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Chicago Trip Packages
IDEAL DURATION4 nights
OUR EXPERTISE
4.2from 552 travellers
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Chicago Holiday Packages from UAE

The fun doesn't just stop Here. The wanderlust in you is bound to augment once you check out our various theme based packages for other destinations like New Zealand, Europe, and Australia. Planning to take a family vacation or set out on an adventurous holiday with your friends? We have customisable packages catering to them as well. All you need to do is let us know your interests and preferences; and your holiday package is ready to go.
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Reviews from Usa travellers
Arpana Devarhubli-Profile
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-Profile
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
Sanjay Pandey-Profile
Sanjay Pandey
Reviewed on :17 Jul 2025
Smooth trip, sweet memories all thanks to @pickyourtrail! We booked our Bali trip through Pickyourtrail, and honestly, it turned out to be one of the smoothest and most memorable travel experiences weve ever had. From planning to touchdown back home, their support team truly redefined the meaning of support. Not a single hiccup throughout the journey! Special shoutout to our travel guide Penu so humble, kind, and helpful. He made our trip even more special. We went to celebrate our anniversary and came back with a heart full of memories. Thank you, Pickyourtrail, for making it a trip well always treasure. Looking forward to our next adventure with you!
Sanjay Pandey-testimonial-0
Sanjay Pandey-testimonial-1
Sanjay Pandey-Profile
Sanjay Pandey
Reviewed on :17 Jul 2025
Smooth trip, sweet memories all thanks to @pickyourtrail! We booked our Bali trip through Pickyourtrail, and honestly, it turned out to be one of the smoothest and most memorable travel experiences weve ever had. From planning to touchdown back home, their support team truly redefined the meaning of support. Not a single hiccup throughout the journey! Special shoutout to our travel guide Penu so humble, kind, and helpful. He made our trip even more special. We went to celebrate our anniversary and came back with a heart full of memories. Thank you, Pickyourtrail, for making it a trip well always treasure. Looking forward to our next adventure with you!
Sanjay Pandey-testimonial-0
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Rasika Joshi-Profile
Rasika Joshi
Reviewed on :17 Jul 2025
I got my trip booked for Bali from Pickyourtrail. All the arrangements were excellent. They had 24x7 live chat during the trip which was helpful. Would certainly recommend Pickyourtrail
Rasika Joshi-Profile
Rasika Joshi
Reviewed on :17 Jul 2025
I got my trip booked for Bali from Pickyourtrail. All the arrangements were excellent. They had 24x7 live chat during the trip which was helpful. Would certainly recommend Pickyourtrail
KALYANASUNDARAM BAKTHAVATCHALAM-Profile
Kalyanasundaram Bakthavatchalam
Reviewed on :17 Jul 2025
International tours are reliable and best for family trips. We can corporate official person for any help from our tour locations, they will arrange solutions at our tour place
KALYANASUNDARAM BAKTHAVATCHALAM-Profile
Kalyanasundaram Bakthavatchalam
Reviewed on :17 Jul 2025
International tours are reliable and best for family trips. We can corporate official person for any help from our tour locations, they will arrange solutions at our tour place
shyam Jagetiya-Profile
Shyam Jagetiya
Reviewed on :17 Jul 2025
Good experience at great price! Had everything coordinated clearly and smooth experience
shyam Jagetiya-Profile
Shyam Jagetiya
Reviewed on :17 Jul 2025
Good experience at great price! Had everything coordinated clearly and smooth experience
Ojas Oza-Profile
Ojas Oza
Reviewed on :17 Jul 2025
A fantastic tour plan by Pickyourtrail team. I highly recommend.
Ojas Oza-Profile
Ojas Oza
Reviewed on :17 Jul 2025
A fantastic tour plan by Pickyourtrail team. I highly recommend.
Srinath M.S-Profile
Srinath M.s
Reviewed on :17 Jul 2025
They arranged everything perfectly.. Guided us throught the trip... solved the queries entirely during the trip via chat support. 24/7
Srinath M.S-Profile
Srinath M.s
Reviewed on :17 Jul 2025
They arranged everything perfectly.. Guided us throught the trip... solved the queries entirely during the trip via chat support. 24/7
Vishwathmika Gananathar-Profile
Vishwathmika Gananathar
Reviewed on :17 Jul 2025
Whole experience in bali was like being in mothers arm ,felt safe and had fun . Pick your trail agents instant help through chat and resolution was fantastic! Everything was on time! And felt very comfortable! We will definitely choose PYT for our next trip!
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Vishwathmika Gananathar-testimonial-1
Vishwathmika Gananathar-testimonial-2
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Vishwathmika Gananathar-Profile
Vishwathmika Gananathar
Reviewed on :17 Jul 2025
Whole experience in bali was like being in mothers arm ,felt safe and had fun . Pick your trail agents instant help through chat and resolution was fantastic! Everything was on time! And felt very comfortable! We will definitely choose PYT for our next trip!
Vishwathmika Gananathar-testimonial-0
Vishwathmika Gananathar-testimonial-1
Vishwathmika Gananathar-testimonial-2
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Sivasubramanian M-Profile
Sivasubramanian M
Reviewed on :17 Jul 2025
No nonsense, hassle free trip booking experience. From the initial chat to the end the of trip PickYourTrail team was providing an excellent service. Their team knew what are the do's and don'ts and recommended what is the best way to enjoy the trip. They even went an extra mile and checked in on us during our trip to ensure that we are having a good time. If you want to plan a trip, I highly recommend PYT first, check them out and see what they have to offer and then decide. Unlike the conventional trip planners, their team is young and proactive, provide you good recommendations and suggestions.
Sivasubramanian M-Profile
Sivasubramanian M
Reviewed on :17 Jul 2025
No nonsense, hassle free trip booking experience. From the initial chat to the end the of trip PickYourTrail team was providing an excellent service. Their team knew what are the do's and don'ts and recommended what is the best way to enjoy the trip. They even went an extra mile and checked in on us during our trip to ensure that we are having a good time. If you want to plan a trip, I highly recommend PYT first, check them out and see what they have to offer and then decide. Unlike the conventional trip planners, their team is young and proactive, provide you good recommendations and suggestions.
Nandan R-Profile
Nandan R
Reviewed on :13 Jul 2025
The best and professional Agency! I recently selected PYT as my travel partner to BALI and they perfected it. A special thanks to @Dikshita (Sales), @Rishika (Dikshi Lead), & Diwakar (Trip custodian) for planning, booking and making it a hassle free vacation . Vacation, itinerary & support was quick and seemless! The travel in Bali was made cool & calm by Mr. Professional Joe to Mr. Friendly & famous Mr. Arna at Bali & Nusa Penida. Expect for few setbacks rest were good. Thanks much to PYT team for making this a memorable and amazing vacation.
Nandan R-Profile
Nandan R
Reviewed on :13 Jul 2025
The best and professional Agency! I recently selected PYT as my travel partner to BALI and they perfected it. A special thanks to @Dikshita (Sales), @Rishika (Dikshi Lead), & Diwakar (Trip custodian) for planning, booking and making it a hassle free vacation . Vacation, itinerary & support was quick and seemless! The travel in Bali was made cool & calm by Mr. Professional Joe to Mr. Friendly & famous Mr. Arna at Bali & Nusa Penida. Expect for few setbacks rest were good. Thanks much to PYT team for making this a memorable and amazing vacation.
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