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Chicago Early Booking Deals

Best Vacation Packages From Chicago

Round-Trip Flights and Resort Vacations

If you like to plan ahead with an early bird deal, look no further! With round-trip air for 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 to the left.

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.

CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  JAMAICA  ▪  LOS CABOS  ▪  COZUMEL  ▪  NASSAU  ▪  PUERTO VALLARTA  ▪  GRENADA  ▪  PANAMA

CANCUN

Golden Parnassus Resort & Spa
  • Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

6 Nights From:

$799*: 4/1-5/31

 

$949*: 6/1-7/31

RIVIERA MAYA

Secrets Capri Riviera Cancun
  • Adults-Only Getaway
  • $200 Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

6 Nights From:

$1259*: 6/1-7/31

 

$1057*: 8/1-9/30

PUNTA CANA

Royalton Punta Cana
  • $300 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

4 Nights From:

$694*: 4/1-5/31

6 Nights From:

$1333*: 6/1-7/31

 

$1134*: 8/1-9/30

JAMAICA

Sunscape Splash Montego Bay
  • $200 Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

6 Nights From:

$931*: 4/1-5/31

 

$1219*: 6/1-7/31

LOS CABOS

Riu Santa Fe
  • Kids Stay, Play & Eat Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

6 Nights From:

$924*: 4/1-5/31

 

$1099*: 6/1-7/31

COZUMEL

El Cozumeleno Beach Resort
  • Spring: Exclusive Deal at Family-Friendly Resort
  • Exclusive Sale
  • Summer: 20% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

6 Nights From:

$1028*: 4/1-5/31

 

$1099*: 6/1-7/31

NASSAU

The Royal at Atlantis
  • Lunch Included††
  • Up to $300 in Resort Credits††

EUROPEAN PLAN PACKAGES WITH ROUND-TRIP FLIGHTS

4 Nights From:

$1156*: 4/1-5/31

6 Nights From:

$1936*: 6/1-7/31

 

$1447*: 8/1-9/30

PUERTO VALLARTA

Crown Paradise Club
  • Kids 12 & Under Stay, Play & Eat Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

6 Nights From:

$947*: 4/1-5/31

 

$1029*: 6/1-7/31

GRENADA

Royalton Grenada Resort & Spa
  • Up to 78% Off
  • Up to $600 in Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

4 Nights From:

$1299*: 4/1-5/31

6 Nights From:

$1799*: 6/1-7/31

 

$1677*: 8/1-9/30

PANAMA

Riu Playa Blanca
  • 40% Off
  • Kids Stay, Play & Eat Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

4 Nights From:

$1295*: 4/1-5/31

6 Nights From:

$1329*: 6/1-7/31

 

$1358*: 8/1-9/30

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
Kid's 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 applies to hotel cost only. Airfare, transfers & booking fees not included. ††Restrictions apply. Call for details. *Prices reflect hotels that feature Breakfast Plans, Inclusive Plans, European 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. Only valid for new bookings. For full terms and conditions, hotel and description of all services, please refer to the Vacation Express 2020 Brochure or call for details. Vacation Express now accepts debit cards that offer the same consumer protection as credit cards. Some upgrades are subject to availability upon check-in. Packages are limited and subject to change without prior notice and are on coach 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. Book by 2/19/20. 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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