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Chicago Early Booking Deals

Best Vacation Packages from Chicago

Vacation Packages w/ Round-Trip Air

If you like to plan ahead with an early bird deal, look no further! With round-trip air for summer, fall and winter from Chicago and all-inclusive resorts, you'll find the perfect package to the Caribbean, Mexico and Central America. Find our best deals below or pick your ideal dates and shop using our booking box on this page.

CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  JAMAICA  ▪  LOS CABOS  ▪  PUERTO VALLARTA  ▪  ARUBA  ▪  COSTA RICA  ▪  BAHAMAS

Riviera Maya

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$844*: 9/1-10/31

 

$1026*: 11/1-12/15

Punta Cana

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$919*: 11/1-12/15

 

$1019*: 9/1-10/31

Cancun

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$919*: 9/1-10/31

 

$1079*: 11/1-12/15

Jamaica

Grand Palladium Lady Hamilton Resort & Spa
  • Up to 65% Off
  • $600 Resort Credit for 5Nt+ Stays††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1098*: 9/1-10/31

 

$1296*: 11/1-12/15

Los Cabos

Krystal Grand Los Cabos
  • $200 in Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1089*: 9/1-10/31

Bahamas

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1399*: 9/1-10/31

 

$1523*: 11/1-12/15

Costa Rica

Riu Palace Costa Rica
  • $600 in Resort Discount Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1379*: 9/1-12/15

Puerto Vallarta

Hard Rock Hotel Vallarta
  • $100 Spa Credit per Room††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1599*: 9/1-10/31

 

$1667*: 11/1-12/15

Aruba

Riu Palace Antillas
  • Adults-Only Getaway
  • $590 in Resort Discount Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$2229*: 11/1-12/15

 

$2399*: 9/1-10/31

Trip Protection & Insurance

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
††Restrictions apply. Call for details. *$844 price is based on travel from Chicago [ORD] to Catalonia Yucatan Beach for 5 nights on October 15. 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 7/26/24. 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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