Chicago Trip PackagesExperience big cities, diverse landscapes and melting pot of culture
IDEAL DURATION4 nights
STARTING PRICE$1,199
OUR EXPERTISE
- Packages
- Chicago Trip Packages
Chicago Vacation Packages From USA
...Read more
Budget
No of days
Hotel ratings
Thailand is now visa-free for Indian travellers - book your holiday now 
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$2,801
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
Hotels8 activities
Shared transfer
24x7 concierge
$2,801
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
13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$2,792
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
Hotels8 activities
Shared transfer
24x7 concierge
$1,785
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
Hotels7 activities
Shared transfer
24x7 concierge
$2,476
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
Hotels6 activities
Shared transfer
24x7 concierge
$2,215
per person- Macy's Center City History Tour in Philadelphia
+ 5 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels7 activities
Shared transfer
24x7 concierge
$2,816
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
Hotels7 activities
Shared transfer
24x7 concierge
$2,331
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
Hotels8 activities
Shared transfer
24x7 concierge
$2,233
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
Hotels6 activities
Shared transfer
24x7 concierge
$1,198
per person- Macy's Center City History Tour in Philadelphia
+ 5 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,379
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,379
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,379
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,063
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,407
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,407
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,407
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,407
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,407
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,407
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,134
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,134
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,134
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,134
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,134
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels5 activities
Shared transfer
24x7 concierge
$1,053
per person- Macy's Center City History Tour in Philadelphia
+ 4 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels4 activities
Shared transfer
24x7 concierge
$1,134
per person- Macy's Center City History Tour in Philadelphia
+ 3 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels5 activities
Shared transfer
24x7 concierge
$1,179
per person- Macy's Center City History Tour in Philadelphia
+ 4 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels5 activities
Shared transfer
24x7 concierge
$1,455
per person- Macy's Center City History Tour in Philadelphia
+ 4 more
10 nights:
Chicago (2N)
Washington D.C (2N)
+3 Cities
4.5
Hotels10 activities
Shared transfer
24x7 concierge
$1,991
per person- Macy's Center City History Tour in Philadelphia
+ 9 more
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$92,439/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$92,439/Person
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
Build Your Itinerary YourselfCustomise and build your own itinerary
We think you are in .
Update your location?
Update your location?