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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,483, price is now CA $994 per person
CA $994
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Excellent spot, in the perfect location. Parking at the property is pretty expensive, but there are cheaper parking garages close by.

Reviewed on Jul 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,057, price is now CA $1,243 per person
CA $1,243
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,648, price is now CA $1,089 per person
CA $1,089
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
A hidden gem in the heart of the Gold Coast! Wonderful staff! Shout out to Steve! He made us feel right at home! Coffee machines in the room were amazing, the coffee was delicious! Thank you to all the staff for all that they do! Til next time!

Reviewed on Jul 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on Jul 6, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,167, price is now CA $1,473 per person
CA $1,473
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Vas room, AC was broken, lots of dust … Old

Reviewed on Jul 7, 2026

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Hickory Hills Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jul 27 to Jul 28
CA $233
CA $277 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,701 reviews)
"HIDDEN FEES WILL CHARGE DOUBLE"

Reviewed on Jul 6, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Jul 9 to Jul 10
CA $240
CA $332 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (1,866 reviews)
"Vas room, AC was broken, lots of dust … Old"

Reviewed on Jul 7, 2026

Omni Chicago Hotel
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 $231 per night from Jul 8 to Jul 9
CA $231
CA $275 total
Jul 8 - Jul 9
includes taxes & fees
8/10 Very good! (10,194 reviews)
"Bartender, Chris was very nice!"

Reviewed on Jul 6, 2026

Congress Plaza Hotel
See all 4,434 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.
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What to do in Hickory Hills

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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 $994 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.

Explore a world of travel with Expedia

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