Escape the Frigid Chicago Winter: Time to Book Your Vacation!

It’s a frigid Monday here in Chicago—sun shining but the cold truly biting. With the Bears’ season over, many of us are left craving something exciting to look forward to. What better way than planning a sunny getaway? At Windy City Travel, we’re seeing lots of travelers booking warm-weather flights this February from Chicago with convenient nonstop options.

Popular nonstop winter flights include:

  • Cancún, Mexico
  • San Juan, Puerto Rico
  • Fort Lauderdale, Tampa, Orlando, Miami – Florida favorites
  • Phoenix, Arizona
  • Las Vegas, Nevada
  • Jamaica

When flying this time of year, nonstop flights are key—weather delays can happen, so we aim to get you there smoothly.

Top Resort Deals to Warm Your Winter 

If you love Dreams and Secrets resorts, check out the newly refurbished Dreams Puerto Morelos. Formerly Secrets Silver Sands, this four-star family resort offers a fantastic package:
3 nights including flights, all meals, drinks, taxes, and tips
Price: $840 per person on select departure dates

Another fantastic option is the Ibero Star Waves Paraiso Del Mar, about 30 minutes from Cancun Airport. This fabulous hotel boasts a beautiful beach and is part of a massive Ibero Star complex with five resorts — starting at $890 per person.

Adults-only travelers will love the Rio Latino, a 4.5-star vibrant property priced at $882 for three nights.

And for an iconic getaway, consider the Atlantis Paradise Island in the Bahamas. Currently, there’s a remarkable 35% savings deal including daily breakfast for two — but hurry, this must be booked by January 26 for travel between March 1 and November 22. Whether you choose the Royal Atlantis, The Cove, The Reef, or The Coral, you’ll be immersed in luxury surrounded by amazing aquatic life — it’s like living inside an aquarium!

Why Choose Windy City Travel? Your Experts in Adventure and Value 

Don’t let the cold get you down. Contact us to plan a warm weather vacation.