Best Chicago Last Minute Deals*

*Some taxes, fees extra. Vacation & cruise rates are per person with double occupancy, unless noted.
$158* & up -- Flights from Chicago on American, R/T
Source: American Airlines | By Travelzoo Staff

This nationwide sale features fares to/from major US cities including NYC, Miami, Los Angeles and Chicago
Travel through June 7, book by April 24

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Source: Porter Airlines

Snag a deal on summer travel aboard award-winning Porter Airlines, where in-flight benefits include free wine, beer, snacks and soft drinks.
Travel through Sept. 3

 
Source: Trump International Hotel & Tower Chicago

Luxuriate at a downtown Chicago hotel with show-stopping views and a long list of awards, including Travel + Leisure’s World’s Best.
Select dates through July 8

 
Source: Apple Vacations

Relax at this all-suite resort with spectacular bay and mountain views and receive daily complimentary green fees.
Select departures June-July

 
Source: Toronto Escapes

Visit Toronto, where the newly opened Ripley's aquarium joins popular attractions like the CN Tower Edge Walk and baseball games at the Rogers Centre.
Select dates May 14 - June 22; book by April 28

 
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 8

 
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: 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 Oct. 4

 
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: Virgin America

Book a flight on Conde Nast Traveler's 'Best Domestic Airline'
May 13 - June 11

 
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 May 14 - June 26; book by April 30

 

Latest Sales & Specials*

 
Next Two Weekends
Major Airlines on Fly.com
 
 
Travel through July; Book by April 24
SmartFares
 
Select May-June departures
Apple Vacations
 
 
 
Select dates through December; varies by route
LAN
 
 
 
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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Travelzoo Tips

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