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Chicago Early Booking Deals

Best Vacation Packages From Chicago

Round-Trip Flights and Resort Vacations

If you're looking to travel last minute or like to plan ahead with an early bird deal, look no further! With round-trip flights this winter and spring from Chicago and all-inclusive resorts, you'll find the perfect package to Cancun, Riviera Maya, Punta Cana or Jamaica. 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

CANCUN

Occidental Costa Cancun
Up to $500 Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$649*: Now-2/28

6 Nights From:
$899*: 3/1-4/30
$879*: 5/1-6/30

The Pyramid at Grand Oasis
Early Booking Special

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$699*: Now-2/28

6 Nights From:
$1099*: 3/1-4/30
$1149*: 5/1-6/30

Krystal Grand Punta Cancun
Up to $200 Resort Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$785*: Now-2/28

6 Nights From:
$1163*: 3/1-4/30
$1199*: 5/1-6/30

Iberostar Cancun Star Prestige
Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$957*: Now-2/28

6 Nights From:
$1371*: 3/1-4/30
$1236*: 5/1-6/30

RIVIERA MAYA

Riu Lupita
Up to 35% Off Family-Friendly Resort in Playacar

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$599*: Now-2/28

6 Nights From:
$799*: 3/1-4/30
$699*: 5/1-6/30

Grand Riviera Princess
  • ▪ All-Inclusive, Beachfront Resort
    ▪ Free Upgrade†† to Deluxe Junior Suite w/Free Wi-Fi
  • ▪ 9 Restaurants, 13 Bars + 24 Hour Sports Bar
    ▪ 12 Pools & Kid's Club w/Pool + Luxurious Spa

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$529*: Apr 29, 30
$544*: Select Dates, Apr 1 - Jun 30
$589*: Select Dates, Jan 12 - Feb 28
$659*: Select Dates, Mar 1 - 31

Platinum Yucatan Princess All Suites Resort & Spa
  • ▪ Luxe, Adults-Only, All-Inclusive Resort
    ▪ Reservation Free Dining & Free Wi-Fi
  • ▪ Enjoy access to Grand Riviera Princess
    ▪ Deluxe Junior Suite w/24-Hour Room Service

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$669*: Apr 1 - Jun 30
Add $179*: Jan 12 - Mar 31

Ocean Coral & Turquesa
Up to 45% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$616*: Now-2/28

6 Nights From:
$859*: 3/1-4/30
$772*: 5/1-6/30

Hard Rock Hotel Riviera Maya
Up to 55% Off + Limitless All Inclusive

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$936*: Now-2/28

6 Nights From:
$1534*: 3/1-4/30
$1355*: 5/1-6/30

PUNTA CANA

Riu Naiboa
Up to $1335 Resort Discount Coupons††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$849*: Now-2/28

6 Nights From:
$1059*: 3/1-4/30
$899*: 5/1-6/30

Blue Beach Punta Cana
30% Off Luxury for Less Sale

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$891*: Now-2/28

6 Nights From:
$1199*: 3/1-4/30
$1099*: 5/1-6/30

Barcelo Bavaro Palace
$1000 Resort Discounts††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$944*: Now-2/28

6 Nights From:
$1289*: 3/1-4/30
$1198*: 5/1-6/30

Excellence El Carmen
Adults-Only Getaway ▪ Up to 57% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$1449*: Now-2/28

6 Nights From:
$1834*: 3/1-4/30
$1667*: 5/1-6/30

JAMAICA

Deja Resort
One Child 12 & Under Free ▪ Great, Hip Strip Location

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$849*: Now-2/28

6 Nights From:
$999*: 3/1-4/30
$919*: 5/1-6/30

Holiday Inn Montego Bay
  • ▪ Up to 65% Off, Free Upgrade** + Kids Stay & Eat Free
    ▪ Superior Partial Oceanview Room w/Free Wi-Fi
  • ▪ 2 Pools, Swim-Up Bar & Oceanfront Jacuzzi
    ▪ Beautiful White Sand Beach & Private Island

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

3 Nights From:
$699*: Feb 11 - 13, 23 - 27
$719*: Select Dates, Mar 1 - Apr 30
$739*: Select Dates, Jan 2 - Feb 28; May 1 - Jun 30

Royalton Negril
  • ▪ Up to 68% Off + $300 in Resort Credits††
    ▪ 24 Hr. Room Service + Reservation free dining
  • ▪ New Modern Luxury Beachfront Resort for All Ages
    ▪ Luxury Jr. Suite w/Balcony, Mini Bar + Free Wi-Fi

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

3 Nights From:
$889*: Apr 1 - Jun 30
Add $94*: Jan 2 - Mar 31

Legends Beach Hotel
Save All Season Long ▪ Book Now & Save

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$875*: Now-2/28

6 Nights From:
$1068*: 3/1-4/30
$868*: 5/1-6/30

Jewel Runaway Bay Beach & Golf Resort
Kids Up to 14 Stay, Play and Eat Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$1029*: Now-2/28

6 Nights From:
$1475*: 3/1-4/30
$1326*: 5/1-6/30

Royalton Blue Waters
$300 Resort Credit†† ▪ Up to 60% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS
Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$1318*: Now-2/28

6 Nights From:
$1776*: 3/1-4/30
$1493*: 5/1-6/30

Trending Beaches

Explore Our Most Popular Destinations from Chicago

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 *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 2019 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 carrier. 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 1/23/19. 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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