Prices quoted are examples, valid for travel during dates listed above. Rates may be higher for other days of the week. Surcharges apply to weekends, holidays, special events, and convention periods. Restrictions apply. Rates are subject to change until purchased. Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. See our Terms and Conditions for more information about our policies. Free Night offers must be reserved for consecutive nights to receive the free night. Offer valid for room and tax only. Additional fees may apply. Limited number of rooms available. Promotion Code not combinable with any other offer. Promotional code intended for redemption by individual consumer only. Valid on published scheduled SWA-operated service only. Packages must be booked on southwestvacations.com and at least one day before departure date before 6 pm Central Time.

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!

Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.
*Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
Just how cheap is it? If you get yourself to Isla Grande -- part of the Islas del Rosario just off the country’s north coast -- it’s a tropical paradise for as cheap as you care to make it. Although there are fancier resorts available, at eco-hotels such as La Cocotera, Las Palmeras, or El Hamaquero, you can sleep in a beachside hammock for just $10 a night. For $20, you’ll also get you three meals, including a freshly caught and grilled fish dinner. Or, pro tip: A local can bring you freshly caught lobsters on request from anywhere between $10 to $30 a day. Sneak into the upmarket Hotel Majagua and grab a piña colada for $5, or go to the inland village for cut-price cervezas. (If you want more privacy, lodging starts at around $30 per room, and goes up to between $90 to $250.)
Bali, Indonesia is a bucket-list must: beautiful beaches, ornate temples, delicious food and stunning vistas—this island is where travel dreams become reality! Combine cheap flights with a super affordable 4-star hotel, and say hello to a honeymoon or vacation that won't destroy your budget. What's Included? Based on two people sharing, this vacation deal includes…
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