Vacation Packages from Chicago, IL

When it comes to driving vacations from Chicago, people love the classic American town charm of Galena, the peace and quiet of Harbor Country, and the gentle waters of Lake Geneva. All these destinations can be reached in a 3-hour drive or less. But to take a break from the famously chilly winter, cheap tropical vacations from Chicago are a no-brainer. The Bahamas, Jamaica, and Puerto Rico are all popular spots if you prefer a breather in the sun.

If you want to plan some of the cheapest vacations from Chicago, the period from February to April is great for nabbing flight and accommodation deals. The late winter and early spring months are prime winter break time. With the Christmas break over and the summer not yet on the horizon, explore fantastic deals on cheap beach vacations from Chicago in Florida, Cancun, and across the many breathtakingly beautiful islands of the Caribbean.

A nonstop flight from Chicago O'Hare International Airport to Daniel K. Inouye International Airport in Honolulu takes just over 9 hours. Bundle up your flights, accommodations, car rental, and activity bookings to make the most of fantastic savings on Hawaii vacations from Chicago. If you want to fly straight to Hawaii's Big Island, flights take an average of 12 hours and usually include a stopover.

There are several daily direct flights from Chicago to Dublin, Ireland. The fastest takes just over 7 hours, which means that if you fly out from Chicago in the evening, you can be tucking into a hearty plate of Irish Stew come lunchtime the next day. Washed down with a lovely pint of Guinness, of course. Effortlessly plan unforgettable Ireland vacations from Chicago with Expedia and save big by booking flight and accommodation packages.

Booking a Caribbeany vacation from Chicago has never been easier, thanks to Expedia's step-by-step guide to planning your vacation. Start by comparing your travel dates and destinations to find some of the best deals around. Being flexible with your travel dates is the key to finding top deals. Once you've found your package, simply add extras such as car rentals from trusted companies and tickets to popular attractions. Booking your vacation as a package with Expedia helps you compound your savings and plan a cheap Caribbean vacation from Chicago for the books.

It is not possible to fly direct from Chicago to Cuba. If you would like to plan beach vacations from Chicago with no stopovers, consider traveling to Nassau, the capital of the Bahamas. Explore a world of pristine white-sand beaches, crystal-clear waters teeming with coral reefs, and resorts all more luxurious than the last. Nassau can be reached in as little as 3h 30m from Chicago.

If you are an adventurous traveler, Cuba vacations from Chicago are worth it. Discover a country where time has stood still, and the pace of life is utterly relaxed. Visit tobacco plantations, experience the intoxicating rhythms of Cuban music, and dig your toes into the sand of some of the most beautiful beaches in the world. For a break from the harsh Chicago winter, other ideas include Costa Rica vacations from Chicago and Mexico vacations from Chicago.

When you book a vacation package with Expedia, you save money on both your hotel and your flights. Add in car rental and activities to save even more on your vacation budget. If you are planning a spontaneous trip, make sure to take a look at Expedia's fantastic selection of deals on last-minute vacations from Chicago. With last-minute deals, free flights or free extra nights of accommodation are often thrown in. It's a fantastic opportunity if you are planning last-minute beach vacations from Chicago or last-minute all-inclusive vacations from Chicago.

Choosing a package is one of the best ways to book cheap vacations from Chicago. When you bundle your flights and accommodation, you save money across the board. Expedia makes it easy for you to book your entire trip from start to finish, with a wide range of car rental options and exciting activities. And with Expedia's handy payment plans, you can book your vacation now and pay for it later. Make the most of hot package deals while they last.

It's easy to cancel your vacations from Chicago. Log into Expedia and head to “Trips”. There you can cancel, amend, or add extras to your reservations. You may need to pay cancellation fees. Please read your cancellation policy carefully before finalizing your booking.