IDEAL DURATION4 nights
STARTING PRICE$231,583
OUR EXPERTISE
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!
...Read more
Budget
Hotel ratings
Thailand is now visa-free for Indian travellers - book your holiday now 
Incredible 14 day USA itinerary for the Solo travellers
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$2,810
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
Love from our travellersView all
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
Love from our 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
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
Usa City Packages
New York Tour Packages$75,262/Person
Las Vegas Tour Packages$75,262/Person
Los Angeles Tour Packages$75,262/Person
Boston Tour Packages$129,777/Person
Orlando Tour Packages$107,178/Person
Miami Tour Packages$92,439/Person
San Francisco Tour Packages$127,929/Person
Chicago Tour Packages$75,262/Person
Atlanta Tour Packages$183,531/Person
Orlando Tour Packages$107,178/Person
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
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
Anjali Hp Reviewed on :06 Apr 2025
We had a Bali trip organized by Pickyourtrail. We must say that from start to end, everything was seamless. Everything was well organized. We felt completely taken care of and it made our trip stress free and enjoyable.
Anjali Hp Reviewed on :06 Apr 2025
We had a Bali trip organized by Pickyourtrail. We must say that from start to end, everything was seamless. Everything was well organized. We felt completely taken care of and it made our trip stress free and enjoyable.
Nirmal Yaram Reviewed on :06 Apr 2025
Nithin Kalyan deserves the Best Employee Award at PickYourTrail. My family had the smoothest and the most organized and fun filled Thailand trip ever. Loved the way Nithin planned everything for us and hats off to his patience level as we were changing options to best fit our trip. The private transfers, the coordination with the drivers and hotels there was on point. The trip was tailored for us by Nithin in such a way that it was budget friendly for us and at the same time, it was super convenient and extremely satisfactory. We are 100% booking our next trip this year with PickYourTrail and we definitely need Nithin Kalyan for it... Great job guys.!!!!
Nirmal Yaram Reviewed on :06 Apr 2025
Nithin Kalyan deserves the Best Employee Award at PickYourTrail. My family had the smoothest and the most organized and fun filled Thailand trip ever. Loved the way Nithin planned everything for us and hats off to his patience level as we were changing options to best fit our trip. The private transfers, the coordination with the drivers and hotels there was on point. The trip was tailored for us by Nithin in such a way that it was budget friendly for us and at the same time, it was super convenient and extremely satisfactory. We are 100% booking our next trip this year with PickYourTrail and we definitely need Nithin Kalyan for it... Great job guys.!!!!
Lalith Kiran Reviewed on :03 Apr 2025
It was good. We had booked an amazing stay with them in Maldives. Travel advisor interaction could have been better but overall it was an amazing experience for us
Lalith Kiran Reviewed on :03 Apr 2025
It was good. We had booked an amazing stay with them in Maldives. Travel advisor interaction could have been better but overall it was an amazing experience for us
Dr. Kishor Reviewed on :03 Apr 2025
One of the best trip organiser that I have ever Seen. their systems and processes are extremely good. They have a thorough idea to customise the Trip by selecting the best hotels and activities. I went to Spain and Portugal and it was truly a well organised vacation. Mr Mithun and Miss Shamanthika were extremely helpful and kind to clear all my doubts and apprehensions.As an icing on the cake their online support system is a show stopper. Their timely support is incredible and very helpful during the trip. As an avid traveller having been travelled for more than 15 countries over these 25 years, I would close my eyes and opt for Pick Your trial for my next vacation.
Dr. Kishor Reviewed on :03 Apr 2025
One of the best trip organiser that I have ever Seen. their systems and processes are extremely good. They have a thorough idea to customise the Trip by selecting the best hotels and activities. I went to Spain and Portugal and it was truly a well organised vacation. Mr Mithun and Miss Shamanthika were extremely helpful and kind to clear all my doubts and apprehensions.As an icing on the cake their online support system is a show stopper. Their timely support is incredible and very helpful during the trip. As an avid traveller having been travelled for more than 15 countries over these 25 years, I would close my eyes and opt for Pick Your trial for my next vacation.
