Chicago Vacation Packages

Want to book a vacation to Chicago? Whether you are off for a romantic vacation, family trip, or an all-inclusive holiday, Chicago vacation packages on TripAdvisor make planning your trip simple and affordable.

Find the perfect vacation package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travelers like you have written 292,142 reviews and posted 50,084 candid photos for Chicago hotels. Book your Chicago vacation today!

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At TripAdvisor, we believe in the power of travel — and in helping you make the most of every trip. With over 500 million candid traveller reviews, we can help you make the right choice when you shop for hotels, restaurants, and attractions. You'll also find low airfares, free travel guides, worldwide vacation rental listings, popular forums with advice about virtually every destination, and more. When it’s time to book, we can help you save up to 30% on hotels, checking 200+ sites to find you today’s lowest prices. And when you’re on your trip, our free mobile app is your ultimate travel companion.