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Chicago Trip Packages
IDEAL DURATION4 nights
OUR EXPERTISE
4.2from 552 travellers
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Chicago Vacation Packages from USA

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-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
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.
Poorvaja Ks-Profile
Poorvaja Ks
Reviewed on :13 Jul 2025
Hi, firstly thank you PYT for this wonderful trip. We recently went on 5-day trip to Bali, and it was an absolutely wonderful experience! Right from the booking process to daily itinerary, everything was smooth, well-organized, and stress-free. The app made it super easy to track our schedule and vouchers. Bali local driver guide were punctual, polite, always ensuring we were comfortable. His name is Wayan. The hotel selection was also spot-on. Once again thank you to Pickyourtrail team for being available whenever we had doubts.
Poorvaja Ks-Profile
Poorvaja Ks
Reviewed on :13 Jul 2025
Hi, firstly thank you PYT for this wonderful trip. We recently went on 5-day trip to Bali, and it was an absolutely wonderful experience! Right from the booking process to daily itinerary, everything was smooth, well-organized, and stress-free. The app made it super easy to track our schedule and vouchers. Bali local driver guide were punctual, polite, always ensuring we were comfortable. His name is Wayan. The hotel selection was also spot-on. Once again thank you to Pickyourtrail team for being available whenever we had doubts.
Raj Sinha-Profile
Raj Sinha
Reviewed on :13 Jul 2025
My experience in this trip was great and memorable, the tour manager Ms. Martha and the coach driver were very sweet and helpful. We made great memories and very good friends. We shall soon travel with you again in the future Thanks for your support
Raj Sinha-testimonial-0
Raj Sinha-Profile
Raj Sinha
Reviewed on :13 Jul 2025
My experience in this trip was great and memorable, the tour manager Ms. Martha and the coach driver were very sweet and helpful. We made great memories and very good friends. We shall soon travel with you again in the future Thanks for your support
Raj Sinha-testimonial-0
Vinita Wani-Profile
Vinita Wani
Reviewed on :13 Jul 2025
Good and smooth experience from enquiry to finalising the booking to the departure and arrival from the trip.
Vinita Wani-Profile
Vinita Wani
Reviewed on :13 Jul 2025
Good and smooth experience from enquiry to finalising the booking to the departure and arrival from the trip.
Deepa Sharma-Profile
Deepa Sharma
Reviewed on :13 Jul 2025
Pick your trail did a good job for making our Bali trip memorable. It was smooth switch between the activities. All the pre preparations for the day was taken care of very nicely ,we didnt had to struggle one for anything.
Deepa Sharma-testimonial-0
Deepa Sharma-testimonial-1
Deepa Sharma-Profile
Deepa Sharma
Reviewed on :13 Jul 2025
Pick your trail did a good job for making our Bali trip memorable. It was smooth switch between the activities. All the pre preparations for the day was taken care of very nicely ,we didnt had to struggle one for anything.
Deepa Sharma-testimonial-0
Deepa Sharma-testimonial-1
Bhoomika Mehta-Profile
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-Profile
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.
Santhosh Kumaar-Profile
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-Profile
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-Profile
Praveen Kotre
Reviewed on :07 Jul 2025
Had a great experience. Pick your trail truly offers a hassle free holiday.
Praveen Kotre-Profile
Praveen Kotre
Reviewed on :07 Jul 2025
Had a great experience. Pick your trail truly offers a hassle free holiday.
Giri Dharan-Profile
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-Profile
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
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