The recent holiday weekend was a whirlwind for travelers returning from Caribbean destinations. With unexpected airport closures in places like Venezuela and San Juan, Puerto Rico, many were left wondering how they’d get home. But this is why booking with Windy City Travel is your best decision. Our dedicated team worked around the clock — even on weekends — to reach out to clients, secure hotel accommodations, and ensure safe returns. Travel can throw curveballs, but with us by your side, you’re never alone.
New TSA and Airline Updates You Should Know
Starting February 1, 2026, a $45 TSA fee each way applies to travelers without a Real ID, potentially adding up to $90 round trip. We strongly recommend visiting your local DMV soon to get your Real ID and avoid unexpected fees. Plus, the future is touchless! Digital IDs and precheck systems will make airport security faster and easier.
January 27 marks a significant change for Southwest Airlines: assigned seating is now standard. Say goodbye to scrambling for seats — your spot will be reserved when you board.
Good news for frequent flyers: United, Alaska, and American Airlines will offer free inflight WiFi in 2026. Just join their loyalty programs to stay connected and productive while flying. We love this upgrade to keep you online at no extra cost!
Cruises Set to Shine in 2026
An estimated 21.7 million people are expected to set sail this year! Thanks to our membership in the Signature Travel Network, Windy City Travel has exclusive access to contracted group rates on cruise lines like Royal Caribbean, Holland America, Norwegian, Virgin Voyages (adults only), and Explora Journeys. These rates beat booking direct with cruise companies – so before you book on your own, give us a call. We’ll tailor options with the best deals for your perfect cruise adventure.
Let’s Get Your Trip Started!
Our team at Windy City Travel is working hard remotely to find the best travel opportunities for you. Whether it’s your first trip of the year or your next unforgettable journey, let us handle the details. Reach out to connect with travel experts passionate about making your adventures seamless and inspiring.