Cheap holidays to Chicago, IL

If you're on a mission to find cheap holidays to Chicago, IL, look no further. At WestJet Vacations, we offer our guests the best rates at the area's finest hotels and resorts, making it easier than ever to enjoy the greatest attractions in Chicago, IL, like Navy Pier, Winter WonderFest and the Million Dollar Quartet. Our top priority is to provide you with the package that best suits your budget and schedule. So don't put off your trip to The Windy City any longer: book with WestJet Vacations today.

Vacation finder

Looking for a the ultimate getaway? We can help you find it.

Your next memorable getaway begins here

WestJet Vacations is here to offer you the great cheap holidays to Chicago, IL you've been searching for. Not only do we have a fantastic selection of vacation packages — thousands, in fact — but we're also happy to offer you WestJet dollars® for every WestJet Vacations package you take as a member of our rewards program. In addition, you can benefit from an extensive and dependable flight schedule — and an exceptional guest experience from start to finish. At WestJet, we understand that plans can change, which is why you can feel good knowing you can change or cancel your package at no additional cost within 24 hours of booking.

WestJet wants to take you away on your next getaway. Book your perfect vacation now!


Search for great WestJet vacations


Find holidays in Chicago, IL: