Gave Saglie, Senior Editor at Travelzoo has some great deals for near and far. Find them all at travelzoo.com/tv/Chicago.
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Destination Matters
- Consider destinations you may have been priced out of in summer
- Look at spots that lower prices ahead of winter spikes
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Days Matter
- As business travel picks up after summer, consider flying on non-business-friendly days (Tuesday, Wednesday and Saturday)
- In business-friendly cities, weekends can be cheaper
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Check the Forecast
- Many shoulder season savings are driven by weather
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Check the Schedule
- Many attractions alter hours (or may close altogether) once busy summer season ends
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Consider the crowds
- Some destinations see leisure travel slow down but open their doors to conventions, field trips, etc., so plan accordingly
Deals as seen on TV
The Langham Chicago
Chicago
Much anticipated 5-Star deluxe hotel, which opens its doors in September
Property occupies the first 13 floors of the IBM skyscraper, which was declared a Chicago landmark in 2008 and
entered into the National Register of Historic Places
Hotel offers sweeping river and cityscape views, an upscale urban spa (w/ 67-foot indoor swimming pool) and 2
upscale dining options (inc. Travelle and Pavilion, which will serve Langham's famed afternoon tea)
$299/nt. (reg. $600)
Deal inc. $100 resort credit
Travel daily through Dec. 30 (inc. Labor Day, Thanksgiving and Christmas)
The City by Water
Kayak Chicago
Seasonal sale on four unique 3-hour tours by kayak
Four options include: the Architecture Tour, the Sunset Paddle, the Night Paddle (all on the River) and the Lake
Paddle (departing from North Avenue Beach)
All equipment is included, no experience is required, and plenty of parking is available near both launch sites
$63 for 2 (reg. $130)
Experience through Sep. 29
Christopher Place Smoke Mountains Resort
Newport, TN (7-8 hours from Chicago)
Elegant and romantic AAA 4-Diamond bed-&-breakfast overlooking the Great Smoky Mountain National Park
Secluded property stretches across 200 green acres and has only 9 rooms
Guest experiences include arts & crafts shopping, wine tasting, horseback riding, fishing, kayaking and taking on
more than 700 miles of Smokies hiking and rock climbing trails
$319 for a 2-night stay (50% off)
Deal inc. gourmet breakfast for 2 daily and waived resort fee
Travel through Sep. and in November; October stays require a 3-nt minimum stay
The Deals: Further Away
South of the Border Escape (For the Grown Ups)
Riviera Mata, Mexico
Roundtrip airfare from O'Hare to Cancun
7 nights at the Grand Palladium Colonial Resort & Spa
Deluxe resort offers 7 restaurants, 13 bars (inc. a swim-up bar) and 4 pools
Property is set along the Caribbean Sea on a long white sand beach and features lush gardens and lagoons
All-inclusive: all meals, cocktails/drinks, activities and tipping included
$879/pp ($500 off)
Deal inc. free upgrade to Junior Suite and airport transfers
Travel Sep.-Oct.
Tropical Escape (For the Kids)
Montego Bay, Jamaica
Roundtrip airfare from Chicago to Montego Bay
6 nights at the Holiday Inn SunSpree Resort Montego Bay
Resort features a kids club and a full-service spa, and each guest room has a private balcony or patio
Included activities include snorkeling, kayaking, miniature golf and tennis, and spa discounts are included
All-inclusive: all meals, cocktails/drinks, activities and tipping included
Kids stay & eat FREE
$839/pp ($400 off)
Travel Aug. 25-Dec. 19
European Vacation
Italy
Roundtrip airfare from Chicago to Rome
7 nights on the grounds of the Castello di Montegufoni Estate
This historic property is a 12th-century castle nestled in the Italian countryside among vineyards and mushroom and olive groves
The nearest village from the castle is a 10-minute stroll down the road, and Florence and Siena are within a half-hour drive, meaning guests are close to world-class art and fresh, locally sourced foods
Car rental with unlimited mileage included
$1279/pp ($800 off)
Add 2 nights in a 4-Star villa outside Rome for +$150/pp
Travel in November (harvest season)
Aqua Kauai Beach Resort
Lihue, Kauai, HI
Lush, plantation-style property set on 25 acres along a secluded beach
Resort amenities include 4 pools, a 75-foot lava tube waterslide and two whirlpool spas located in a secluded grotto
Guests get complimentary shuttle service to and from Lihue airport, as well as area golf courses, and there's a
complimentary mai tai reception every Tuesday
$600 for a 5-night stay for a family of 4 (reg. $1000)
Deal inc. upgrade to Ocean View Lanai Room and $25 activity credit
Travel through Dec. 20, inc. weekends; 3-nt. pricing $375 (reg. $600)
Tip: r/t airfare from Chicago to Kauai from $725 through Dec.
Trump International Hotel Las Vegas
Las Vegas
Super luxurious 5-Star resort in the heart of the Vegas Strip
All suites feature floor-to-ceiling windows, spa tubs and in-mirror plasma TVs
Resort is located near the Wynn, w/ easy access to shopping at Fashion Show Mall, which includes flagship
department stores like Neiman Marcus, Saks Fifth Avenue and Nordstrom
$79/nt. (45% off)
Deal features accommodations in a Suite
Travel Nov.-Dec.; price is $99 for Sep.-Oct.
Tip: r/t airfare from Chicago to Vegas from $256 through Dec.
