Chicago

CHICAGO
VACATION PACKAGE DEALS

Whether you're looking down from the awesome height of the Sears Tower observation deck or the slightly lower vantage point of the Ferris Wheel at Navy Pier, Chicago is a thrilling city with something for everybody to see! Shop and compare Chicago Vacation Package deals at priceline and save up to $500 just by booking your flight and hotel together. 
  • Save up to $500 when you book your hotel & flight together
  • Choose Your Exact Hotel + See pictures and descriptions
  • Choose Your Exact Flight + See airlines and times

Chicago Vacation Package Deals *

Hilton Chicago
4 Star
720 South Michigan Avenue
Chicago, Illinois
photos | amenities | guest reviews
flight + 3 night hotel from
$578 pp
price shown departs from Newark
Located on Michigan Avenue overlooking Grant Park and Lake Michigan, the magnificent Hilton Chicago offers guests a beautiful lakeside, metropolitan setting in the center of Chicag... read more
The Palmer House Hilton
4 Star
17 East Monroe Street
Chicago, Illinois
photos | amenities | guest reviews
flight + 3 night hotel from
$632 pp
price shown departs from Atlanta
The Chicago Hotel the World Knows Best! Palmer House Hilton hotel guests enjoy close proximity to the Art Institute of Chicago, Grant Park, Millennium Park and Navy Pier. State Str... read more
Hilton Chicago O' Hare Airport
4 Star
O Hare International Airport
Chicago, Illinois
photos | amenities | guest reviews
flight + 3 night hotel from
$546 pp
price shown departs from Houston
The Hilton Chicago O'Hare Airport has the unique advantage of being the only hotel located on the grounds of the Chicago's O'Hare International Airport. The 858 room, ten story hot... read more
Millennium Knickerbocker Hotel Chicago
4 Star
163 East Walton Place
Chicago, Illinois
photos | amenities | guest reviews
flight + 3 night hotel from
$381 pp
price shown departs from Minneapolis
A landmark on North Michigan Avenue, the famous Magnificent Mile, this hotel welcomes you to the best location in the city for shopping, dining and business. European style and gra... read more
Sheraton Suites Elk Grove
3.5 Star
121 Northwest Point Boulevard
Elk Grove Village, Illinois
photos | amenities | guest reviews
flight + 3 night hotel from
$475 pp
price shown departs from New York City
The Sheraton Suites Elk Grove Village offers 253 suites with separate living rooms, bedrooms and dressing areas. Business and leisure travelers alike will appreciate the Sheraton's... read more

More Chicago Vacation Packages*

flight + 3 night hotel from
$417 pp

price drop

PriceDrop
PriceDrop packages prices are those that have dropped by more than 15% in the last 3 weeks.*


Radisson Hotel Chicago O Hare
price shown departs from Seattle
3 Star
flight + 3 night hotel from
$674 pp
The Tremont Chicago Hotel At Magnificent Mile
price shown departs from Cleveland
3 Star
flight + 3 night hotel from
$496 pp
Swissotel Chicago
price shown departs from Boston
4 Star
flight + 3 night hotel from
$754 pp
Holiday Inn Chicago North Shore Skokie
price shown departs from Phoenix
3 Star
flight + 3 night hotel from
$464 pp
The Drake Hotel
price shown departs from Philadelphia
4 Star
flight + 3 night hotel from
$571 pp

price drop

PriceDrop
PriceDrop packages prices are those that have dropped by more than 15% in the last 3 weeks.*


Club Quarters Wacker At Michigan
price shown departs from San Francisco
3.5 Star
flight + 5 night hotel from
$849 pp
Club Quarters Central Loop Chicago
price shown departs from Washington
3.5 Star
flight + 3 night hotel from
$484 pp

price drop

PriceDrop
PriceDrop packages prices are those that have dropped by more than 15% in the last 3 weeks.*


W Hotel Chicago City Center
price shown departs from Washington
4 Star
flight + 3 night hotel from
$589 pp

price drop

PriceDrop
PriceDrop packages prices are those that have dropped by more than 15% in the last 3 weeks.*


Hyatt Regency O Hare
price shown departs from San Francisco
4 Star
flight + 3 night hotel from
$559 pp
Allegro Chicago, A Kimpton Hotel
price shown departs from Cleveland
4 Star
flight + 3 night hotel from
$470 pp

price drop

PriceDrop
PriceDrop packages prices are those that have dropped by more than 15% in the last 3 weeks.*


Hilton Chicago/Oak Lawn
price shown departs from Houston
3.5 Star
flight + 3 night hotel from
$519 pp
Fairfield Inn And Suites By Marriott Midway Airport
price shown departs from Minneapolis
2 Star
flight + 3 night hotel from
$378 pp
Fairfield Inn & Suites By Marriott Chicago Naperville
price shown departs from New York City
2.5 Star
flight + 3 night hotel from
$477 pp
The Fairmont Chicago
price shown departs from Kansas City
4 Star
flight + 3 night hotel from
$472 pp
Embassy Suites Hotel Chicago Downtown
price shown departs from Philadelphia
3.5 Star
flight + 3 night hotel from
$691 pp
Hilton Suites Chicago/Magnificent Mile
price shown departs from Phoenix
3.5 Star
flight + 3 night hotel from
$630 pp

price drop

PriceDrop
PriceDrop packages prices are those that have dropped by more than 15% in the last 3 weeks.*


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*Our travel savings are real. Some of our deepest discounts are only available when you package your flight and hotel together. The $500 savings figure is based upon recent 2011 prices including taxes and fees for two passengers booking round trip flight and hotel packages of all durations compared to booking the same flight and hotel itinerary separately on priceline.com. Individual package savings may be higher or lower based upon number of passengers, dates of travel, length of stay, origin/destination, and selected travel supplier(s).
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