Hickory Hills Vacation Packages
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Your Hickory Hills Vacation
When a fun city getaway is calling, answer it with a vacation package to Hickory Hills. The neighborhood of Woodlawn, which is great for cycling, golfing and walking, makes a terrific base for your adventures. Want to explore your surroundings? SeatGeek Stadium, Chicago Ridge Shopping Mall and Burr Ridge Village Center are three of the leading places to visit during your trip to Hickory Hills. A couple of quick clicks is all it takes to build your dream Hickory Hills vacation on Expedia.
Top Hickory Hills Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $2,124
per person
Nov 19 - Nov 24
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 2026
Ready to book your vacation to Hickory Hills?
Hickory Hills Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $165
CA $196 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very good! (10,213 reviews)
"When I first walked in to the hotel, I was impressed by the beautiful lobby. But that was it. The rooms are extremely dated, the bathtub has rust all over, and the door frames have huge dents. Yes, they do have nice high ceilings, but the furniture needs to be updated, and the windows need room darkening ..."
Reviewed on Oct 7, 2026
River Hotel
75 East Wacker Drive Chicago IL
CA $237
CA $282 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (5,483 reviews)
"Clean and very helpful staff. Great location!"
Reviewed on Oct 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $203
CA $242 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (2,429 reviews)
"N/A"
Reviewed on Oct 7, 2026
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.
What to do in Hickory Hills
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Hickory Hills vacation package cost?
Offering excellent value package deals from CA $1,047 on Expedia, you'll be pleasantly surprised at how much a vacation to Hickory Hills costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Hickory Hills?
The off-season is the best time to head to Hickory Hills if you're trying to save. Another tip for finding cheap Hickory Hills vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Hickory Hills?
We recommend booking a Hickory Hills vacation for a minimum of 5 days. This will give you enough time to check off top attractions such as Moraine Valley Community College Fine and Performing Arts Centre and Lake Katherine Nature Centre, as well as explore neighbourhoods like Clearing and Ashburn. You could even make time for a day trip or two outside of Hickory Hills.
How to find the best Hickory Hills package deals?
Begin your search for a Hickory Hills package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Hickory Hills package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hickory Hills getaway off to a flying start.
Is it cheaper to book a Hickory Hills vacation as a package?
You can enjoy significant savings on your Hickory Hills getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Hickory Hills?
If you have your Hickory Hills travel dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Hickory Hills?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Hickory Hills.
- Set your budget: Consider costs like transportation, flights and meals when calculating how much to set aside for your trip to Hickory Hills. Then, choose a property that fits your budget, whether that's a low-cost stay or a more upscale getaway.
- Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Hickory Hills. Then, estimate how long you'll need at each, including any travel time.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Hickory Hills 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.
