Travel News

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Navigating Flight Cancellations: How Windy City Travel Saves Your Week

Today we are helping you tackle the challenge of flight cancellations. With Alaska and United recently canceling hundreds of flights, many of our travelers were understandably concerned. But fear not, we’ve reached out to everyone affected and are working hard to ensure a smooth resolution by the end of this week. We handle contacting the […]
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2024 Travel Trends: Navigating the New Norms in Global Exploration

As we set our sights on the upcoming year, the travel landscape continues to evolve, offering fresh and exciting trends for avid explorers. 2024 is shaping up to be a year of mindful travel, emphasizing experiences that resonate on a deeper level. Here’s a glimpse into the future of travel, showcasing what’s trending and how […]

What to Pack for a River Cruise

Happy Friday to all! This is our Friday Travel update from Windy City Travel! Families are more determined than ever to see the world together, as we are seeing multi-generational travel continue to be a leading trend in travel this year. Many river cruises are meeting the growing demand with new opportunities for multi-generational families. […]
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The Top Travel Destinations for 2024

Our President, Lynn Farrell was recently asked to give her top 6 must-visit spots for 2024. Get ready to pack your bags, dust off the sunglasses, and update your passport because we’ve got the insider scoop on 2024’s hottest travel destinations. Check out her picks here.
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Our travel advisor featured in the travel news

Our very own Dennis Mayer was featured recently talking about why Europe is so popular for travel right now. Dennis Mayer, travel advisor, Foremost Travel Group (Windy City Travel, Oswego Travel and Traveloni), who attended ALG Vacations’ Spain FAM this summer, told TMR this about Europe: “In the post-COVID travel time we are in, Europe […]
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How to Pack for a Long Trip With Only a Carry-on

Is a lengthy vacation in your future but you want to avoid overpacking? Opting for carry-on only is a great way to avoid paying for checked bags, waiting around at baggage carousels after the flight, or dealing with lost luggage. Here are some tips for traveling carry-on only: 1. Choose the right bag Size and […]
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Three Tips for Spring Break Travel

Do the dog days of winter have you yearning for longer days and sunnier skies? Here are three tips for planning the perfect spring break getaway: 1. Start now Spring break is a popular time for traveling for families, couples, and party-goers alike, which can also make it a more expensive time to travel. To […]
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From Windy City to River City – Your Guide to a Richmond, VA Getaway

Busy work schedules, extracurricular activities, family obligations – life is busy! If you’re anything like us, you start planning a getaway as soon as a coveted free weekend is spotted on the calendar. Recently dubbed “a hidden culinary gem” by Forbes magazine, Richmond, VA, is quickly becoming a hot spot for travelers while maintaining its […]

All-inclusive Resorts with Kids

From when their first child is born, parents have high hopes of giving their children every opportunity, including traveling to new places and introducing them to new cultures, food, and lifestyles. But good intentions rarely come without some pain and suffering for parents. Travel can be complicated – with many reservations to keep track of. […]
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FALLing In Love with New England

Picking apples on a crisp September day. Octobers bursting with ruby, gold, and amber. Cozy nights in front of a crackling fire, sipping hot cider. It’s what autumn dreams are made of! From mountain peaks to seaside ports, with many quaint towns, New England is one of the most beautiful places to spend your autumn […]