Chicago Trip PackagesExperience big cities, diverse landscapes and melting pot of culture
IDEAL DURATION4 nights
STARTING PRICE$1,208
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Chicago Vacation Packages From USA
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Hotel ratings
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13 nights:
Chicago (3N)
Washington D.C (3N)
+3 Cities
4.5
Hotels8 activities
Shared transfer
24x7 concierge
$2,823
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
$2,823
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
$2,814
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
$1,799
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
$2,496
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
$2,233
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
$2,839
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
$2,349
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
$2,251
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
$1,208
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
$1,390
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
$1,390
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
$1,390
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
$1,072
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
$1,419
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
$1,419
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
$1,419
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
$1,419
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
$1,419
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
$1,419
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
$1,144
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
$1,144
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
$1,144
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
$1,144
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
$1,144
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
$1,062
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
$1,144
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
$1,188
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
$1,467
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
$2,008
per person- Macy's Center City History Tour in Philadelphia
+ 9 more
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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
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