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Why choose Pickyourtrail?
Awarded The Best Holiday Brand in India
12+ Years of ExpertiseCurated experiences to make every holiday a sooper hit.
1,50,000+ HolidaysFrom honeymoons to family getaways, customised with care and delight.
Rated 4.6⭐ on Google8000+ reviews from travellers who had a sooper hit holiday.
24x7 Customer SupportOn-trip help when you need it. No bots, just real people.
Awarded The Best Holiday Brand in IndiaItinerary
Chicago
3 Nights Stay
Chicago — 3 Nights
Day 01
Morning to Noon
Arrive in Chicago airport. Get transferred to your hotel.
Evening
At leisure. Add Activity
Day 02
Morning
Macy's Center City History Tour in Philadelphia
Noon
WINTER ARCHITECTURE TOUR
Evening
3-Hour Walking Tour: Chicago World's Fair of 1893
Day 03
Full Day
Driehaus Museum Admission
Fly to Boston
Boston
2 Nights Stay
Boston — 2 Nights
Day 04
Morning
At leisure. Add Activity
Noon
Checkout of your hotel. Board your flight to Boston. Check-in to your new hotel in Boston
Evening
At leisure. Add Activity
Day 05
Morning
Zombie Scavengers Game - Lowell, MA
Noon to Evening
At leisure. Add Activity
Fly to Orlando
Orlando
2 Nights Stay
Orlando — 2 Nights
Day 06
Morning
Checkout of your hotel. Board your flight to Orlando. Check-in to your new hotel in Orlando
Noon to Evening
At leisure. Add Activity
Day 07
Morning
Medieval Times Dinner and Tournament in Orlando
Noon to Evening
At leisure. Add Activity
Fly to Buffalo
Buffalo
2 Nights Stay
Buffalo — 2 Nights
Day 08
Morning
At leisure. Add Activity
Noon
Checkout of your hotel. Board your flight to Buffalo. Check-in to your new hotel in Buffalo
Evening
At leisure. Add Activity
Day 09
Full Day
At leisure. Add Activity
Day 10
Full Day
Take your flight back home. Hope you end up with a lot of memories and a few souvenirs too.
Add trip details
₹218,424
9 nights / person
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 oneArpana Devarhubli, Trip to USA
See what’s included in this tripCost your itinerary to see the hotels, flights, and activities included in your trip
4.7From 8250 reviews
Verified ReviewsPhotos from Travellers
Pickyourtrail's Original Reviews
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
Shubham Dey Reviewed on :21 Dec 2025
Pickyourtrail, had curated the trip very nicely and they were very accommodating with my requests. The team helped me with all the requirements and the on site help was amazing with all the details provided a day before. Rituraj and Divya from the PYT team had helped me with all the queries. Looking forward to book another trip with PYT.
Shubham Dey Reviewed on :21 Dec 2025
Pickyourtrail, had curated the trip very nicely and they were very accommodating with my requests. The team helped me with all the requirements and the on site help was amazing with all the details provided a day before. Rituraj and Divya from the PYT team had helped me with all the queries. Looking forward to book another trip with PYT.
Bharathwaaj Murugan Reviewed on :21 Dec 2025
we booked a trip to thailand, everything went smooth. overall good experience.
Bharathwaaj Murugan Reviewed on :21 Dec 2025
we booked a trip to thailand, everything went smooth. overall good experience.
Chakravathi Subbarao Reviewed on :21 Dec 2025
We had a great experience
Chakravathi Subbarao Reviewed on :21 Dec 2025
We had a great experience
Pawan Kerkar Reviewed on :21 Dec 2025
I planned my honeymoon in the Maldives with Pickyourtrail. I would highly recommend them for a smooth and hassle-free trip planning and execution experience.
Pawan Kerkar Reviewed on :21 Dec 2025
I planned my honeymoon in the Maldives with Pickyourtrail. I would highly recommend them for a smooth and hassle-free trip planning and execution experience.
Dhinesh Kumar Reviewed on :21 Dec 2025
PickYourTrail has very good people in supporting customers 24/7 and providing technical support through application also.Providing end to end support throughout your journey and make you hassle free.
Dhinesh Kumar Reviewed on :21 Dec 2025
PickYourTrail has very good people in supporting customers 24/7 and providing technical support through application also.Providing end to end support throughout your journey and make you hassle free.
4.7From 8250 reviews
Verified ReviewsSimilar Itineraries
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