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Pleasant Holidays

Travel Type(s) Offered
Airfare and Hotel Packages
City Stays and Sightseeing
Hotel Only
Independent Travel
Budget Type(s) Served
Above Average
Top of the Line
Bookable Online?

With almost 50 years experience, Pleasant Holidays specializes in vacations to Hawaii, Mexico, Caribbean, Europe, Australia, New Zealand, Asia, South Pacific, Las Vegas and Costa Rica. Pleasant Holidays offers a wide variety of travel products from economy to luxury vacation packages at affordable prices, while delivering exceptional customer service. The Pleasant Holidays brands have sold over 9 million vacation packages since 1959.

Pleasant Holidays is one of the largest tour operators to Hawaii, Mexico, Costa Rica, Las Vegas, Caribbean, Europe, Asia and the South Pacific offering a comprehensive range of travel products. The company has long-term partnerships with some of the world's leading airlines, hotels, car rental companies, cruise lines, travel agencies and is the official travel provider to the NFL Pro Bowl annually in Hawaii. Pleasant Holidays has received numerous awards for excellence and has been awarded "Best Tour Operator - Hawaii" for 4 consecutive years by Travel Weekly Magazine.

Travel with the Experts! The Pleasant Holidays brands offer 50 years of experience to some of the world's most popular destinations.

Book a Pleasant Holidays trip online and SAVE!


Speak with an agent at our Oak Brook office at


Call 630-645-9500 to speak with a Travel Two Thousand agent about your Pleasant Holidays vacation.