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IDEAL DURATION4 nights
STARTING PRICE$87,090
OUR EXPERTISE
Chicago Travel 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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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
$2,773
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
A 13 night trip to incredible USA
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$2,773
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
Beautiful 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
$2,764
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
A Honeymoon itinerary: A fantastic 13 night USA trip
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$1,767
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
10 nights 11 days Incredible United States of America attraction Solo Holiday Package
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels7 activities
Shared transfer
24x7 concierge
$2,451
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
The perfect 14 day USA itinerary for the adventure lovers
13 nights:
Chicago (3N)
Washington D.C (2N)
+4 Cities
4.5
Hotels6 activities
Shared transfer
24x7 concierge
$2,192
per person- Macy's Center City History Tour in Philadelphia
+ 5 more
A 10 night trip to lovely USA
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels7 activities
Shared transfer
24x7 concierge
$2,788
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
An incredible 11 day USA itinerary for an unforgettable Family vacation
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels7 activities
Shared transfer
24x7 concierge
$2,307
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
A Solo itinerary: A fantastic 13 night USA trip
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$2,210
per person- 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
Art lover's holiday: Lose yourself in amazing USA
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels6 activities
Shared transfer
24x7 concierge
$1,186
per person- Macy's Center City History Tour in Philadelphia
+ 5 more
Ideal United States of America Honeymoon trip
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,365
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights 11 days Relaxing United States of America attraction Honeymoon trip
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,365
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Incredible United States of America Couple Package
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,365
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Honeymoon special: ideal 10 night trip to USA
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,053
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Kindling the beautiful in you : A perfect USA itinerary
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,393
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
An epic 10 night USA itinerary for the incredible
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,393
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Amazing 11 day trip to USA for Honeymoon
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,393
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Rejuvenating 11 day USA itinerary for the Honeymoon travellers
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,393
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
The best itinerary to explore the amazing side of USA
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,393
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
A 10 night trip to ideal USA
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,393
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Relaxing United States of America Honeymoon trip
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,123
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Beautiful United States of America Tour Package for Couple
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,123
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Incredible 11 day USA itinerary for the Honeymoon travellers
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,123
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Amazing United States of America Package for Couple
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,123
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
A 10 night trip to awesome USA
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,123
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
Incredible 10 night USA itinerary
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels5 activities
Shared transfer
24x7 concierge
$1,043
per person- Macy's Center City History Tour in Philadelphia
+ 4 more
Beautiful 11 day USA itinerary for the Honeymoon travellers
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,123
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
A Family itinerary: A fantastic 10 night USA trip
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels5 activities
Shared transfer
24x7 concierge
$1,167
per person- Macy's Center City History Tour in Philadelphia
+ 4 more
An epic 10 night USA itinerary for the ideal
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels5 activities
Shared transfer
24x7 concierge
$1,441
per person- Macy's Center City History Tour in Philadelphia
+ 4 more
The fabulous 10 night USA Family itinerary
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels10 activities
Shared transfer
24x7 concierge
$1,971
per person- Macy's Center City History Tour in Philadelphia
+ 9 more
Usa City Packages
Las Vegas Tour Packages$75,262/Person
Miami Tour Packages$92,439/Person
New York Tour Packages$75,262/Person
San Francisco Tour Packages$127,929/Person
Chicago Tour Packages$75,262/Person
Orlando Tour Packages$107,178/Person
Boston Tour Packages$129,777/Person
Los Angeles 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
