Best Chicago Last Minute Deals*

*Some taxes, fees extra. Vacation & cruise rates are per person with double occupancy, unless noted.
$99 -- Chicago 4-Star Hotel on Mag Mile incl. Holidays
Source: The Gwen, A Luxury Collection Hotel | By Kelly Hickey

Starwood's first Luxury Collection hotel in Chicago is just steps from famous shops and restaurants
Travel through March 31

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Source: Club Quarters, Wacker at Michigan

Book a winter trip from just $59 per night at this boutique hotel, steps from Chicago's famed Mag Mile. Members exclusively save 25% through March.
Most dates December-February

Source: Central Loop Hotel

Get in the holiday spirit with a visit to Chi-town and the festive Christkindlmarket, located just three blocks from this hotel.
Travel most dates December-January
Travel most dates December-January

Source: State House Inn, an Ascend Collection hotel

This midcentury-modern member favorite is a great destination for a Springfield stay full of history for 50% off.
Through Feb. 29, 2016

96% (1380 ratings)
Source: The Drake Hotel

Save hundreds on a stay at the Drake, which has been on the itinerary of world leaders and international celebrities for decades.
Dec. 6 - March 4


Navigate through Dublin, Cork, Killarney and Galway with this vacation package that includes a rental car, air from Chicago and hotel accommodations
Select Nov.-Jan. dates; more dates available

Source: Lake Lawn Resort

Experience southern Wisconsin at this lakefront resort, fresh from a $4 million renovation, with an exclusive Travelzoo deal that includes weekends
Travel through February 4

95% (88 ratings)
Source: Hotel Julien

Experience historic Iowa at the elegant Hotel Julien with this Travelzoo exclusive which includes dining credit, wine tastings and more
Through March 13, 2016

Source: Alaska Airlines

The Wall Street Journal's "Middle Seat" column ranks Alaska Airlines No. 1 among all U.S. carriers in its 2014 Airline Scorecard.
Oct. 27 - Nov. 17

Source: SkyLux Travel

Additional departure dates are available starting at $50 more per person.
Through Nov. 30; Jan. 10 - March 31

Source: Lawry's The Prime Rib Chicago

Zagat rates this “gold standard” steakhouse “excellent” (26) for its signature staples like the prime rib carved tableside.
Through Nov. 30, 2015

Source: Grand Geneva Resort & Spa

Members can reserve a restorative stay at the Grand Geneva Resort, one of Wisconsin's rare AAA 4-Diamond destinations.
Sunday-Friday through March 30, 2016

Source: Timber Ridge Lodge & Waterpark

Members can reserve a night at this Chicago Tribune-praised resort -- including up to six waterpark passes -- along with a dining credit.
Sunday-Friday through March 17; +$30 for Saturdays

Source: The Westin Michigan Avenue

Deals heat up when Chicago cools down -- members can save hundreds on a stay at this 4-Diamond spot during winter months.
Most dates Dec. 13 - Feb. 6

Source: Qatar Airways

Save on fares to Abu Dhabi, Dubai, Bali, Bangkok, Singapore and more on this 5-star airline, voted Skytrax's 2015 "Airline of the Year"
Select dates Aug. 16 - May 14

Source: Public Chicago

The most pleasant time of year in the city, at a one of the most fashionable places
Most dates October-November

Source: Virgin America

Snag discounted fares on Conde Nast Traveler's 'Best U.S. Airline.'
Oct. 31 - Feb. 28

Source: Chicago Symphony Orchestra

Chicago Symphony Orchestra's opening the 125th season with buy one, get one free tickets for the Symphony Ball and 25% off five fall concerts
Oct. 16, 20

Source: Briar Street Theatre

"Blue Man Group" is a unique theatrical production that features Grammy-nominated live music, comedy and multimedia theatrics
Shows through Dec. 24

Source: Avis

This exclusive deal is combinable with additional perks like free upgrades, free weekend days or discounts on weekly rentals
Through 2015

Source: The House Theatre of Chicago

Save up to 40% on holiday favorite "The Nutcracker," acclaimed magic show "The Magic Parlour" and world premiere "The Revel"
Shows through December


Latest Sales & Specials*

Next Two Weekends
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American Express Travel
October departures; more dates available
October departures; more dates available

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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