Search Deals on
Historic Route 66 Vacation Packages

Cheap Historic Route 66 Vacation Packages

You’re on the hunt for a steal of a deal on your Historic Route 66 vacation package. You’ve got your list of things you want, and you’re checking it twice: a ballin’ (on a budget) Historic Route 66 hotel, a champagne poppin’ flight (for a knock-off beer price), and maybe even a super-nice car rental (for a borrowed bike fee).

Think it’s all just a dream? Not when you book your Historic Route 66 vacation deal with Hotwire.

Are you for real with these vacation package deals

Daydreaming is even better when wildly good deals become your reality. Scoring hotel and flight deals to Historic Route 66 for a price that works with your budget is realer than real when you book your package with Hotwire. Ready to get all of your wildest dreams fulfilled (for way less than you expected)? Don’t sleep on these Hotwire deals.

Frequently Asked Questions About Vacation Packages

How much is a vacation to Historic Route 66?

When you want to book the very best Historic Route 66 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 Historic Route 66 for as low as $295 and keep your cash for the necessities—like the dreamiest fun times in town.

When is the best time to book a vacation package to Historic Route 66?

Looking to save some extra cash on your Historic Route 66 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.

How to get the best vacation package deals to Historic Route 66?

If scoring the very best deal on your Historic Route 66 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.

What is the cheapest day to book a vacation package?

Reserving a Historic Route 66 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 $295.

Can I vacation in Historic Route 66 right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Historic Route 66 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.

What does Hotwire Historic Route 66 travel package include?

When you book a package deal on Hotwire, you can expect a Historic Route 66 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.

Historic Route 66 Flight + Hotel Packages

Kimpton Gray Hotel, an IHG Hotel
Residence Inn Chicago Downtown/Loop
Waldorf Astoria Chicago
Hilton Garden Inn Chicago Central Loop
Fairmont Chicago at Millennium Park
Sophy Hyde Park
theWit Chicago - a DoubleTree by Hilton Hotel
Hilton Orrington / Evanston

Historic Route 66 Vacation Packages 3-4 Night Stays

The Langham, Chicago
Kimpton Gray Hotel, an IHG Hotel
Residence Inn Chicago Downtown/Loop
Sheraton Grand Chicago Riverwalk

Historic Route 66 Vacation Packages 5-7 Night Stays

Thompson Chicago
Fairmont Chicago at Millennium Park
Kimpton Gray Hotel, an IHG Hotel
Chicago Marriott Downtown Magnificent Mile

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Spirit Airlines

Discover Other Travel Deals


Prices are always lower in the app!

  • Book and go: Last-minute deals and trip details all in one place
  • Exclusive prices: Hot Rate® Hotels always cost less in the app
  • Fresh features: So slick you’ll never go back to desktop

Text yourself a download link

QR code