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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.

Planet Hollywood Costa Rica Resort
  • Additional 20% Off
  • $500 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Winter/Spring 2025 Deals

3 Nights From:

$1069*: 1/4-2/28

5 Nights From:

$1649*: 3/1-4/30

Summer 2025 Deals

5 Nights From:

$1499*: 5/1-6/30

Riu Palace Costa Rica
  • Up to 52% Off

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Winter/Spring 2025 Deals

3 Nights From:

$1189*: 1/4-2/28

5 Nights From:

$1699*: 3/1-4/30

Summer 2025 Deals

5 Nights From:

$1599*: 5/1-6/30

Secrets Papagayo Costa Rica
  • Up to 58% Off
  • $200 in Resort Coupons††
  • Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Winter/Spring 2025 Deals

3 Nights From:

$1199*: 4/1-5/31

Summer 2025 Deals

5 Nights From:

$1949*: 6/1-7/31

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. *$1069 price is based on travel from Chicago [ORD] to Planet Hollywood Costa Rica for 3 nights on February 18. 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 12/20/24. 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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