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Chicago Vacation Packages

When you want to book the very best Chicago getaway, but you aren’t looking to empty your bank account on planning your trip, cheap vacation packages are the way to go. You can jump into an incredible vacay to Chicago for as low as $360 and keep your cash for the necessities—like the dreamiest fun times in town.

Looking to save some extra cash on your Chicago vacation? Try going on your getaway in , which is the off-season, and avoid the most popular time to vacation in the month of . Want to get away now-ish and still save? Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier.

If scoring the very best deal on your Chicago vacation is at the top of your to-do list, book your package with Hotwire and prepare to get way more bang for your buck.

Reserving a Chicago vacation package on a Tuesday is the cheapest day to book, or you can save more any day on Hotwire, with packages as low as $360.

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chicago right now?” When it’s time to book your vacation package, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

When you book a package deal on Hotwire, you can expect a Chicago vacation package with airfare and hotel. Want a rental car too? No biggie‚ you can add it to your package. Everything you need for an amazing trip? Check.