Login
Holiday Tour Packages
Family Theme Packages
Honeymoon Theme Packages
Adventure Theme Packages
Exclusive Packages
Choose country
PYT - IndiaPYT - United StatesPYT - United Arab Emirates
Fetching itinerary costings...
View All Media
- Home
- Packages
- Usa Packages
- The ultimate 7 night itinerary to fall in love with Chicago and New York
Why choose Pickyourtrail?
Awarded The Best Holiday Brand in India
1 Million+ Itineraries CuratedAcross 100+ destinations in the past 12 years
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
4 Nights Stay
Chicago — 4 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
Day 04
Morning
Zombie Scavengers Game - Springfield, IL
Noon to Evening
At leisure. Add Activity
Fly to New York
New York
3 Nights Stay
New York — 3 Nights
Day 05
Morning
At leisure. Add Activity
Noon to Evening
Checkout of your hotel. Board your flight to New York. Check-in to your new hotel in New York
Day 06
Morning
Medieval Times Dinner and Tournament in Lyndhurst, New Jersey
Noon to Evening
At leisure. Add Activity
Day 07
Morning
Historic Richmond Town Admission
Noon to Evening
At leisure. Add Activity
Day 08
Full Day
Take your flight back home. Hope you end up with a lot of memories and a few souvenirs too.
Add trip details
₹136,819
7 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
Ravindra Govindani Reviewed on :13 Jan 2026
Had really good experience on my philippines trip
Ravindra Govindani Reviewed on :13 Jan 2026
Had really good experience on my philippines trip
Rajarajan Velumani Reviewed on :13 Jan 2026
PYT has been a great partner for us both during our 2021 anniversary trip to Maldives and again now to celebrate our daughters first birthday. Everything has been extraordinary across both the instances. For our 2026 trip just wanted to call out the efforts of Sneha who helped us with the planning and Hari Haran for his post booking support. I didnt want any hazzle during a trip with my 1-year old and they both ensured the same from the date of confirmation till the last day of the trip. Thank you both :)
Rajarajan Velumani Reviewed on :13 Jan 2026
PYT has been a great partner for us both during our 2021 anniversary trip to Maldives and again now to celebrate our daughters first birthday. Everything has been extraordinary across both the instances. For our 2026 trip just wanted to call out the efforts of Sneha who helped us with the planning and Hari Haran for his post booking support. I didnt want any hazzle during a trip with my 1-year old and they both ensured the same from the date of confirmation till the last day of the trip. Thank you both :)
Sandeep Koluvail Reviewed on :13 Jan 2026
A good travel group who helped with the Maldives trip.. The team was always there to address your questions and was regularly checking upon us during the trip..
+1View all
Sandeep Koluvail Reviewed on :13 Jan 2026
A good travel group who helped with the Maldives trip.. The team was always there to address your questions and was regularly checking upon us during the trip..
+1View all
Abhijit Jagtap Reviewed on :12 Jan 2026
Good experience
Abhijit Jagtap Reviewed on :12 Jan 2026
Good experience
Sayali Sawant Reviewed on :12 Jan 2026
Booked a 4 day Maldives trip with PYT. They offered us good deals and made sure our travel was hassle free. All pick up-drop offs were well planned. Pre travel information was shared timely and the employees checked on us every day.
+1View all
Sayali Sawant Reviewed on :12 Jan 2026
Booked a 4 day Maldives trip with PYT. They offered us good deals and made sure our travel was hassle free. All pick up-drop offs were well planned. Pre travel information was shared timely and the employees checked on us every day.
+1View all
4.7From 8250 reviews
Verified ReviewsSimilar Itineraries
Partnered with the best in the industry
International Holiday Destinations
Australia Holiday PackagesDubai Holiday PackagesSingapore Holiday PackagesThailand Holiday PackagesBali Holiday PackagesMaldives Holiday PackagesSeychelles Holiday PackagesVietnam Holiday PackagesNew Zealand Holiday PackagesJapan Holiday PackagesMalaysia Holiday PackagesIceland Holiday PackagesSri Lanka Holiday PackagesFrance Holiday PackagesSwitzerland Holiday PackagesUnited States Holiday PackagesSaudi Arabia Holiday PackagesItaly Holiday PackagesGermany Holiday PackagesMauritius Holiday PackagesUK Holiday PackagesGreece Holiday Packages
We think you are in .
Update your location?
Update your location?