Preethi Karthik Krishnan Reviewed on :02 Apr 2025
I wish to thank each and everyone at PickYourTrail to have made our trips happy and memorable right from our planning till execution! Our salute to PYT and team ! Love you guys always
Preethi Karthik Krishnan Reviewed on :02 Apr 2025
I wish to thank each and everyone at PickYourTrail to have made our trips happy and memorable right from our planning till execution! Our salute to PYT and team ! Love you guys always
Rakshith Mahadev Reviewed on :01 Apr 2025
We had a well organised trip to Maldives by Pickyourtrail.
Rakshith Mahadev Reviewed on :01 Apr 2025
We had a well organised trip to Maldives by Pickyourtrail.
Sowmiya Kumar Reviewed on :01 Apr 2025
We had booked our trip to Bali with Pickyourtrail. It was well organized.. the 24/7 assistance helped a lot! Although there was a hitch in our hotel booking (fault of the hotel management), PYT team responded immediately and arranged for a suitable alternative on time! All the stay places arranged by them were upto mark and the itinerary was well planned with ample time for leisure. Good work by Pickyourtrail.
Sowmiya Kumar Reviewed on :01 Apr 2025
We had booked our trip to Bali with Pickyourtrail. It was well organized.. the 24/7 assistance helped a lot! Although there was a hitch in our hotel booking (fault of the hotel management), PYT team responded immediately and arranged for a suitable alternative on time! All the stay places arranged by them were upto mark and the itinerary was well planned with ample time for leisure. Good work by Pickyourtrail.
Divya Sankar Reviewed on :01 Apr 2025
We recently went on a trip to Bali planned and arranged by Pickyourtrail. It was very well planned starting from hotel selection, private transfers and itinerary. I would highly recommend their services if you are planning a trip
Divya Sankar Reviewed on :01 Apr 2025
We recently went on a trip to Bali planned and arranged by Pickyourtrail. It was very well planned starting from hotel selection, private transfers and itinerary. I would highly recommend their services if you are planning a trip
Vinay Puree Reviewed on :31 Mar 2025
We recently went on a trip to Jakarta and Bali. This was all arranged by PYT. ITINERARY was very well planned, hotel selection, transfers were extremely wonderful. I will strongly recommend their services for planning a vacation.
Vinay Puree Reviewed on :31 Mar 2025
We recently went on a trip to Jakarta and Bali. This was all arranged by PYT. ITINERARY was very well planned, hotel selection, transfers were extremely wonderful. I will strongly recommend their services for planning a vacation.
Partnered with the best in the industry
International Holiday Destinations From Usa
Europe Specials
Austria Packages from USBelarus Packages from USBelgium Packages from USCroatia Packages from USCzech Republic Packages from USDenmark Packages from USEstonia Packages from USFinland Packages from USFrance Packages from USGermany Packages from USGreece Packages from USHungary Packages from USIceland Packages from USIreland Packages from USItaly Packages from USLatvia Packages from USMalta Packages from USMonaco Packages from USNetherlands Packages from USNorway Packages from USPoland Packages from USPortugal Packages from USRomania Packages from USSpain Packages from USSweden Packages from USSwitzerland Packages from USUnited Kingdom Packages from US
Popular Honeymoon Tour Packages
Combo Packages
Bali Thailand Packages from USCambodia Bali Packages from USFrance Switzerland Packages from USGreece Turkey Packages from USMalaysia Bali Packages from USParis Barcelona Packages from USParis Switzerland Italy Packages from USPrague Vienna Budapest Packages from USSingapore Bali Thailand Packages from USThailand Cambodia Packages from USThailand Cambodia Vietnam Packages from USThailand Vietnam Packages from USBali Singapore Packages from US
We think you are in .
Update your location?
Update your location?