinerary. I would highly recommend their services if you are planning a trip
Vinay Puree Reviewed on :31 Mar 2025
We recently went on a trip to Jakarta and Bali. This was all arranged by PYT. ITINERARY was very well planned, hotel selection, transfers were extremely wonderful. I will strongly recommend their services for planning a vacation.
Vinay Puree Reviewed on :31 Mar 2025
We recently went on a trip to Jakarta and Bali. This was all arranged by PYT. ITINERARY was very well planned, hotel selection, transfers were extremely wonderful. I will strongly recommend their services for planning a vacation.
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