Best Chicago Last Minute Deals*

*Some taxes, fees extra. Vacation & cruise rates are per person with double occupancy, unless noted.
$2073 & up -- Costa Rica 6-Nt. Trip w/Boat Tour from Chicago
Source: Great Value Vacations | By Nile Cappello

This package includes roundtrip air, all transfers, full-day boat tour, many meals and more
Select August-December departures

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Source: American Airlines

Fly to cities nationwide including New York, Las Vegas, Austin, Miami, LA, Philadelphia and more
Select dates Aug. 25 - Dec. 17

 
Source: Multiple Travel Companies

Deals around town and nearby getaways for up to 50% off.

 
Source: Featured Destination: Puerto Rico

Save on family-friendly hotels and luxurious resorts, plus no U.S. passport is required
Through August

 
Source: Virgin America

Book a summer getaway on Conde Nast Traveler's 'Best Domestic Airline'
Aug. 19 - Oct. 29

 
Source: Grand Geneva Resort & Spa

Take the family on a Lake Geneva, Wisc., vacation this summer, complete with swims in the pool and walks along the lake.
Select dates through August

95% (65 Ratings)
 
Source: Sheraton Chicago Hotel & Towers

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

100% (2 Ratings)
 
Source: Timber Ridge Lodge & Waterpark

Slip and slide at a water park resort in Lake Geneva, Wisc., where summer rates have been discounted.
Select dates through August

100% (14 Ratings)
 
Source: Hilton Milwaukee City Center

Save nearly 60% at this ideally-located downtown hotel with historic charm
Thurs.-Sun. through Dec. 30; +$60 Mon.-Wed.

100% (8 Ratings)
 
Source: Air France

Enjoy an upgraded flight to Paris on the national air carrier of France
Travel select dates through Aug. 24

 
Source: Air France

Fly to Budapest or Paris from Chicago in late summer and early fall
Depart select dates Aug. 24 - Oct. 15

 
Source: Qatar Airways

Fly with a partner from Chicago and savor meals by celebrity chefs, lie-flat beds and thousands of entertainment options on an award-winning airline
July 22 - Aug. 31

 
Source: Medieval Times

Dine like royalty on a four-course feast and save up to 40% with this offer for the jousting and sword-fighting show at Medieval Times in Schaumburg
Valid for use through Sept. 2

97% (163 Ratings)
 
Source: Great Value Vacations

Craft a custom vacation with five nights of bed and breakfast vouchers across the Irish countryside
Select August-December departures

 
Source: Travel Discounters

Marvel at the pyramids, sail down the world's longest river, and save $580. Includes hotels, tours and most meals.
Weekly departures, Sept. 15, 2014 - Nov. 30, 2015

 

Latest Sales & Specials*

 
 
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Select August-December departures
Great Value Vacations
 
Select August-December departures
Great Value Vacations
 
Select August-December departures
Great Value Vacations
 
 

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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

Kristyn Schiavone — Travel, Entertainment and Local Deal Expert
Kristyn Schiavone
Deal Expert, Chicago
Here are some of the best values I’ve found at Navy Pier. More