Summer may have just wrapped up, but if you’re already dreaming about where you’d like to travel next year, it’s not too early to start planning. Getting an early start can give you more choices when it comes to flights, accommodations, cruises and resorts.
Here are some of the latest travel insights, deals and helpful tips from the team at Windy City Travel.
How far in advance can you book flights?
Airlines generally release their schedules about 330 days in advance, which means travelers can already begin looking at flights for much of summer 2027.
It may seem early, but if there’s a trip you’ve been dreaming about for next summer, now is a great time to start the conversation. Planning ahead can give you more options when it comes to flight schedules, seating and accommodations—especially during popular summer travel dates.
Are there any good international airfare deals right now?
We’re seeing some attractive roundtrip airfare options from Chicago to several international destinations.
Recent fares have included Reykjavik, Iceland starting around $399 roundtrip, Dublin around $541, Madrid around $554, Barcelona around $558, Rome around $563 and Paris around $610.
Airfares and availability can change quickly, but these are great examples of the opportunities you may find when you have some flexibility with your travel dates.
Is Iceland a good destination for a shorter getaway?
Absolutely! Iceland is closer to Chicago than many travelers realize. A nonstop flight to Reykjavik is approximately five and a half hours, making it possible to experience an international destination without spending an entire day getting there.
From dramatic waterfalls and geothermal hot springs to incredible landscapes and unique experiences, Iceland can even be a great option for a long weekend or shorter European getaway.
What are some of the least expensive months to travel?
January and February can often offer some attractive off-season rates, particularly for international travel.
Traveling outside the busiest seasons may mean lower airfare and hotel rates, along with fewer crowds. If your schedule is flexible, it’s worth exploring how changing your travel dates could impact the overall cost of your vacation.
Are there deals available for 2027 all-inclusive vacations?
Yes! We’re already seeing promotions that extend well into 2027.
Apple Vacations, for example, has featured offers on RIU Hotels & Resorts that include airfare credits and savings on select properties for travel through August 2027.
If an all-inclusive beach vacation is on your wish list for next summer, you don’t have to wait until 2027 to start planning.
What about cruise deals?
Cruise lines regularly release promotions that may include onboard credits, reduced fares, savings for additional guests and other incentives.
Recent promotions have included offers from Norwegian Cruise Line, Virgin Voyages and Carnival Cruise Line. Many cruise promotions have limited booking windows, so having a travel advisor watching the latest offers can help you take advantage of the right opportunity for your vacation.
What are a few simple travel tips before getting on a plane?
If you’re checking a suitcase, take a photo of your bag before handing it over to the airline. If your luggage is delayed or misplaced, you’ll have a picture showing exactly what it looks like.
When traveling to a new city, save a map showing the location of your hotel and make sure you have the hotel name and address readily available.
It’s also helpful to take a screenshot of your boarding pass and flight information so you can quickly access your flight and confirmation details without searching through emails or relying on an airline app.
Ready to Start Planning 2027?
Whether you’re dreaming about Europe, an all-inclusive beach getaway, a cruise or your next big adventure, now is a great time to start exploring the possibilities.
The travel advisors at Windy City Travel can help you compare options, navigate current offers and create a vacation designed around how you want to travel. Contact us to learn more.