KAYAK to Group Chats Everywhere: Book the Trip

New summer campaign turns “we should go” into “we’re booked” with billboard-sized reminders and AI tools that help group trips finally take off, so travelers can see more and spend less together

NORWALK, Conn., July 21, 2026 /PRNewswire/ — This summer, KAYAK is on a mission to get group trips out of the chat and into the calendar. New KAYAK research reveals that 84% of travelers have had a group trip get stuck in the chat, with plans spending an average of one to three months in group chat limbo. The culprit? 90% of travelers say it comes down to one friend who just won’t commit.

To help those group trips finally take off, KAYAK is launching a series of BookBoards, billboard-sized reminders across New York, Chicago and Los Angeles that give that one friend a nudge they can’t ignore. The fleet of digital billboards will feature personalized callouts for nominated friends, popping up in Times Square, near their offices and neighborhoods that gently encourage them to commit while inspiring all travelers to make their group trips happen. Nominations are now open at kayak.com/bookboards.

Friends Who Travel Together, Save Together

The campaign comes as travelers look for smarter ways to stretch their vacation budgets. With domestic airfare up 23% year over year and hotel rates up 3%, group travel offers one of the easiest ways to make a trip more affordable. Splitting accommodations and experiences amongst a group means seeing more and likely spending significantly less. From upgrading to a larger hotel room to booking a standout vacation rental together, KAYAK helps groups compare those options side by side, making it easier to find the right trip at the right price.

“Group trips don’t fail because people don’t want to go, they fail because planning gets complicated,” said Carolina Montenegro, SVP of Global Brand Marketing at KAYAK. “BookBoards are a playful way to remind us that we’ve all been that friend at one point. Sometimes, all we need is a little push to get the trip over the finish line.”

Group Travel Takes Center Stage

At the center of the summer travel campaign is a 90-second hero film starring actress, comedian and content creator Grace Reiter and her real-life friend and American High co-star Julia Dicesare, who sends an increasingly unhinged series of BookBoards to Grace to get her to finally book their group trip.

To nominate your group chat for a BookBoard, visit kayak.com/bookboards from July 21 through August 4. Throughout August, KAYAK will select submissions to appear on digital billboards across New York, Chicago and Los Angeles.

Because this year, the group trip isn’t staying in the chat. It’s finally getting booked.

KAYAK Names Top Destinations for 2026 Group Trips

To jumpstart group travel planning, these are the KAYAK’s top destinations (based on popularity and affordability) for groups based on 5+ travelers.

For more inspiration, KAYAK is also introducing a new “Group Trip“ feature built within KAYAK Explore. Travelers can easily filter for the most popular and affordable group getaway destinations with average round-trip airfare and nightly hotel rates each under $500.

AI-Powered Planning for Group Trips

While BookBoards inspire groups to finally commit to a trip, KAYAK’s AI-powered planning tools can help turn trip ideas into bookable travel plans. With Ask AI on KAYAK, travelers can chat naturally about their group’s preferences, priorities and dealbreakers while real-time travel options appear alongside the conversation, making it easy to search and compare as plans take shape.

Below are a few of KAYAK’s best group travel prompts to try with Ask AI:

• Help us plan a trip that fits different budgets and vibes
• Which group trip destination gives us the most value for a long weekend in September?
• What is the best hotel in Miami for a big group?
• Compare destinations in the US for a group with different interests – some want to try good food, others want to relax by the water
• Find us a hotel in a city known for live music that sleeps six without blowing the budget

About KAYAK
KAYAK, part of Booking Holdings (NASDAQ: BKNG), is a leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package. Trusted by millions of travelers, the KAYAK app makes travel planning seamless on iOS and Android and we also support business travelers with our corporate travel solution.

Methodology 
Group chat survey: Based on a poll of 2,000 U.S. adults (ages 18-45) who have booked travel online in the past year.

Summer Travel prices: Based on flight and hotel searches between Mar. 1, 2026 and Jun. 29, 2026 for travel between May 21, 2026 and Sept. 8, 2026. They were compared to searches between Mar. 1, 2025 and Jun. 29, 2025 for travel between May 22, 2025 and Sept. 9, 2025. Changes in searches are approximate.

Group Travel destinations: 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.

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SOURCE KAYAK