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$48.86·PayVibe Travel·3N/4D$49·Exploria Resorts·2N/3D·1BR condo sleeps 4$49·Westgate·2N/3D·3 days / 2 nights$49·Exploria Resorts·2N/3D·1BR condo sleeps 4$49·Exploria Resorts·2N/3D·1BR condo sleeps 4$49·BestVacationDealz·3N/4D·4 Days / 3 Nights$49·Cheap Vacation Getaways·2N/3D·Resort accommodation…$50·VacationVIP·2N/3D·3 Days / 2 Nights$50·PayVibe Travel·3N/4D$50·VacationVIP·3N/4D·4 Days / 3 Nights$51.19·PayVibe Travel·3N/4D$56.87·PayVibe Travel·3N/4D$57.42·PayVibe Travel·2N/3D$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·Resort close to Silv…$59·Discover Branson·3N/4D$59·Westgate·3N/4D·Oceanfront resort cl…$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·4 Premium Show Ticke…

$48.86·PayVibe Travel·3N/4D$49·Exploria Resorts·2N/3D·1BR condo sleeps 4$49·Westgate·2N/3D·3 days / 2 nights$49·Exploria Resorts·2N/3D·1BR condo sleeps 4$49·Exploria Resorts·2N/3D·1BR condo sleeps 4$49·BestVacationDealz·3N/4D·4 Days / 3 Nights$49·Cheap Vacation Getaways·2N/3D·Resort accommodation…$50·VacationVIP·2N/3D·3 Days / 2 Nights$50·PayVibe Travel·3N/4D$50·VacationVIP·3N/4D·4 Days / 3 Nights$51.19·PayVibe Travel·3N/4D$56.87·PayVibe Travel·3N/4D$57.42·PayVibe Travel·2N/3D$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·Resort close to Silv…$59·Discover Branson·3N/4D$59·Westgate·3N/4D·Oceanfront resort cl…$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·4 Premium Show Ticke…

Vacation Deals in Chicago, IL

Vacation deals in Chicago, IL.

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About Chicago Vacation Deals

Vacation deals in Chicago, IL. Browse and compare the best vacation deals available in Chicago. These resort deals include stays at deeply discounted rates — often 70-80% off retail. Deals typically include a Chicago resort stay with perks like free parking, resort credits, and loyalty points from top brands.