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Chicago Last Minute Deals

Last Minute Deals from Chicago

All-Inclusive Vacation Packages w/ Round-Trip Air

Enjoy a vacation on the beach with a last minute getaway from Vacation Express! Find amazing last minute deals from Chicago [ORD] to your favorite destinations in the Caribbean, Mexico and Central America. With a last minute deal, you can easily book your round-trip air from Chicago [ORD], accommodations, local representative and hotel taxes for one discounted price. Book an all-inclusive hotel deal and enjoy your meals, unlimited drinks and exciting activities at no extra cost or a European plan resort for your next getaway.

Looking for more savings? Visit our Cyber Week Vacation Deals page to browse deals at over 100 hotels and resorts. Plus, find more ways to save when you visit our Coupon Codes page.

CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  JAMAICA  ▪  LOS CABOS  ▪  PUERTO VALLARTA  ▪  SAINT LUCIA  ▪  COSTA RICA  ▪  NASSAU

Riviera Maya

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$493*: Now-10/31

Cancun

Crown Paradise Club
  • Kids Stay, Play & Eat Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$699*: Now-10/31

Punta Cana

Riu Naiboa
  • Up to $1516 in Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$989*: Now-12/15

Jamaica

Ocean Eden Bay
  • Up to 62% Off
  • Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$999*: Now-12/15

Nassau

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1039*: Now-12/15

Los Cabos

Riu Palace Cabo San Lucas
  • Up to $920 in Resort Coupons††
  • Enjoy Spectacular Views of Cabo Landmarks!

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1044*: Now-12/15

Costa Rica

Riu Guanacaste Hotel
  • Kids Stay, Play & Eat Free
  • Up to 48% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1124*: Now-12/15

Puerto Vallarta

Iberostar Selection Playa Mita
  • 45% Off Luxe, Beachfront Resort

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1296*: Now-12/15

Saint Lucia

Adults Only, Hideaway at Royalton Saint Lucia Resort
  • Adults-Only Getaway
  • Up to $600 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1779*: Now-12/15

Trip Protection & Insurance

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
Kid's hotel offer based on one child per full paying guest and offered on select departures only; qualifying ages and maximum number of kids vary by resort and does not apply to airfare, transfers & booking fees. ††Restrictions apply. Call for details. *$493 price is based on travel from Chicago [ORD] to BlueBay Grand Esmeralda for 3 nights on December 4. Advertised prices available for bookings made electronically through your travel agent or on vacationexpress.com; small service fee of $10 applies when booking through Vacation Express Call Center. Prices are per person, based on double occupancy. For full terms and conditions, hotel information and description of all services, please refer to vacationexpress.com or call for details. Some upgrades are subject to availability upon check-in. Packages above are from O'Hare International Airport, are limited and subject to change without prior notice and are based on travel on coach/economy air with Spirit Airlines, American Airlines or other U.S. certified carriers. Airfares are per person, reflect lowest available airfare at time of printing, are subject to change and are based upon availability of class of service. Baggage charges and allowances vary by carrier and can change frequently. Most major carriers are charging a fee for checked baggage. Some airlines, including Spirit Airlines, are charging a fee for all checked and carry-on baggage. Clients must check their respective airline for the most current baggage information. Some hotels in the Cancun, Riviera Maya, Isla Mujeres and Cozumel areas of Mexico charge an environment fee of approximately $1.21 per room, per night. Hotels in Saint Lucia charge a Country Sustainability Fee of $6 USD per person, per night Fees are subject to change without notice and are payable at the hotel. Book by 12/2/22. Not responsible for errors or omissions. Registered Florida Seller of Travel no. St 38441. State of California Seller of Travel Certificate of Registration #2107538-40.

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