St. Augustine Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top St. Augustine vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $914
    CA $671
    per traveller
    found 1 hour ago
    Le Méridien Essex Chicago
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,009 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    Save 100% on your flight
    CA $1,899
    CA $1,337
    per traveller
    found 1 hour ago
    The Peninsula Chicago
  • Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,395
    CA $992
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 22 hours ago
    Park Hyatt Chicago
  • Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,344
    CA $984
    per traveller
    found 22 hours ago
    Pendry Chicago

St. Augustine Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a St. Augustine vacation package cost?

You can snap up a vacation package to this destination from CA $671 on Expedia. But how much your vacation to St. Augustine costs will depend on factors like the length of stay, hotel choice and season.

What are the cheapest months to go to St. Augustine?

If you're hoping to book a cheap St. Augustine vacation package, consider planning a trip in January, February and March. You're likely to find lower prices on accommodations and flights during these quieter months — perfect for a budget-friendly break.

How many days is enough for St. Augustine?

Generally, a handful of days is enough to see the major attractions during your St. Augustine vacation. However, if you prefer to have time to rest or go on day trips, consider extending your itinerary.

How to find the best St. Augustine package deals?

Bagging a cheap St. Augustine package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical St. Augustine package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.

Is it cheaper to book a St. Augustine vacation as a package?

An Expedia vacation package could land you significant savings when compared to booking flights and hotels individually. Better still, you can tailor your St. Augustine getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to St. Augustine?

Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment St. Augustine break.

How to plan a trip to St. Augustine?

  1. Pick your travel dates: What you plan to do in St. Augustine and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to St. Augustine.
  3. Decide how long to go for: Now that you're up to speed on St. Augustine, you can work out the right length of your vacation. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a St. Augustine vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.