View All Media

Home
Itineraries
The ultimate 7 night itinerary to fall in love with Chicago and New York

Why choose Pickyourtrail?

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 India

Itinerary

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/ person

Excluding Applicable Taxes

Your route

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

4.7

From 8250 reviews

Verified Reviews

Photos from Travellers

Pickyourtrail's Original Reviews

Arpana Devarhubli

Reviewed on :07 Oct 2024

Arpana Devarhubli

Reviewed on :07 Oct 2024

Kaustubh Bobade

Reviewed on :23 Feb 2026

Great Experience and thanks to them, we had great vacation

Kaustubh Bobade

Reviewed on :23 Feb 2026

Great Experience and thanks to them, we had great vacation

Amla Khadilkar

Reviewed on :23 Feb 2026

Good experience..

Amla Khadilkar

Reviewed on :23 Feb 2026

Good experience..

Amit Kulkarni

Reviewed on :23 Feb 2026

We went for our honeymoon from pickyourtrail and it was awesome great choices of resort in our budget and the trip was smooth everything thing was communicated in advance to us and all queries were answered asap especially during the trip they have 24x7 doubt service Highly recommended!!