Best Chicago Last Minute Deals*

*Some taxes, fees extra. Vacation & cruise rates are per person with double occupancy, unless noted.
$149* & up -- Nationwide Chicago Fares in Spring, One Way
Source: Virgin America | By Travelzoo Staff

Book a flight on Conde Nast Traveler's 'Best Domestic Airline'
May 6 -June 18

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Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.
Select dates through July 3

 
Source: The Westin Chicago River North

Check in to a AAA 4-Diamond hotel with a top location and sweeping views of the Chicago river.
Select dates through Aug. 29

 
Source: Apple Vacations

Kick back at a pristine all-suite 'Dreams' resort with unlimited meals and drinks, including alcohol
Select May-October dates

 
Source: Trump International Hotel & Tower Chicago

Luxuriate at a 5-star downtown hotel with show-stopping views and a long list of awards, including 'World's Best'
Select dates through July 8

 
Source: Hilton Chicago O'Hare

Make flying into and out of the Windy City a breeze with this bed & breakfast package
Weekends in May; +$20 Weekends in April

 
Source: LAN

Discounted flights to Buenos Aires, Bariloche, Cordoba, Mendoza and more
Select dates through December; varies by route

 
Source: Sheraton Chicago Hotel & Towers

Take in top city sights and skyline views from a 4-star Chicago hotel.
Select dates through Sept. 1

 
Source: Apple Vacations

Two children stay free during select dates at this all-inclusive resort located on a white-sand beach dotted with swaying palm trees.
Select departures in May

 
Source: Lufthansa

Travel to cities throughout Europe with special fares from a 4-star airline
Depart May 16-29

 
Source: Air Canada

Take advantage of the strong U.S. dollar with a trip north of the border. Fly Air Canada where in-flight benefits include free on-demand movies & TV.
Select dates through 2014; varies by route

 
Source: LatinEscapes.com

This package includes tours of Lima, Machu Pichu, Cuzco, and nearby ruins
Select dates through December 2014

 

Latest Sales & Specials*

 
 
Select May-June departures
Apple Vacations
 
 
Travel through June; Book by April 25
SmartFares
 
Travel through June; Book by April 25
SmartFares
 
 
Next Two Weekends
Major Airlines on Fly.com
 
Select dates through December; varies by route
LAN
 
Select dates through April 22
Toronto Escapes
 
 
Select dates through 2014; varies by route
Air Canada
 
 
 
Select dates through November, 2014
LatinEscapes.com
 
Select dates through November, 2014
LatinEscapes.com
 
Select dates through November 2014
LatinEscapes.com
 
Select dates through November, 2014
LatinEscapes.com
 
Select dates thru April 2015
PacificIslands.com
 
Select dates thru April 2015
PacificIslands.com
 

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DOT Full Fare Rules

New U.S. government rules require airfare and air-inclusive packages to include all taxes and fees in the price. Learn More

Travelzoo Tips

Heidi Stallings — Travel, Entertainment and Local Deal Expert
Heidi Stallings
Deal Expert, Chicago
Embrace the season and enjoy a wintry weekend. More