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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.

JAMAICA  ▪  CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  COZUMEL

JAMAICA

Samsara Cliff Hotel
Located on the Beautiful Cliffs of Negril

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:
$796*: Now-6/30
6 Nights From:
$1185*: 7/1-8/31
$949*: 9/1-9/30
Sunscape Splash Montego Bay
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:
$949*: Now-6/30
6 Nights From:
$1377*: 7/1-8/31
$1079*: 9/1-9/30
Riu Palace Tropical Bay
Up to $600 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:
$1112*: Now-6/30
6 Nights From:
$1679*: 7/1-8/31
$1378*: 9/1-9/30
Couples Tower Isle
6th Night 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:
$1247*: Now-6/30
6 Nights From:
$1519*: 7/1-8/31
$1429*: 9/1-9/30

CANCUN

Reflect Krystal Grand Cancun
$200 Resort Coupons†† ▪ Kids Stay, Play & Eat Free [Select Dates]

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:
$655*: Now-6/30
6 Nights From:
$899*: 7/1-8/31
$1056*: 9/1-9/30
Riu Palace Costa Mujeres
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:
$769*: Now-6/30
6 Nights From:
$1099*: 7/1-8/31
$1159*: 9/1-9/30
Temptation Resort Cancun
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:
$822*: Now-6/30
6 Nights From:
$1179*: 7/1-8/31
$1213*: 9/1-9/30
Hyatt Ziva Cancun
Luxury Summer Deal Near the Best Shopping & Nightlife

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:
$1226*: Now-6/30
6 Nights From:
$1586*: 7/1-8/31
$1537*: 9/1-9/30

RIVIERA MAYA

Riu Lupita
Exclusive Deal

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-6/30
6 Nights From:
$799*: 7/1-8/31
$769*: 9/1-9/30
Iberostar Paraiso Beach
$500 Discount Credits††

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:
$638*: Now-6/30
6 Nights From:
$847*: 7/1-8/31
$819*: 9/1-9/30
Valentin Imperial Riviera Maya
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:
$869*: Now-6/30
6 Nights From:
$1127*: 7/1-8/31
$1069*: 9/1-9/30
Royalton Riviera Cancun
Up to $300 Resort Credit††

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:
$899*: Now-6/30
6 Nights From:
$1217*: 7/1-8/31
$1119*: 9/1-9/30

PUNTA CANA

Natura Park Beach Eco Resort & Spa
Up to 60% Off All-Inclusive Fun for All Ages

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:
$615*: Now-6/30
6 Nights From:
$866*: 7/1-8/31
$768*: 9/1-9/30
Riu Bambu
Up to $2190 Resort Discount Coupons†† ▪ Up to 2 Kids Stay, Play & 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:
$749*: Now-6/30
6 Nights From:
$1099*: 7/1-8/31
$993*: 9/1-9/30
Iberostar Dominicana
Up to $500 Resort Discount Credits†† ▪ 1st Child Stays, Plays & 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:
$783*: Now-6/30
6 Nights From:
$1149*: 7/1-8/31
$1045*: 9/1-9/30
Royalton Reveal
Mystery Deal–Royalton Branded Hotel Guaranteed††

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:
$929*: Now-6/30
6 Nights From:
$1329*: 7/1-8/31
$1184*: 9/1-9/30
The Reserve at Paradisus Palma Real
Kids Stay, Play & 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:
$1121*: Now-6/30
6 Nights From:
$1655*: 7/1-8/31
$1528*: 9/1-9/30

COZUMEL

El Cozumeleno Beach Resort
Amazing Rates

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE ROUND-TRIP FLIGHTS TO COZUMEL

Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$683*: Now-6/30
6 Nights From:
$678*: 7/1-8/31
$699*: 9/1-9/30
Melia Cozumel
Special Low Pricing

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE ROUND-TRIP FLIGHTS TO COZUMEL

Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$714*: Now-6/30
6 Nights From:
$737*: 7/1-8/31
$746*: 9/1-9/30
Secrets Aura Cozumel
Includes Up to $2500 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE ROUND-TRIP FLIGHTS TO COZUMEL

Deposits as low as $235 per person when you select our Reduced Deposit Plan [RDP].

4 Nights From:
$883*: Now-6/30
6 Nights From:
$1179*: 7/1-8/31
$1090*: 9/1-9/30

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 5/22/19. 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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