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Chicago Last Minute Deals

Last Minute Deals from Chicago

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 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, accommodations, local representative and hotel taxes for one discounted price. Book a resort with a European plan or an all-inclusive hotel deal and enjoy your meals, unlimited drinks and exciting activities at no extra cost.

CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  JAMAICA  ▪  COZUMEL  ▪  LOS CABOS  ▪  PUERTO VALLARTA  ▪  TURKS & CAICOS  ▪  COSTA RICA  ▪  BAHAMAS

Cancun

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$584*: Now-10/31

5 Nights From:

$1428*: 11/1-12/15

Riviera Maya

Riu Palace Riviera Maya
  • Up to $850 in Resort Discount Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$688*: Now-10/31

5 Nights From:

$1525*: 11/1-12/15

Punta Cana

Royalton Bavaro Resort & Casino
  • Up to $600 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$724*: Now-10/31

5 Nights From:

$1265*: 11/1-12/15

Jamaica

Holiday Inn Montego Bay
  • Up to 58% Off
  • 1 Kid Stays, Plays & Eats Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$749*: Now-10/31

5 Nights From:

$1089*: 11/1-12/15

Los Cabos

Riu Palace Baja California
  • Up to $820 in Resort Discount Coupons††
  • Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$955*: Now-10/31

5 Nights From:

$1269*: 11/1-12/15

Cozumel

El Cozumeleno Beach Resort
  • Early Booking Bonus!

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$989*: Now-10/31

5 Nights From:

$1029*: 11/1-12/15

Costa Rica

Planet Hollywood Costa Rica Resort
  • $500 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1043*: Now-10/31

5 Nights From:

$1836*: 11/1-12/15

Puerto Vallarta

Grand Palladium Vallarta Resort & Spa
  • Up to 40% Off
  • $1500 Resort Credit on 4Nt+ Stays††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1199*: Now-10/31

5 Nights From:

$1629*: 11/1-12/15

Bahamas

Riu Palace Paradise Island
  • Up to $1260 in Resort Discount Coupons††
  • Adults-Only Getwaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1327*: Now-10/31

5 Nights From:

$1645*: 11/1-12/15

Turks & Caicos

BREAKFAST PLAN PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$1659*: Now-10/31

5 Nights From:

$2069*: 11/1-12/15

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. *$584 price is based on travel from Chicago [ORD] to Catalonia Grand Costa Mujeres for 3 nights on October 17. Prices reflect hotels that feature Breakfast Plans and All-Inclusive Plans. 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. Fees are subject to change without notice and are payable at the hotel. Book by 9/29/23. 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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