Smooth Sailing & Sun-Soaked Destinations

It’s time to shake off the winter blues with your weekly dose of warm-weather inspiration, brought to you by your friends at Windy City Travel. Whether you’re dreaming of sun-soaked beaches or river adventures, we’ve got the inside scoop to fuel your wanderlust.

Cruise News to Get Excited About

River and ocean cruises are booming like never before! The cruise industry just reported its best six-week start ever for bookings — and it’s easy to see why. New ocean cruises and river journeys are popping up everywhere, with exciting destinations like Coco Cay and Adventure Cay making waves in the Caribbean. Plus, booking with a small deposit — sometimes as little as $50 or $200 — means you can plan your getaway far in advance without stressing your budget. Think 2027 vacations already in the mix!

Flights & Airfare: More Choices, Better Deals

United Airlines has purchased two new gates from Spirit Airlines at O’Hare, stepping up the friendly rivalry between United and American Airlines. What does this mean for you? More flights and better airfare options! When airlines compete for dominance, travelers win. This is great news for Midwest flyers looking for convenient and affordable travel options.

Travel Tips You Need to Know

Real IDs are now required for travel. If you don’t have a Real ID, a valid passport will work just fine. Without either, you can still travel domestically with a regular driver’s license—but be prepared to pay an extra $45 TSA fee and arrive earlier for the extra screening.

Why Nonstop Flights Are Your Best Bet This Season

Winter weather delays are no joke, and if you’re thinking warm getaway, nonstop flights are your best option. Luckily, Chicago offers nonstop service to incredible sunshine destinations including Cancun, Mexico City, Aruba, Curaçao, Grand Cayman, Punta Cana, San Juan (Puerto Rico), Nassau (Bahamas), Jamaica, Turks and Caicos, St. Lucia, St. Thomas, and St. Martin. Enjoy the convenience of a straight shot to paradise!

Planning Ahead Pays Off

Believe it or not, the booking engines are already buzzing for spring break 2027. Advance planning with Windy City Travel means you get better deals, flexible low deposits, and the best choice of flights and hotels. Don’t wait until the last minute — start your travel plans with us now

Whether it’s a family trip to Europe or a Caribbean escape, Windy City Travel’s experts are here, working remotely and ready to help you craft the perfect vacation. Contact us for personalized service and unbeatable advice.