Chicago Trip PackagesExperience big cities, diverse landscapes and melting pot of culture
4.2 from 552 travellers
Chicago Trip Packages
IDEAL DURATION4 nights
STARTING PRICEAED 4,443
OUR EXPERTISE
4.2from 552 travellers
  1. Packages
  2. Chicago Trip Packages

Chicago Tour Packages

The fun doesn't just stop Here. The wanderlust in you is bound to augment once you check out our various theme based packages for other destinations like New Zealand, Europe, and Australia. Planning to take a family vacation or set out on an adventurous holiday with your friends? We have customisable packages catering to them as well. All you need to do is let us know your interests and preferences; and your holiday package is ready to go.
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13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5
Hotels
8 activities
Shared transfer
24x7 concierge
AED 10,385
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5
Hotels
8 activities
Shared transfer
24x7 concierge
AED 10,385
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
13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5
Hotels
8 activities
Shared transfer
24x7 concierge
AED 10,352
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5
Hotels
8 activities
Shared transfer
24x7 concierge
AED 6,617
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
7 activities
Shared transfer
24x7 concierge
AED 9,182
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
13 nights:

Chicago (3N)

Washington D.C (2N)

+4 Cities

4.5
Hotels
6 activities
Shared transfer
24x7 concierge
AED 8,212
per person
  • Macy's Center City History Tour in Philadelphia
+ 5 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
7 activities
Shared transfer
24x7 concierge
AED 10,443
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
7 activities
Shared transfer
24x7 concierge
AED 8,642
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 6 more
13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5
Hotels
8 activities
Shared transfer
24x7 concierge
AED 8,279
per person
  • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
+ 7 more
13 nights:

Chicago (3N)

Washington D.C (3N)

+3 Cities

4.5
Hotels
6 activities
Shared transfer
24x7 concierge
AED 4,442
per person
  • Macy's Center City History Tour in Philadelphia
+ 5 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,113
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,113
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,113
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 3,942
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,218
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,218
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,218
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,218
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,218
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 5,218
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 4,207
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 4,207
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 4,207
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 4,207
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 4,207
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
5 activities
Shared transfer
24x7 concierge
AED 3,905
per person
  • Macy's Center City History Tour in Philadelphia
+ 4 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
4 activities
Shared transfer
24x7 concierge
AED 4,207
per person
  • Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
5 activities
Shared transfer
24x7 concierge
AED 4,371
per person
  • Macy's Center City History Tour in Philadelphia
+ 4 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
5 activities
Shared transfer
24x7 concierge
AED 5,396
per person
  • Macy's Center City History Tour in Philadelphia
+ 4 more
10 nights:

Chicago (2N)

Washington D.C (2N)

+3 Cities

4.5
Hotels
10 activities
Shared transfer
24x7 concierge
AED 7,384
per person
  • Macy's Center City History Tour in Philadelphia
+ 9 more
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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
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