pickyourtrail_logo
Chicago Trip Packages
No of Days
Hotel Ratings
Budget
Need help? Talk to an expert
  2. Packages
  3. Chicago Trip Packages

Chicago Vacation Packages From USA

Ideal durations
4 nights
best time
Apr- May
Price starts at$ 932/person
Visa processing
30 days
TRAVELLER RATINGS

4.2 from 552 travellers

Incredible 14 day USA itinerary for the Solo travellers

Incredible 14 day USA itinerary for the Solo travellers

  • Chicago (3N)
  • Washington D.C (3N)
+3 cities
  • Attraction
  • Leisure
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Adler Planetarium and Astronomy Museum
    • Big Bus Washington DC Hop-On Hop-Off Tour +5 activities
    Inclusions (customisable)
    • Hotels
    • 8 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,866 /Person

    A 13 night trip to incredible USA

    A 13 night trip to incredible USA

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Attraction
  • Leisure
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Adler Planetarium and Astronomy Museum
    • Big Bus Washington DC Hop-On Hop-Off Tour +5 activities
    Inclusions (customisable)
    • Hotels
    • 8 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,866 /Person

    Beautiful 14 day USA itinerary for the Solo travellers

    Beautiful 14 day USA itinerary for the Solo travellers

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Leisure
  • Attraction
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Adler Planetarium and Astronomy Museum
    • Big Bus Washington DC Hop-On Hop-Off Tour +5 activities
    Inclusions (customisable)
    • Hotels
    • 8 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,857 /Person

    A Honeymoon itinerary: A fantastic 13 night USA trip

    A Honeymoon itinerary: A fantastic 13 night USA trip

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Leisure
  • Attraction
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Adler Planetarium and Astronomy Museum
    • Big Bus Washington DC Hop-On Hop-Off Tour +5 activities
    Inclusions (customisable)
    • Hotels
    • 8 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,827 /Person

    10 nights 11 days Incredible United States of America attraction Solo Holiday Package

    10 nights 11 days Incredible United States of America attraction Solo Holiday Package

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Kid_friendly
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Big Bus Washington DC Hop-On Hop-Off Tour
    • National Gallery of Art: Religious Art Tour +4 activities
    Inclusions (customisable)
    • Hotels
    • 7 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,534 /Person

    The perfect 14 day USA itinerary for the adventure lovers

    The perfect 14 day USA itinerary for the adventure lovers

    • Chicago (3N)
    • Washington D.C (2N)
    +4 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Driehaus Museum Admission +3 activities
    Inclusions (customisable)
    • Hotels
    • 6 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,267 /Person

    A Solo itinerary: A fantastic 13 night USA trip

    A Solo itinerary: A fantastic 13 night USA trip

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Leisure
  • Attraction
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Adler Planetarium and Astronomy Museum
    • Big Bus Washington DC Hop-On Hop-Off Tour +5 activities
    Inclusions (customisable)
    • Hotels
    • 8 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,285 /Person

    Art lover's holiday: Lose yourself in amazing USA

    Art lover's holiday: Lose yourself in amazing USA

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Driehaus Museum Admission +3 activities
    Inclusions (customisable)
    • Hotels
    • 6 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,226 /Person

    Ideal United States of America Honeymoon trip

    Ideal United States of America Honeymoon trip

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,411 /Person

    10 nights 11 days Relaxing United States of America attraction Honeymoon trip

    10 nights 11 days Relaxing United States of America attraction Honeymoon trip

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,411 /Person

    Incredible United States of America Couple Package

    Incredible United States of America Couple Package

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,411 /Person

    Honeymoon special: ideal 10 night trip to USA

    Honeymoon special: ideal 10 night trip to USA

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,088 /Person

    Kindling the beautiful in you : A perfect USA itinerary

    Kindling the beautiful in you : A perfect USA itinerary

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    An epic 10 night USA itinerary for the incredible

    An epic 10 night USA itinerary for the incredible

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    Lovely United States of America Honeymoon package from India

    Lovely United States of America Honeymoon package from India

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    Amazing 11 day trip to USA for Honeymoon