Ramy Srineevasan Reviewed on :16 Mar 2025
Splendid experience... Great support from the team, before and after the trip's getting started... We loved it... One of the best honeymoon package we had in Maldives... Very grateful for it... Thank you so much team
Ramy Srineevasan Reviewed on :16 Mar 2025
Splendid experience... Great support from the team, before and after the trip's getting started... We loved it... One of the best honeymoon package we had in Maldives... Very grateful for it... Thank you so much team
Meetu Sharma Reviewed on :16 Mar 2025
Amazing travel experience! I recently booked a trip to Bali, Indonesia via Pickyourtrail, and I couldn't have been more satisfied with the service and mannerisms of the entire Pickyourtrail team, from Mr Sanjai C to Mr Darsana. After searching for travel agencies, I came across Pickyourtrail, and Sanjai C called me up, it took 3 days to finalise the itinerary after omitting and editing it numerous times. The chat support was very responsive, and Mr Sanjai went out of his way to help me even during late hours. He finalised the itinerary according to the budget. Thank you, Mr Sanjai! He worked on my itinerary till late night and kept even the minutest detail in mind while curating my plan. He became enthusiastic when I told him that this will be our first trip overseas and this is dedicated to our daughter as we will be travelling immediately after her exams to give her a nice break. Ms Tika, of Bali Bagus i.e the car agency too helped wherever required, everything was on time, was never left hanging. During our entire trip, we had 3 drivers, Mr Darsana(throughout the entire trip), Mr Jack and Mr Wendy(for one day). Mr Darsana, our driver, guide and photographer, could not have been more efficient. Always punctual and regular, whilst telling us all about the places we visited. Very polite and helpful, always smiling :) couldn't have asked for a better guide than him. In Nusa Penida, the second guide, Mr Jack, even in his short time with us helped us a lot, and was an amazing photographer. He met us on time, and the Nusa Penida trip went smoothly without any hassles. Am amazed at the coordination between the Bali Bagus team as they clicked our pictures to let each other know our details and when and where to meet! Mr Wendy, the third driver was with us for a very short period of time, from the Nusa Penida pick up point to the hotel, but in that time we learnt a lot about Bali and he himself in return learnt a lot about India. He had a good sense of humour and wide range knowledge as well. He has been a great fan of bollywood and Shahrukh Khan. I highly recommend Pickyourtrail to anyone looking for a stress-free and unforgettable travel experience. Ill definitely be using their services again and will recommend to my family and friends. Our hearts are filled with wonderful memories
+1View all
Meetu Sharma Reviewed on :16 Mar 2025
Amazing travel experience! I recently booked a trip to Bali, Indonesia via Pickyourtrail, and I couldn't have been more satisfied with the service and mannerisms of the entire Pickyourtrail team, from Mr Sanjai C to Mr Darsana. After searching for travel agencies, I came across Pickyourtrail, and Sanjai C called me up, it took 3 days to finalise the itinerary after omitting and editing it numerous times. The chat support was very responsive, and Mr Sanjai went out of his way to help me even during late hours. He finalised the itinerary according to the budget. Thank you, Mr Sanjai! He worked on my itinerary till late night and kept even the minutest detail in mind while curating my plan. He became enthusiastic when I told him that this will be our first trip overseas and this is dedicated to our daughter as we will be travelling immediately after her exams to give her a nice break. Ms Tika, of Bali Bagus i.e the car agency too helped wherever required, everything was on time, was never left hanging. During our entire trip, we had 3 drivers, Mr Darsana(throughout the entire trip), Mr Jack and Mr Wendy(for one day). Mr Darsana, our driver, guide and photographer, could not have been more efficient. Always punctual and regular, whilst telling us all about the places we visited. Very polite and helpful, always smiling :) couldn't have asked for a better guide than him. In Nusa Penida, the second guide, Mr Jack, even in his short time with us helped us a lot, and was an amazing photographer. He met us on time, and the Nusa Penida trip went smoothly without any hassles. Am amazed at the coordination between the Bali Bagus team as they clicked our pictures to let each other know our details and when and where to meet! Mr Wendy, the third driver was with us for a very short period of time, from the Nusa Penida pick up point to the hotel, but in that time we learnt a lot about Bali and he himself in return learnt a lot about India. He had a good sense of humour and wide range knowledge as well. He has been a great fan of bollywood and Shahrukh Khan. I highly recommend Pickyourtrail to anyone looking for a stress-free and unforgettable travel experience. Ill definitely be using their services again and will recommend to my family and friends. Our hearts are filled with wonderful memories
+1View all
Rahul Kumar Reviewed on :16 Mar 2025
It was good experience booking Maldives Package from PickYourTrail.
Rahul Kumar Reviewed on :16 Mar 2025
It was good experience booking Maldives Package from PickYourTrail.
Amiya Rath Reviewed on :15 Mar 2025
Excellent follow up by Sharon makes our travel more comfortable Similarly Dinesh Aldo helped a lot for logistic and other arrangement Overall experience is Wow!!!!
Amiya Rath Reviewed on :15 Mar 2025
Excellent follow up by Sharon makes our travel more comfortable Similarly Dinesh Aldo helped a lot for logistic and other arrangement Overall experience is Wow!!!!
