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Chicago Trip PackagesExperience big cities, diverse landscapes and melting pot of culture
4.2 from 552 travellers
Chicago Trip Packages
IDEAL DURATION4 nights
STARTING PRICE₹99,062
OUR EXPERTISE
4.2from 552 travellers
  2. Packages
  3. Chicago Trip Packages

Chicago Tour Packages

Let’s enrich ourselves in Chicago and explore its landmarks and cultural life with one of the luxurious Chicago holiday packages available on PickYourTrail. Through this package, tourists can visit some of the most famous attractions, such as Willis Tower, Millennium Park, and the Art Institute of Chicago.

Chicago could hardly be enumerated among the sights themselves, but it's worth mentioning its specialties like deep-dish pizza, jazz, and the lakefront. As one of the biggest cities in the United States, Chicago offers many things, from the best museums to amazing culinary experiences. All of it can be booked with the PickYourTrail Chicago luxury holiday package. Plan your wanderlust at PickYourTrail and explore more of the Windy City with our Chicago tour package.

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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
Hotels
8 activities
Shared transfer
24x7 concierge
₹231,582
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
₹231,582
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
Love from our travellersView all
Customer 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
Customer 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
Love from our travellers
Customer 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
Customer 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
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
₹230,838
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
₹147,551
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
₹204,756
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
Not sure where to travel?Talk to our travel experts and get a package based on your personal preferences.
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
₹183,120
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
₹232,877
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
₹192,706
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
₹184,616
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
₹99,061
per person
  • Macy's Center City History Tour in Philadelphia
+ 5 more
Not sure where to travel?Talk to our travel experts and get a package based on your personal preferences.
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
₹114,007
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
₹114,007
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
₹114,007
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
₹87,912
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
₹116,358
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
Not sure where to travel?Talk to our travel experts and get a package based on your personal preferences.
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
₹116,358
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
Lovely United States of America Honeymoon package from India
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
₹116,358
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
₹116,358
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
₹116,358
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
₹116,358
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
Not sure where to travel?Talk to our travel experts and get a package based on your personal preferences.
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
₹116,358
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
₹93,804
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
₹93,804
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
₹93,804
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
₹93,804
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
Not sure where to travel?Talk to our travel experts and get a package based on your personal preferences.
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
₹93,804
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
₹87,089
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
₹93,804
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
₹97,467
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
₹120,325
per person
  • Macy's Center City History Tour in Philadelphia
+ 4 more
Not sure where to travel?Talk to our travel experts and get a package based on your personal preferences.
Usa City Packages
New York Tour Packages
New York Tour Packages₹75,262/Person
Las Vegas Tour Packages
Las Vegas Tour Packages₹75,262/Person
Los Angeles Tour Packages
Los Angeles Tour Packages₹75,262/Person
Boston Tour Packages
Boston Tour Packages₹127,797/Person
Orlando Tour Packages
Orlando Tour Packages₹92,439/Person
Miami Tour Packages
Miami Tour Packages₹92,439/Person
San Francisco Tour Packages
San Francisco Tour Packages₹107,912/Person
Chicago Tour Packages
Chicago Tour Packages₹75,262/Person
Atlanta Tour Packages
Atlanta Tour Packages₹124,768/Person
Orlando Tour Packages
Orlando Tour Packages₹92,439/Person
Customer 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
Customer 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
Usa City Packages
New York Tour Packages
Las Vegas Tour Packages
Los Angeles Tour Packages
Boston Tour Packages
Orlando Tour Packages
Miami Tour Packages
San Francisco Tour Packages
Chicago Tour Packages
Atlanta Tour Packages
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