From beach breaks to city escapes, planning a cheap vacation with friends can seem like a financial challenge. But in my experience, going away as a group gives you more bang for your buck if you know where to go.
Here are 10 of the best affordable group vacations, backed up by KAYAK flight data.
Affordable group vacations backed by KAYAK data.
Cost top of mind? The below flights are based on average return costs and hotel prices are per night for a double room for two. Read on to get expert tips on how to find the best deals.
| Destination | Flight price | Hotel price |
|---|---|---|
| Las Vegas, Nevada, United States | $340 | $188 |
| Nashville, Tennessee, United States | $334 | $254 |
| Miami, Florida, United States | $352 | $261 |
| Chicago, Illinois, United States | $306 | $321 |
| San Diego, California, United States | $333 | $305 |
| San Juan, Puerto Rico | $400 | $308 |
| New York, New York, United States | $332 | $394 |
| Seattle, Washington, United States | $407 | $324 |
| Vancouver, British Columbia, Canada | $479 | $460 |
| Nassau, New Providence, The Bahamas | $492 | $479 |
Based on flight and hotel searches between Jan. 1, 2026 and Jun. 11, 2026 for travel between May 1, 2026 and Dec. 31, 2026 for 5+ travelers. Flight prices are based on round-trip, economy tickets; hotel rates are based on standard, double occupancy rooms. Prices are on average and are subject to change.
Chicago, Illinois
- Best for: City strolling & architecture goggling
- Group stay: Freehand Chicago
The Windy City is one of America’s most walkable cities. The Chicago Riverwalk puts you in the thick of the action. Start as a group at Lake Street and stroll its mile-plus tapestry of cafés and restaurants, bars and wineries, museums and street art. At its end, the incredible 18-mile Lakefront Trail opens up, hugging Lake Michigan’s shoreline and serving up skyline views you can’t buy.
Nashville, Tennessee
- Best for: Live music & honky-tonk partying
- Group stay: The Antioch Inn
Music City moves to its own beat, and it’s easy to get swept along for the ride. Travel the Honky Tonk Highway for year-round live music. Hop on the free Music City Circuit bus to take in the Ryman Auditorium, Country Music Hall of Fame and Lower Broadway where you can refuel at Robert’s Western World. Order the Recession Special – a fried Bologna sandwich, chips, beer and a moon pie for just $6.
San Diego, California
- Best for: Beaches & surfing
- Group stay: Avalon Buyout by AnantStay
With 70+ miles of public beach to laze on and world class waves to surf on, San Diego is the go-to for group adventure with an aquatic theme. The year-round perfect weather certainly helps. My pick is atmospheric La Jolla Cove for its evening sunsets and beach party picnics.
Las Vegas, Nevada
- Best for: Nightlife & celebrating
- Group stay: Flamingo Las Vegas Hotel & Casino
The sheer spectacle and scale of the Strip is tailor made for groups with its cavernous casinos, incredible eateries and wild bars. To the north, neon-lit Fremont Street is easier on the budget with free nightly live shows, street performances and cheaper drinks. For an escape from the city’s madness, tour Red Rock Canyon’s scenic loop on the city outskirts.
Miami, Florida
- Best for: Culture & art
- Group stay: Cottages El Portal
Miami can be more affordable for group trips than people might think. Art and culture is everywhere, with regular free art tours and culture crawls across the city. In Little Havana, bar hop from free merengue lessons at Ball & Chain to cocktails at Bar Nancy. On the third Friday of every month, Calle Ocho comes to life with the Viernes Culturales, a block party not to be missed.
New York, New York
- Best for: Iconic sights & experiences
- Group stay: Moxy NYC Times Square
Few cities in the world can match the city that never sleeps. Hit the streets of Manhattan for neck-craning views and world-famous landmarks. Take the free Staten Island Ferry to get up close to Lady Liberty.
Time your visit with Broadway Week for two-for-one theater tickets or try the TKTS booth in Times Square (right by the Moxy Hotel) for half-price same-day tickets.
San Juan, Puerto Rico
- Best for: A little bit of everything
- Group stay: Fortaleza Suites Old San Juan
Make it one to remember with a big trip to Puerto Rico – no passport needed for US citizens. The capital, San Juan, offers a bit of everything and caters to every taste, from the fine sands and glitzy towers of Condado Beach to the colorful and cultured Old Town.
Vancouver, British Columbia, Canada
- Best for: Hiking & nature
- Group stay: Luxury Home near Lonsdale Quay
Stanley Park is a rainforest within Vancouver’s city limits and epic for hiking. Rent bikes (tandems available!) and cycle the Stanley Park Seawall for rugged beaches and enormous views. Ride the Grouse Mountain Skyride aerial tram, big enough to carry groups to the city’s peak. Round out your stay with an organized craft brewery crawl through the many tasting rooms of Mount Pleasant.
Seattle, Washington
- Best for: Exploring by bike
- Group stay: Green Tortoise Hostel
Seattle loves cyclists. Use the budget-priced bike share program and hit the Urban Trail System to see the Emerald City’s neighborhoods, parks and waterfront at their best. Stop off at Pike’s Place Market for fish throwing, live music and a caffeine hit at the original Starbucks. Next door on Post Alley, add to America’s most disgusting artwork at the Gum Wall.
Nassau, The Bahamas
- Best for: Doing as little as possible
- Group stay: Breezes Bahamas
Nassau delivers the Caribbean at a pocket-friendly price. By day, glorious beaches, swimming with pigs and snorkeling the cavernous Thunderball Grotto. By night, Nassau and the fish fry at Arawak Cay complete with open-air live music, conch fritters and rum punches.
Expert tips to get the best group flight and accommodation deals.
KAYAK research shows that 68% of travelers are still planning to travel despite rising costs. Here’s how to make sure you’re getting the best deal for everyone.
- Set a Price Alert. Takes the hassle and guesswork out of when to book your flight and accommodation. KAYAK’s Price Alerts monitor flight and hotel prices daily and alert you as they go up or down, so you don’t miss a deal.
- Simplify with Ask AI. Skip the filters and plan your trip with KAYAK’s Ask AI tool. Ask conversational questions (“rental home in the Bahamas for eight people under $1,000 a night”) and get real-time results. Find direct flights and accommodation for everyone, plan detailed itineraries and share it all in the group chat. KAYAK data notes that 84% of travelers have had a group trip that’s never made it out of the group chat. Ask AI will change that.
- Check the best time to travel. KAYAK’s Best Time to Travel tool uses your origin, destination and length of stay to tell you not only the best time to travel but also the best time to book your trip. When it comes to group bookings, this can save serious dollars.
- Be flexible on travel dates. A little flexibility can go a long way toward easing the budget. Even just a day or two either side of your preferred travel dates can bring prices down. Traveling off season and mid week will also help. According to KAYAK data, January and November are the cheapest months for hotels, with Sunday check-ins tending to offer the best rates.
- Be ready to move fast when you find a deal. I know from experience how hard it is wrangling a group to act quickly, book and pay for a deal when it pops up. Once you’ve agreed on a budget, gather everyone’s travel details and payments into one place. Then when that Price Alert with the right deal goes off, you’ll be ready to pounce.
