Vacation rentals are becoming increasingly popular. Sites such as Airbnb, VRBO, and HomeAway permit homeowners to put their own properties up for rent whenever they won’t be using it. This is a good way to experience life as a local, because you’ll be staying in a residential area instead of one that caters to tourists. While some properties are tiny, cheap, and perfectly suitable for one person, vacation rentals are also a great way for a large group to get away together in a big house without having to pay for individual hotel rooms.
If you’re looking for a deep-dish pizza, world-class hockey, or a walk through Millennium Park, we can help you see—and eat—it all with a Chicago vacation package. There’s always something to do here in the crown jewel of Illinois, from a walk on Navy Pier to the gorgeous boutiques on the Magnificent Mile. Pardon our pun, but we’re sure “The Windy City” will “blow” you away!

Cook Islands - Exclusive $200 OFF per booking offer: Valid on new bookings made 9/24 - 12/2/18 for select travel 9/24/18 - 7/31/19, except for Little Polynesian Resort, which is valid for select travel 4/1 - 7/31/19. Discount is per booking, taken at time of booking and reflected in rates shown. Minimum 5-nights' accommodation at a participating hotel or resort and roundtrip transpacific airfare required. Offer not combinable with all specials and may be changed or withdrawn at any time.


Why you should go: Don’t let the name fool you; Isla Grande is an intimate, gorgeous Caribbean island just a 45-minute boat ride from Cartagena, full of exceedingly friendly locals and all the hallmarks of a tiny paradise. You’ve got your idyllic beaches, your lagoons of bioluminescent plankton that turn the water bright blue, your fresh seafood and multiple options for diving and canoeing. The chance to visit such a place is probably why you bother to earn money in the first place. - Daniel Cole, Thrillist contributor
Choosing the right vacation package has never been easier or more affordable. Check out some of our suggestions in the "Top Vacation Packages", "All Inclusive Deals" or "Last Minute Deals" sections. Whichever selection you choose, you can be sure that CheapOair will get you where you want to go at a price that can't be beat. We're constantly updating our great vacation deals and offers, so be sure to check back with CheapOair often. Now is the time to take advantage of our best deals while they last!
×