Travel Deals

Featured Travel Deals

Windy City Travel periodically offers travel deals in partnership with our travel providers. Please check out some of our featured offers at the links below. Feel free to contact us with any questions.

Virgin Voyages

Virgin Voyages’ award-winning dining, entertainment, cabins, and service offer elevated experiences for enhanced personal connections, while escapes to the sun-drenched shores of the Caribbean, or weeklong summer Mediterranean getaways from Barcelona and Athens will deepen your connection with the world.

Fall in love with every moment on board a new journey of extraordinary experiences with 65% off your 2nd Sailor and up to $500 in free drinks.*


Family Fun

A family trip is not only about breaking up the routine, it’s also about creating new bonds and strengthening relationships.

We’ll make sure to handle the planning so you can focus on having fun!

National Geographic Expeditions

For a limited time, save on 2025 National Geographic Expeditions Signature Land and River Cruise departures the world over.

Book by April 12, 2024 and enjoy the following offers:

  • Save $500 per person* on select 2025 Signature Land departures
  • Save $750 per person* on all available 2025 River Cruise departures



For some, it’s seeing the authentic beauty of the world. For others, it’s indulging in unparalleled luxury on board. There are thousands of reasons for sailing with Silversea, but from now until the end of February we think you’ll like:

$4,000 savings on Door-to-Door All-Inclusive fares – OR – $2,000 per guest, with a 15% refundable reduced deposit.*

Avalon Waterways

Innovative, transformative, original. Avalon Waterways has redefined cruising by going against the current and away from the ordinary. Delivering unparalleled experiences and boundless exploration, Avalon puts you in the captain’s seat to navigate your journey, fuel your passions and steer clear of the unexpected as you cruise down the world’s most memorable and mesmerizing waterways. One step aboard Avalon's modern, luxurious Suite Ships with the grandest views in cruising and you’ll see how the tides they are a-changin’.

RECEIVE A FREE EXTRA NIGHT on select 2023 or 2024 Avalon Europe River Cruises*

Additional Travel Deals

Land Vacations


Hot Offers