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The best destinations for celebrating summer’s biggest moments

Make the most out of Father's Day, the Fourth of July, and Labor Day weekend in destinations and hotels that enhance these fun summer celebrations.

By Hilton's team of expert travel writers | May 22, 2025 (Updated June 26, 2025)

Summer planning is well under way, and some of the best summertime celebrations are coming up fast. Discover the top destinations and hotels for amplifying your festivities on Father’s Day, the Fourth of July, and Labor Day weekend.

Father’s Day in Chicago

If the father figure in your life loves history, culture, and deep-dish pizza, then a getaway to Chicago is a must. Stay at Hilton Chicago to be in the heart of the Windy City and within walking distance of Soldier Field to catch a game or enjoy a concert. Overlooking Grant Park, the hotel is in the Pilsen neighborhood, which is known for its culturally rich arts community and vibrant dining scene. Spend a few hours with dad exploring the nearby Art Institute of Chicago before grabbing lunch at the hotel’s traditional Irish pub, Kitty o’Sheas, where you can savor farm-to-fork Irish fare. After touring the city or taking a leisurely walk along famed Michigan Avenue or a bike ride along the Chicago River waterfront, end the day with a classic deep-dish pizza; the city is bursting with amazing foodie options. Sweeten dad’s day even more by treating him to a brownie from Palmer House, a Hilton Hotel — the iconic hotel where it was invented — it’s guaranteed to earn you some serious brownie points.

Fourth of July in Boston

Considering Boston is where the Declaration of Independence was proclaimed in 1776, it’s no surprise that the city has some of the best Fourth of July celebrations in the country. Here, the party lasts four full days from July 1st to July 4th, during which the city’s famous Boston Harborfest delights visitors with live music, historical reenactments, guided Freedom Trail walks, boat tours, clam chowder samplings, and even a boat parade in the Inner Harbor. Best of all, Boston’s top Fourth of July festivities are all within walking distance of Canopy by Hilton Boston Downtown, making the property an ideal home base for all your holiday plans. Not in the mood to walk? Hop on one of the hotel’s complimentary Canopy Bikes to get around even faster.

Labor Day weekend in Charleston, South Carolina

From Southern hospitality and history to comfort food and pristine beaches, there’s never a bad time to visit Charleston. But what makes a Labor Day weekend visit so special is that you can also attend the Lowcountry Jazz Festival and enjoy performances by award-winning jazz singers and musicians. For travelers looking to combine a bit of history with a weekend of fabulous shopping, Hilton Club Liberty Place Charleston is conveniently found near the shops on King Street and the historical French Quarter. Take a thirty-minute stroll over to the colorful homes of Rainbow Row and the historical Battery promenade and fortified seawall. Here you’ll find more shops, restaurants and museums, including the International African American Museum.

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