Kumudha Rajendran Reviewed on :15 Mar 2025
Well organised trip tailored to our needs. We went to Cambodia and Vietnam and got to see places we wanted to. Tie up with local travel agents and tour guides and drivers worked seamlessly. WhatsApp groups were very helpful. Would highly recommend. Thanks to Nirinder and Divya and all others who suggested and coordinated.
Kumudha Rajendran Reviewed on :15 Mar 2025
Well organised trip tailored to our needs. We went to Cambodia and Vietnam and got to see places we wanted to. Tie up with local travel agents and tour guides and drivers worked seamlessly. WhatsApp groups were very helpful. Would highly recommend. Thanks to Nirinder and Divya and all others who suggested and coordinated.
Dinesh Kannab Reviewed on :15 Mar 2025
Everything is very good , well planned and cab drivers are very friendly
Dinesh Kannab Reviewed on :15 Mar 2025
Everything is very good , well planned and cab drivers are very friendly
Shaheda Tabassum Reviewed on :14 Mar 2025
We are so glad that we chose PYT to plan our honeymoon trip to Maldives in the month of December 2024. Browsing through instagram one day, I suddenly came across a reel from PYT regarding Maldives. I browsed vlog pages and YouTube channels for honest reviews regarding it since it was quite unknown here in Kolkata. A leap of faith made me sign in to the app and the rest is history. Right from customising the Maldives trip during peak season (se went during the New Year time, the peakest season ever) within our budget to providing expert opinions and 24*7 WhatsApp support, PYT ensured that the entire process was completely hassle free. They even included luxurious add-ons for us as part of complimentary honeymoon inclusions. We stayed in the premium Reethi Faru Island Resort with both ways seaplane transfers and staycation in both deluxe jacuzzi pool villa and overwater sunset villa along with halfboard meal plan with elaborate buffets. The 4 days trip was nothing short of magical for us and that too without burning a hole in our pockets. Thank you so much PYT for not letting by blind trust and leap of faith go in vain. HIGHLY RECOMMEND IT FOR MEMORABLE TRIPS!!
+1View all
Shaheda Tabassum Reviewed on :14 Mar 2025
We are so glad that we chose PYT to plan our honeymoon trip to Maldives in the month of December 2024. Browsing through instagram one day, I suddenly came across a reel from PYT regarding Maldives. I browsed vlog pages and YouTube channels for honest reviews regarding it since it was quite unknown here in Kolkata. A leap of faith made me sign in to the app and the rest is history. Right from customising the Maldives trip during peak season (se went during the New Year time, the peakest season ever) within our budget to providing expert opinions and 24*7 WhatsApp support, PYT ensured that the entire process was completely hassle free. They even included luxurious add-ons for us as part of complimentary honeymoon inclusions. We stayed in the premium Reethi Faru Island Resort with both ways seaplane transfers and staycation in both deluxe jacuzzi pool villa and overwater sunset villa along with halfboard meal plan with elaborate buffets. The 4 days trip was nothing short of magical for us and that too without burning a hole in our pockets. Thank you so much PYT for not letting by blind trust and leap of faith go in vain. HIGHLY RECOMMEND IT FOR MEMORABLE TRIPS!!
+1View all
Sanket Kasar Reviewed on :14 Mar 2025
Pickyourtrails services are very professional. They understand your requirements and plan everything within your budget. The best part is the flexibility and variety that they provide in planning the itinerary and activities. Also the continuous support, especially the 24x7 online support while on trip is really commendable. I would recommend Pickyourtrail for all types of trips, especially international trips, and also urge the team at Pickyourtrail to keep up the great work! Kudos to the team!
Sanket Kasar Reviewed on :14 Mar 2025
Pickyourtrails services are very professional. They understand your requirements and plan everything within your budget. The best part is the flexibility and variety that they provide in planning the itinerary and activities. Also the continuous support, especially the 24x7 online support while on trip is really commendable. I would recommend Pickyourtrail for all types of trips, especially international trips, and also urge the team at Pickyourtrail to keep up the great work! Kudos to the team!
Santosh Kumar Nayak Reviewed on :14 Mar 2025
Trip was awesome and seamless. It was all well managed and hotel accomodation was also very good. Hotel staff was very polite and respectful Hotel buffet spread was large one and very good
Santosh Kumar Nayak Reviewed on :14 Mar 2025
Trip was awesome and seamless. It was all well managed and hotel accomodation was also very good. Hotel staff was very polite and respectful Hotel buffet spread was large one and very good
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