Begin a journey that best defines Chicago by availing of our excellent Chicago packages based on personalized needs and interests. Whether you're a seeker of adventure activities, a cultural enthusiast, or someone simply looking to chill out and unwind, Pickyourtrail really has you covered with all types of Chicago vacation packages that suit every type of traveler. Be it creating the most beautiful landscapes, rich historical places, local delicacies, or those unique to your experiences.

Chicago Package Inclusions

Accommodation
Meals
Flights
Airport Transfers
Sightseeing
Local Transportation
Visa
Support
Customizable Itinerary

Chicago Package Exclusions

Personal Expenses
Optional Activities

Why Choose Pickyourtrail?

Customisable Packages: Our packages are customizable so that you can create your own likes and travel style. An intimate escape can be from luxury or adventure to relaxation; we have the right package for you.
Expertise & Knowledge: Our team is acquainted with every nook and cranny of Chicago, so you get the best recommendations and local insights, and because they are off the beaten track, it won't be any fun if everybody knows about them.
Customer-Centric: With 24/7 support in place to help you make each moment of your vacation memorable, Pickyourtrail aims to offer you a travel experience above others.
The Award-Winning Brand: We are known as one of the best in the business, offering high-quality travel experiences along with seamless booking and utmost satisfaction.

Let Pickyourtrail help you create unforgettable memories in Chicago with expertly crafted vacation packages. You can book your dream vacation today and enjoy the sights and sounds of Chicago uniquely!

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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

Bhoomika Mehta

Reviewed on :08 Jul 2025

I recently had the pleasure of booking a trip through Pick Your Trail, and I couldnt be more impressed with the entire experience. From the moment we started planning until the final day of our journey, everything was perfectly organized and stress-free. The itinerary was well thought out, offering the perfect balance between sightseeing, relaxation, and local experiences, just a bit problem for Pure Vegetarians. Our guide was knowledgeable, friendly, and went above and beyond to make sure everyone was comfortable and engaged. Transportation was punctual and clean, and all accommodations exceeded our expectations.

Bhoomika Mehta

Reviewed on :08 Jul 2025

Santhosh Kumaar

Reviewed on :08 Jul 2025

It was a good experience and everyone should opt for Pick your trail especially if you are planning for abroad

Santhosh Kumaar

Reviewed on :08 Jul 2025

It was a good experience and everyone should opt for Pick your trail especially if you are planning for abroad

Praveen Kotre

Reviewed on :07 Jul 2025

Had a great experience. Pick your trail truly offers a hassle free holiday.

Praveen Kotre

Reviewed on :07 Jul 2025

Had a great experience. Pick your trail truly offers a hassle free holiday.

Giri Dharan

Reviewed on :06 Jul 2025

Pattaya stay was good but in Bangkok stay was little uncomfortable. Overall trip was good and peaceful. Thanks

Giri Dharan

Reviewed on :06 Jul 2025

Pattaya stay was good but in Bangkok stay was little uncomfortable. Overall trip was good and peaceful. Thanks

Amarjeet Kaur

Reviewed on :03 Jul 2025

Best itnary and best hotels offered by compaby reperesentative specially Pradweep and Prem Nath. A nice trip wd value money offered. Better than maje my trip.

Amarjeet Kaur

Reviewed on :03 Jul 2025

Best itnary and best hotels offered by compaby reperesentative specially Pradweep and Prem Nath. A nice trip wd value money offered. Better than maje my trip.

Megha Gupta

Reviewed on :03 Jul 2025

We like the services and the app. They were very helpful.

Megha Gupta

Reviewed on :03 Jul 2025

We like the services and the app. They were very helpful.

Vamsi Pradeep

Reviewed on :02 Jul 2025

Hey, we just got back from our first Schengen trip to Italy and swiss with PYT, and it was awesome! The whole thing went super smoothly, and a big shoutout to the Visa team they were lifesavers, especially since our visa got rejected at first. Uma helped us plan everything, and Mohasib kept things running perfectly. Plus, the app support was great, with reminders and quick answers to all our questions. Seriously, I totally recommend PYT if you want a stress-free trip!

Vamsi Pradeep

Reviewed on :02 Jul 2025

Kailash Nirmal

Reviewed on :02 Jul 2025

I had a wonderful experience interacting with Hariharan ji from Pickyourtrail. I truly appreciate the time and effort he put into helping me. He patiently listened to all my queries, explained every detail clearly, and was always supportive and respectful throughout our conversations. His professionalism and dedication are commendable. He offered me multiple land packages for Thailand tailored to my preferences, and even after a few requests, he kindly extended a discount on the packages. That level of flexibility and customer care is rare. I highly recommend Hariharan ji to anyone looking for travel assistancehes truly a gem in customer support!

Kailash Nirmal