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 $325 just by booking your flight and hotel together. 
  • Save up to $325 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
Hilton Chicago
4 Star
720 South Michigan Avenue
Chicago, Illinois
photos | amenities | guest reviews
flight + 2 night hotel from
$516 pp
book Hilton Chicago
price shown departs from Phoenix
The Hilton Chicago hotel is a landmark downtown Chicago hotel located on the *Cultural Michigan Avenue Mile* overlooking Grant Park Lake Michigan and Museum Campus. It is the close... read more
Hilton Chicago O' Hare Airport
Hilton Chicago O' Hare Airport
4 Star
O Hare International Airport
Chicago, Illinois
photos | amenities | guest reviews
flight + 3 night hotel from
$439 pp
book Hilton Chicago O' Hare Airport
price shown departs from Memphis
The Hilton Chicago O*Hare Airport hotel is a 3-Star 3-Diamond property ideally located in the heart of O*Hare International Airport. No need to worry about those early morning flig... read more
The Palmer House Hilton
The Palmer House Hilton
4 Star
17 East Monroe Street
Chicago, Illinois
photos | amenities | guest reviews
flight + 5 night hotel from
$639 pp
book The Palmer House Hilton
price shown departs from New York City
The Palmer House Hilton - The Chicago Hotel The World Knows Best Welcome to The Palmer House a Hilton Hotel - an iconic world-class downtown Chicago hotel and gateway to Chicago*s ... read more
Millennium Knickerbocker Hotel Chicago
Millennium Knickerbocker Hotel Chicago
4 Star
163 East Walton Place
Chicago, Illinois
photos | amenities | guest reviews
flight + 7 night hotel from
$809 pp
book Millennium Knickerbocker Hotel Chicago
price shown departs from San Diego
A landmark hotel located at the gateway to Chicago's famed Magnificent Mile, the historic Knickerbocker welcomes you to the best destination in downtown Chicago for shopping, dinin... read more
Crowne Plaza Chicago O Hare Hotel And Conference Center
Crowne Plaza Chicago O Hare Hotel And Conference Center
3.5 Star
5440 North River Road
Rosemont, Illinois
photos | amenities | guest reviews
flight + 5 night hotel from
$478 pp
book Crowne Plaza Chicago O Hare Hotel And Conference Center
price shown departs from New York City
New in 2009 - Brand New Guest Rooms and Suites! Located just 1.5 miles from O'Hare International Airport (ORD), the Crowne Plaza Chicago O'Hare is a hotel of remarkable value. All... read more

More Chicago Vacation Packages*

Candlewood Suites Chicago O' Hare
price shown departs from Minneapolis
2 Star
flight + 3 night hotel from
$199 pp
go to Candlewood Suites Chicago O' Hare
Radisson Hotel Chicago O' Hare
price shown departs from Los Angeles
3 Star
flight + 4 night hotel from
$489 pp
go to Radisson Hotel Chicago O' Hare

price drop

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


Swissotel Chicago
price shown departs from New York City
4 Star
flight + 5 night hotel from
$593 pp
go to Swissotel Chicago
The Tremont Hotel
price shown departs from New Orleans
2.5 Star
flight + 2 night hotel from
$328 pp
go to The Tremont Hotel
Holiday Inn Chicago North Shore Skokie
price shown departs from Washington
3 Star
flight + 4 night hotel from
$258 pp
go to Holiday Inn Chicago North Shore Skokie

price drop

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


The Drake
price shown departs from Baltimore
4 Star
flight + 3 night hotel from
$692 pp
go to The Drake
Club Quarters Wacker At Michigan
price shown departs from Raleigh
3.5 Star
flight + 3 night hotel from
$305 pp
go to Club Quarters Wacker At Michigan

price drop

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


Club Quarters Central Loop Chicago
price shown departs from New Orleans
3 Star
flight + 2 night hotel from
$340 pp
go to Club Quarters Central Loop Chicago
W Hotel Chicago City Center
price shown departs from Albany
4 Star
flight + 4 night hotel from
$630 pp
go to W Hotel Chicago City Center
Howard Johnson Inn Downtown Chicago
price shown departs from Manchester
1 Star
flight + 2 night hotel from
$367 pp
go to Howard Johnson Inn Downtown Chicago
Hyatt Regency O Hare
price shown departs from Detroit
4 Star
flight + 3 night hotel from
$251 pp
go to Hyatt Regency O Hare
Hotel Allegro Chicago, A Kimpton Hotel
price shown departs from Great Falls
3.5 Star
flight + 3 night hotel from
$605 pp
go to Hotel Allegro Chicago, A Kimpton Hotel
Hilton Suites Chicago/Magnificent Mile
price shown departs from Rochester
3.5 Star
flight + 2 night hotel from
$210 pp
go to Hilton Suites Chicago/Magnificent Mile
Super 8 Chicago Northlake Ohare South
price shown departs from Dallas
1 Star
flight + 5 night hotel from
$473 pp
go to Super 8 Chicago Northlake Ohare South
Embassy Suites Hotel Chicago Downtown
price shown departs from Raleigh
3.5 Star
flight + 3 night hotel from
$395 pp
go to Embassy Suites Hotel Chicago Downtown

price drop

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


The Fairmont Chicago
price shown departs from Minneapolis
4 Star
flight + 3 night hotel from
$334 pp
go to The Fairmont Chicago
Seneca Hotel And Suites
price shown departs from Minneapolis
2.5 Star
flight + 4 night hotel from
$476 pp
go to Seneca Hotel And Suites
Hotel Blake Chicago
price shown departs from Detroit
3.5 Star
flight + 3 night hotel from
$275 pp
go to Hotel Blake Chicago
Hyatt Regency Mccormick Place
price shown departs from New Orleans
4 Star
flight + 2 night hotel from
$336 pp
go to Hyatt Regency Mccormick Place
Best Western Chicagoland - Countryside
price shown departs from Salt Lake City
2 Star
flight + 3 night hotel from
$375 pp
go to Best Western Chicagoland - Countryside

price drop

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


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*You can save up to $325 when you use priceline.com's Vacation Package service to book your hotel and flight together. The savings figure is based on an internal study comparing the price for travel for two passengers of booking a flight and hotel together using priceline.com's Vacation Packages to booking the same hotel and similar flight itinerary (same travel dates and origin and destination cities) separately on priceline.com. The Vacation Package price yielded a savings of up to $325 over the separate prices of the same hotel and similar flight itinerary. Vacation Package prices shown are per-person based on double occupancy, include round-trip airfare and hotel, and all taxes and fees. Vacation Package prices shown are based on availability over the last 21 days. There is no guarantee that Vacation Package hotels or prices will be available. Requests for same-day travel must be submitted prior to 12:00 PM local time in your departure city. See website for additional details.
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