    Amazing 11 day trip to USA for Honeymoon

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    Rejuvenating 11 day USA itinerary for the Honeymoon travellers

    Rejuvenating 11 day USA itinerary for the Honeymoon travellers

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    The best itinerary to explore the amazing side of USA

    The best itinerary to explore the amazing side of USA

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    A 10 night trip to ideal USA

    A 10 night trip to ideal USA

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,440 /Person

    Relaxing United States of America Honeymoon trip

    Relaxing United States of America Honeymoon trip

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,161 /Person

    Beautiful United States of America Tour Package for Couple

    Beautiful United States of America Tour Package for Couple

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,161 /Person

    Incredible 11 day USA itinerary for the Honeymoon travellers

    Incredible 11 day USA itinerary for the Honeymoon travellers

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,161 /Person

    Amazing United States of America Package for Couple

    Amazing United States of America Package for Couple

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,161 /Person

    A 10 night trip to awesome USA

    A 10 night trip to awesome USA

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,161 /Person

    Incredible 10 night USA itinerary

    Incredible 10 night USA itinerary

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +2 activities
    Inclusions (customisable)
    • Hotels
    • 5 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,078 /Person

    Beautiful 11 day USA itinerary for the Honeymoon travellers

    Beautiful 11 day USA itinerary for the Honeymoon travellers

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Big Bus Washington DC Hop-On Hop-Off Tour +1 activities
    Inclusions (customisable)
    • Hotels
    • 4 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,161 /Person

    Ideal itinerary for the best Solo vacation to USA

    Ideal itinerary for the best Solo vacation to USA

    • Chicago (3N)
    • Washington D.C (2N)
    +3 cities
  • Leisure
  • Attraction
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Driehaus Museum Admission +3 activities
    Inclusions (customisable)
    • Hotels
    • 6 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,769 /Person

    10 nights 11 days Relaxing United States of America leisure Honeymoon trip

    10 nights 11 days Relaxing United States of America leisure Honeymoon trip

    • Chicago (2N)
    • Washington D.C (2N)
    +3 cities
  • Kid_friendly
  • Attraction
    • 360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
    • Big Bus Washington DC Hop-On Hop-Off Tour
    • National Gallery of Art: Religious Art Tour +3 activities
    Inclusions (customisable)
    • Hotels
    • 6 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,652 /Person

    An incredible 14 day USA itinerary for an unforgettable Solo vacation

    An incredible 14 day USA itinerary for an unforgettable Solo vacation

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Driehaus Museum Admission +3 activities
    Inclusions (customisable)
    • Hotels
    • 6 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 2,367 /Person

    A 14 day itinerary for a feel-good USA vacation

    A 14 day itinerary for a feel-good USA vacation

    • Chicago (3N)
    • Washington D.C (3N)
    +3 cities
  • Attraction
  • Leisure
    • Macy's Center City History Tour in Philadelphia
    • Chicago World's Fair of 1893 Walking Tour
    • Driehaus Museum Admission +3 activities
    Inclusions (customisable)
    • Hotels
    • 6 activities
    • Transfers
    • 24x7 concierge

    Starts from$ 1,715 /Person

    Usa Packages By Cities

    New York Tour Packages
    $ 87,090/person
    Las Vegas Tour Packages
    $ 87,090/person
    Los Angeles Tour Packages
    $ 87,090/person
    Boston Tour Packages
    $ 1,27,797/person
    Orlando Tour Packages
    $ 92,439/person
    Miami Tour Packages
    $ 92,439/person
    San Francisco Tour Packages
    $ 1,07,912/person
    View All
    + 5 More
    New York Tour Packages
    $ 87,090/person
    Las Vegas Tour Packages
    $ 87,090/person
    Los Angeles Tour Packages
    $ 87,090/person
    Boston Tour Packages
    $ 1,27,797/person
    Orlando Tour Packages
    $ 92,439/person
    Miami Tour Packages
    $ 92,439/person
    San Francisco Tour Packages
    $ 1,07,912/person
    View All
    + 5 More
    Customise and build your own itinerary
    Create Now

    We think you are in .
    Update your location?