Go Now: Unbeatable End-of-Summer Travel Deals

Chicago’s tourists start to dissipate in September as warm weather lingers. It’s prime season for travel deals, and it's not too late to catch favorite downtown Chicago summer pastimes including Cubs baseball games, beach volleyball, and epic outdoor summer concerts. The average cheapest September airfare to Chicago from the 20 largest U.S. cities is only $93. And vacation rental rates that were $344 per night earlier in summer are only $228 in September, according to HomeAway.com.

If you’re here during Labor Day weekend, hit downtown’s Oak Street Beach for the AVP Pro Beach Volleyball Tour championships. From September 9 to 25, the World Music Festival takes over Millennium Park and the Chicago Cultural Center with free shows. And with any luck, by September, the new, taller Ferris wheel at Navy Pier will have shorter lines.

September is still high season for Vancouver, but flights remain reasonably priced. Average airfare deals from major U.S. markets to this Canadian city are only $332. Hotel deals are scarce but vacation rentals are an affordable alternative. According to HomeAway, Vancouver’s summer vacation rental rates drop 43 percent in September, to $1,085 per week or $155 per night.

In early September, the weather is dry and still warm enough for water activities like kayaking in Deep Cove or paddle boarding in False Creek. The city’s popular Granville Island is the hub for quirky, fun theatre performances during the Vancouver International Fringe Festival in September. And the Vancouver International Film Festival runs September 24 to October 9. With the U.S. dollar strong against the Canadian loonie, the end of summer is an excellent time to visit.

With daily high temperatures in the low 80s, Los Angeles’ weather is glorious in September. The June Gloom fog that often hangs around through July has finally lifted and the long-awaited sun shines brilliantly. The best flight deals from major U.S. cities hover around $162. Extend summer in the SoCal warmth and pay only around $259 per night with current Hotels.com deals at La Montrose Suite Hotel, a stylish West Hollywood hotel two blocks from the Sunset Strip.

Foodies will find deals at the new Smorgasburg, a weekly open-air market with more than 50 local food vendors at the Alameda Produce Market site. Inspired by the popular Brooklyn flea market concept with the same name, Smorgasburg showcases bites from the city’s most popular restaurants and imaginative chefs.

It’s crazy cheap to fly to Costa Rica in September. Flights from Ft. Lauderdale are only $136, an unbeatable deal—especially if you’re close enough to drive to Ft. Lauderdale or can get there using your air miles. In San Jose, expect to pay less than $100 per night for lodging whether you stay in a vacation rental or book a hotel room.

Early September on the Osa Peninsula south of San Jose sees the return of migrating whales and is the time of the Whale and Dolphin Festival. If you visit on September 15, you can experience the country’s Independence Day holiday with parades, performances, and thousands of students carrying the Independence Torch from city to city. At exactly 6 p.m., the entire nation pauses to sing the national anthem.

Sin City sizzles above 100 degrees in June, July, and August. But by mid-to late September the temperatures relent, dropping to the low 90s and upper 80s. There are plenty of flight deals from major cities across the country, with fares to Vegas averaging $151. Hotels.com lists deals at a 30 percent savings for September dates. A recent search turned up rates starting at $238 per night at Treasure Island Hotel & Casino. This summer, the hotel opened a new interactive Marvel comics experience called Avengers S.T.A.T.I.O.N. that allows guests to see original movie props and virtually engage with the Hulk, Captain America, and other Avengers icons.

Between September 23 and 25, the annual Life is Beautiful festival hits the streets of downtown, with Mumford & Sons headlining this year. And country music fans can see Luke Bryan and Toby Keith at the Route 91 Harvest Country Music Festival during the last weekend of September.

Now is the time to explore an Eastern European capital city without breaking the bank. Fly in September from New York or D.C. to Sofia with deals averaging $494. A recent Hotels.com search uncovered September savings of 15 to 39 percent for a range of accommodations, from the Central Park Hotel ($101 per night) to the five-star Alexander Business Apartments ($224 per night).

With comfortable weather for touring—sunny skies and temperatures in the 70s—you’ll enjoy wandering Sofia’s impressive monasteries, domed cathedrals, Ottoman mosques, and UNESCO heritage sites. And the waterfalls and hiking trails of Mt. Vitosha, located just a short bus ride from the city, are also beautiful this time of year.

There are advantages of being home to the world’s busiest airport. Among them: terrific deals to get here. You can fly into Atlanta from eight U.S. cities for $79 or less in September. End-of-summer lodging is affordable, too. On a recent Hotels.com search, the Ellis Hotel at Peachtree came up at $162 per night, a 39 percent savings. HomeAway’s Atlanta vacation rentals are 21 percent cheaper in September than they are the rest of summer.

Plan a visit for one last summer hurrah here on the country’s first virtual reality roller coaster. Six Flags Over Georgia’s New Revolution at Dare Devil Dive, which opened last spring, sends you off on a real rollercoaster after you strap on a virtual reality headset that makes you a co-pilot in a fighter jet during an alien invasion. For a low-key alternative, head to the Atlanta BeltLine Lantern Parade on September 10. Hundreds of locals converge on the BeltLine walkway with glowing lanterns to create a magical nighttime processional.

Snag one of the $541 Hong Kong flight deals this September from Houston, Los Angeles or San Francisco to see one of China’s most important events of the year: the Mid-Autumn Festival. Since the Tang Dynasty, the festival has celebrated the fall harvest. Get in on the fire dragon dances, illuminated lantern displays, stage shows, carnivals, and homemade mooncake pastries offered in gratitude to the heavens.

American Airlines launches a new nonstop flight from Los Angeles to Hong Kong starting on September 7. Weekly vacation rental rates with HomeAway average $1,070 in September, a 29 percent drop compared to early summer. And only in September you can revel in the luxury and exclusivity of the Landmark Mandarin Oriental hotel without the expense of booking a room—from September 1 to October 31, the hotel will open the pop-up Bar High Five HK, a micro version of the glamorous Bar High Five, one of Asia’s top-rated bars.

Gorgeous autumn color arrives early in Denver, just in time for travelers to catch end-of-summer deals. In September, score flight deals averaging $139 from major U.S. cities to Denver, then head for the mountains to see Colorado’s iconic aspens transform to a glowing sea of gold against blue skies. Mid-September also marks the beginning of mating season for elk in Rocky Mountain National Park, 80 miles from Denver, where male elks bugle and spar until mid-October.

Football fans can see the Broncos defend their Super Bowl title and book the $135 per night Mile High Sports Fan Package at the Hyatt Regency Denver at Colorado Convention Center near the stadium. You’ll also find savings on vacation rentals in Denver. On average, HomeAway’s rates are $198 per night in September—$52 lower than typical May-through-August rates.

Summertime is the rainy, low season for Puerto Vallarta, but undeterred adventurers will find warm temperatures, outdoor fun, and great values. Flight deals average $387 from 20 U.S. cities in September. Four-star hotels on the beach, including Westin Resort & Spa and CasaMagna Marriott Resort & Spa, start at $119 per night. These resorts are part of Puerto Vallarta’s sea turtle conservation efforts. From July through mid-December, you can see how the turtle nests are protected and, once the babies are born, help release them into the ocean.

In the Sierra Madre Mountains surrounding the city, the dense jungle is an especially lush playground in September. Canopy tours send you flying from treetop to treetop on zip lines among colorful birds, orchids, vanilla vines, agave plants, and poinsettias.