If you’re looking for a deep-dish pizza, world-class hockey, or a walk through Millennium Park, we can help you see—and eat—it all with a Chicago vacation package. There’s always something to do here in the crown jewel of Illinois, from a walk on Navy Pier to the gorgeous boutiques on the Magnificent Mile. Pardon our pun, but we’re sure “The Windy City” will “blow” you away!
Europe - The Best Offers: Valid on new bookings made 10/1 - 12/16/18 for select travel 11/1/18 - 3/31/19. Blackout dates may apply. Minimum 3-night stay at a participating hotel or resort is required. Offers vary by hotel and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. All offers subject to change or cancellation at any time without notice.
Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Cheaptickets.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.

Choosing the right vacation package has never been easier or more affordable. Check out some of our suggestions in the "Top Vacation Packages", "All Inclusive Deals" or "Last Minute Deals" sections. Whichever selection you choose, you can be sure that CheapOair will get you where you want to go at a price that can't be beat. We're constantly updating our great vacation deals and offers, so be sure to check back with CheapOair often. Now is the time to take advantage of our best deals while they last!

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