Embark on an unforgettable journey to Chicago, where breathtaking landscapes, vibrant culture, and rich history await you. Whether you’re exploring iconic landmarks, indulging in local cuisine, or unwinding in luxury resorts, Chicago offers a diverse experience for every traveler. From the bustling streets of its cities to tranquil escapes in nature, this destination promises something for everyone. Get ready to immerse yourself in the unique beauty and charm of Chicago, a place that blends tradition with modernity in the most captivating way.

Why Book with Pickyourtrail?

Planning a trip can be overwhelming, but with the right travel partner, your dream Chicago vacation can be seamless and hassle-free. That’s where Pickyourtrail comes in. Crafting personalised itineraries that cater to your travel style and preferences.

Tailor-Made Itineraries: With Pickyourtrail, you get fully customised travel plans that match your preferences, budget, and schedule.
Hassle-Free Planning: We take care of everything, from visa processing and flights to accommodations and local transfers.
Exclusive Deals & Best Prices: Enjoy the best rates on flights, hotels, and experiences, ensuring great value for your trip with us.
24/7 On-Trip Assistance: You will get to travel with peace of mind knowing our team is available around the clock to support you.
Seamless Digital Experience: Use our smart travel app to access itineraries, bookings, and real-time updates.
Authentic Local Experiences: Immerse yourself in unique activities, from cultural tours to adventure sports, making your trip unforgettable.

Book your dream Chicago vacation with Pickyourtrail today and embark on a journey like never before!

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

Hotels

8 activities

Shared transfer

24x7 concierge

AED 10,229

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

Hotels

8 activities

Shared transfer

24x7 concierge

AED 10,229

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

Love from our travellers

Arpana Devarhubli

Reviewed on :07 Oct 2024

Arpana Devarhubli

Reviewed on :07 Oct 2024

Beautiful 14 day USA itinerary for the Solo travellers

13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5

Hotels

8 activities

Shared transfer

24x7 concierge

AED 10,196

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

Hotels

8 activities

Shared transfer

24x7 concierge

AED 6,517

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

Hotels

7 activities

Shared transfer

24x7 concierge

AED 9,044

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

Hotels

6 activities

Shared transfer

24x7 concierge

AED 8,089

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

Hotels

7 activities

Shared transfer

24x7 concierge

AED 10,286

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

Hotels

7 activities

Shared transfer

24x7 concierge

AED 8,512

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

Hotels

8 activities

Shared transfer

24x7 concierge

AED 8,155

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

Hotels

6 activities

Shared transfer

24x7 concierge

AED 4,376

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,036

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,036

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,036

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 3,883

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,140

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,140

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,140

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,140

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,140

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 5,140

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 4,143

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 4,143

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 4,143

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 4,143

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 4,143

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

Hotels

5 activities

Shared transfer

24x7 concierge

AED 3,847

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

Hotels

4 activities

Shared transfer

24x7 concierge

AED 4,143

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

Hotels

5 activities

Shared transfer

24x7 concierge

AED 4,305

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

Hotels

5 activities

Shared transfer

24x7 concierge

AED 5,315

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

Hotels

10 activities

Shared transfer

24x7 concierge

AED 7,273

per person

Macy's Center City History Tour in Philadelphia

+ 9 more

Usa City Packages

Las Vegas Tour PackagesAED 75,262/Person

Miami Tour PackagesAED 92,439/Person

New York Tour PackagesAED 75,262/Person

San Francisco Tour PackagesAED 107,912/Person

Chicago Tour PackagesAED 75,262/Person

Orlando Tour PackagesAED 107,178/Person

Boston Tour PackagesAED 127,797/Person

Los Angeles Tour PackagesAED 75,262/Person

Atlanta Tour PackagesAED 124,768/Person

Orlando Tour PackagesAED 107,178/Person

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Reviews from Usa travellers

Arpana Devarhubli

Reviewed on :07 Oct 2024

Arpana Devarhubli

Reviewed on :07 Oct 2024

Sai Pavan Pdv

Reviewed on :21 Mar 2025

We went to Bali through Pickyourtrail and The trip was organized well. But I was only disappointed when they charged extra for 1 hour in a day as there was lot of queue at the temple place. I have paid 1.3 Lakhs IDR for this 1 hour. They should anticipate the delay and schedule the package, but sometimes a 1 hr delay might happen which is common in any travel. Except this the remaining things were all good from Pickyourtrail

Sai Pavan Pdv

Reviewed on :21 Mar 2025

Arunkumar A

Reviewed on :21 Mar 2025

We are very happy with the end to end arrangements and services provided by pickyourtrail team. It made our trip tobali memorable. Looking forward to book again with pickyourtrail

Arunkumar A

Reviewed on :21 Mar 2025

We are very happy with the end to end arrangements and services provided by pickyourtrail team. It made our trip tobali memorable. Looking forward to book again with pickyourtrail

Aditi Nain

Reviewed on :21 Mar 2025

Had a awesome trip to Malaysia for our son's first birthday. Thanks to pickyourtrail and special thanks to Mr. Faizan Khan for making our trip memorable and planing the itinerary according to our needs. Excellent arrangement, very friendly and helpful team with good quality of service.

+1View all

Aditi Nain

Reviewed on :21 Mar 2025

+1View all

Muthu Kumar

Reviewed on :21 Mar 2025

Overall experience in Bali is good. I would like to thank hariharan and team for make this trip possible in a very short time interval. Also, the local guide Beni was too good with us. 100% safety for family. Checkout time on hotel residency could be made according to the flight timing, because I have paid extra for an hour myself as my flight timing didn't match with checkout time. Other than that everything is cool. Thanks

Muthu Kumar

Reviewed on :21 Mar 2025

Diwaakar Diwa

Reviewed on :21 Mar 2025

The service is really good, but bit expensive compared to others

Diwaakar Diwa

Reviewed on :21 Mar 2025

The service is really good, but bit expensive compared to others

Amrender Singh

Reviewed on :21 Mar 2025

Amazing service, customer service, absolutely amazing experience 5 stars and highly recommended to go with Pick your trail - Sunny was amazing in bus service and Siyam world Maldives property was definitely worth every penny

Amrender Singh

Reviewed on :21 Mar 2025

Komaravel K

Reviewed on :21 Mar 2025

We had an amazing holiday in Bali. Thanks to Pickyourtrail. They helped us to customize the itinerary to match our preferences perfectly. Team in Bali was incredibly supportive. The driver and guide were very helpful, ensuring a smooth experience throughout our trip.

Komaravel K

Reviewed on :21 Mar 2025

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

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