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Chicago Adventure Vacation Deals

Chicago to Costa Rica Deals

All-Inclusive Vacation Packages w/ Round-Trip Air

Chicago, book your next adventure with Vacation Express today! You can book a trip from Chicago to Costa Rica now for one incredible price that includes round-trip air, your transfer, accommodations, local representative and hotel taxes. Plus, select an all-inclusive resort and enjoy an unbeatable deal, which includes all meals and unlimited drinks at one low price.

Looking for more savings? Visit our Cyber Week Vacation Deals page to browse deals at over 100 hotels and resorts. Plus, find more ways to save when you visit our Coupon Codes page.

Riu Guanacaste Hotel
  • Kids Stay, Play & Eat Free in 2022
  • Up to 48% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$1124*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$1199*: 1/4-2/28

 

$1727*: 3/1-4/30

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

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$1399*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$1729*: 1/4-2/28

 

$2049*: 3/1-4/30

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$1765*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$2164*: 3/1-4/30

 

$2258*: 1/4-2/28

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. *$1124 price is based on travel from Chicago [ORD] to Riu Guanacaste Hotel for 3 nights on November 30. 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. Book by 12/2/22. 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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