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!
A portion of all travel booked on American Airlines may be American Eagle® service. American Eagle service is operated by Compass Airlines, LLC, Envoy Air Inc., ExpressJet Airlines, Inc., Mesa Airlines, Inc., Republic Airline Inc., SkyWest Airlines, Inc., or Trans States Airlines, LLC. American Airlines, the Flight Symbol logo, American Eagle, AAdvantage and AAdvantage Million Miler are marks of American Airlines, Inc.

^Prices shown are per person based on double occupancy and include all airport, flight, and hotel taxes and fees except resort fees which are charged by the hotel upon arrival. Prices are valid for flight + hotel packages for the length of stay listed above to the featured destinations on the departure dates listed above. Pricing may differ when traveling from different origins, for longer than the length of stay shown, to different hotels not listed, or on dates not listed above.
Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Orbitz.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.
For prices that include airfare, all government-imposed taxes and fees, including the September 11th Security Fee, are included. Fares are for round-trip off-peak Main Cabin travel and are in U.S. dollars. For vacation packages that include domestic flights (within and between the U.S., Puerto Rico and the U.S. Virgin Islands), a checked baggage charge Opens in a new window of $25 each way for the first checked bag and $35 each way for the second checked bag may apply. For vacation packages that include international flights in Main Cabin for travel to or from the U.S. (including Puerto Rico and the U.S. Virgin Islands), a checked baggage charge Opens in a new window up to $100 may apply for the second checked bag. Exceptions may apply. Opens in a new window
Why you should go: Because nature and mild danger make you feel alive. Victoria Falls has a bungee jump, one of the world’s most high-octane whitewater runs, and the Devil’s Pool, a natural rock pool at the literal edge of the falls. Forget TLC’s admonitions: Inching your body out over the precipice and looking down into one of the seven natural wonders of the world is one of the most unforgettable things you’ll ever do. - Sarah Theeboom, Thrillist contributor
Why you should go: Because nature and mild danger make you feel alive. Victoria Falls has a bungee jump, one of the world’s most high-octane whitewater runs, and the Devil’s Pool, a natural rock pool at the literal edge of the falls. Forget TLC’s admonitions: Inching your body out over the precipice and looking down into one of the seven natural wonders of the world is one of the most unforgettable things you’ll ever do. - Sarah Theeboom, Thrillist contributor
Here's the deal—we've paired budget flights with a top-rated apartment rental in beautiful Aguadilla, Puerto Rico to create a Caribbean getaway for under $260 each! Your apartment is located just minutes from Crash Boat Beach, hiking trails, restaurants, and more. This is the perfect opportunity to escape winter without breaking the bank. What's Included? Based…
×