Hickory Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on Jul. 7, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Ready to book your vacation to Hickory Hills?

 

Choose your dates

Hickory Hills Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,957 reviews)
"Good stay"

Reviewed on Jul. 13, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $273 per night from Aug 10 to Aug 11
CA $273
CA $364 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,031 reviews)
"Great location ! Small but nice room ."

Reviewed on Jul. 13, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 10 to Aug 11
CA $207
CA $243 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul. 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,479 properties in Hickory Hills
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Hickory Hills

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Hickory Hills

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Hickory Hills

Frequently asked questions

How much does a Hickory Hills vacation package cost?
Offering excellent value package deals from CA $688 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.