Want to talk? Give us a Call



Chicago Last Minute Deals

Last Minute Deals From Chicago

Don't Miss Out: Limited Time Offers on Cheap Deals from Chicago

Head to the beach in a hurry with a low-priced travel package from Vacation Express! Find amazing last minute deals to fly from Chicago to your favorite destinations in Mexico and the Caribbean. With a last minute deal, you can easily book your flight from Chicago, hotel, local representative and all taxes for one discounted price. Book an all-inclusive hotel deal in Cancun, Riviera Maya, Punta Cana, Jamaica or any of our other destinations and enjoy your meals, unlimited drinks and exciting activities at no extra cost.

Find your next vacation by using our booking box to the left and selecting your ideal beach getaway and the dates you wish to travel.

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


All Ritmo Cancun Resort & Waterpark
Kids Stay, Play, & Eat Free

6-Night All-Inclusive Packages w/ Non-Stop Air
Travel: Apr 15, Apr 22, Apr 29, May 6 , May 13, May 20
+[$50-$510] Feb 18, Feb 25, Mar 4, Mar 11, Mar 18, Mar 25, Apr 1, Apr 8



Tukan Hotel & Beach Club
Conveniently Located in the Heart of Playa del Carmen

6-Night Inclusive Plan Packages w/ Non-Stop Air
Travel: Feb 18, Feb 25; Mar 4
+[$30-$360] Mar 11, Mar 18, Mar 25; Apr 1, Apr 8, Apr 15, Apr 22, Apr 29; May 6, May 13, May 20



Riu Naiboa
Amazing Rates

6-Night All-Inclusive Packages w/Non-Stop Air
Travel: May 7
+[$80-$480] Feb 26 Mar 5 Mar 12 Mar 19 Mar 26 Apr 2 Apr 9 Apr 16 Apr 23 Apr 30



Deja Resort
Excellent Hip Strip Location + 1st Child Stays and Eats Free

5-Night All-Inclusive Packages w/ Round-Trip Air
Travel: 11/1-12/15
+[$30] 1/3-1/31


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. *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 and description of all services, please refer to the Vacation Express 2017 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 at the above prices are from Chicago Midway International Airport or O'Hare International Airport, are limited and subject to change without prior notice and are on coach air with Spirit Airlines, US Airways, 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. Mandatory $10 Tourist Card must be purchased upon arrival to Punta Cana and is not included in above package prices. Book by 10/11/17. 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.