Rose Hill 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

Your Rose Hill Vacation

Entertainment, history, art and more … It's all waiting for you with a Rose Hill vacation package. And with the ability to easily customize your city adventure, you know it'll be one that's tough to forget. Not sure what to do or see first during your trip to Rose Hill? Head for famous attractions such as Lake Keomah State Park. Expedia has what you need to escape your routine. Tailor your vacation to Rose Hill to suit your style of travel, whatever that may be.

Top Rose Hill 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 day ago
    Le Méridien Essex 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
    Save 100% on your flight
    CA $1,353
    CA $941
    per traveller
    found 1 day ago
    Pendry Chicago
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,012 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 day ago
    The Peninsula Chicago
  • Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,880 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,107
    CA $794
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,782 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,284
    CA $938
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

Rose Hill 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 Rose Hill vacation package cost?

Offering great value package deals from CA $671 on Expedia, you'll be surprised at how little a vacation to Rose Hill costs! Expedia's packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Rose Hill?

You can typically find lower rates and greater availability in January, February and March. Take a look at our cheap Rose Hill vacation packages and you could score some excellent off-season deals.

How many days is enough for Rose Hill?

Usually, a handful of days is enough to check out the main sights during your Rose Hill vacation. However, if you prefer to have some time to chill out or take day trips, consider extending your trip.

How to find the best Rose Hill package deals?

Use Expedia's filters to help you find some of the best Rose Hill package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Rose Hill package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.

Is it cheaper to book a Rose Hill vacation as a package?

You can enjoy significant savings on your next Rose Hill getaway by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Rose Hill?

If you're considering an impromptu Rose Hill trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.

How to plan a trip to Rose Hill?

  1. Choose when to get away: Check your schedule and get packing. Your favourite time of year and the available activities will also help you decide when to vacation in Rose Hill.
  2. Set your budget: Factor in expenses such as flights, transportation and food when working out how much to save for your trip to Rose Hill. Then, choose a property that matches your budget, whether that's a wallet-friendly option or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Rose Hill. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Rose Hill vacation package.

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