Hillside Vacation Packages

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Your Hillside Vacation

An easy way to experience this vibrant city is with a custom-made Hillside vacation package. Base yourself in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with major attractions such as Brookfield Zoo, Oakbrook Center Mall and Yorktown Shopping Center. Expedia can help you escape the everyday. Tailor your vacation to Hillside to suit your style of travel, whatever that may be.

Top Hillside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.8/10 Excellent! (2,544 reviews)
The Views of Chicago river and Lake Michigan are Fab!!!!!

Reviewed on Aug. 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Experience was incredible and in proximity to magnificent mile

Reviewed on Aug. 10, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on Aug. 11, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 24 - Oct 28
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
it was good, easy access to lollapalooza

Reviewed on Aug. 10, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

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Hillside 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 $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,926 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on Aug. 8, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $314 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,836 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on Aug. 8, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Aug 24 to Aug 25
CA $211
CA $248 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (3,648 reviews)
"Good"

Reviewed on Aug. 10, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,072 properties in Hillside
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 Hillside

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

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

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
Navy Pier

Navy Pier

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

Navy Pier

What to do in Hillside

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Hillside

Frequently asked questions

How much does a Hillside vacation package cost?
You can snap up a vacation package to this top destination from CA $716 on Expedia. However, how much your vacation to Hillside costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Hillside?
You can generally find lower rates and better availability in December, January and February. Browse our cheap Hillside vacation packages and you could land some great off-season discounts.
How many days is enough for Hillside?
Dedicate at least 2 days for your Hillside vacation if you want to immerse yourself in everything that makes this place special. Explore popular neighbourhoods, including Yorkfield and York Centre. Then tick off major sights such as Unity Temple and Galloping Ghost. With a good itinerary, you can keep busy with room for some relaxation too. Want to venture beyond Hillside? Consider fitting in an excursion or two.
How to find the best Hillside package deals?
Use Expedia's filter tool to find some fabulous Hillside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Hillside package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Hillside vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Hillside vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Hillside?
Secure amazing discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Hillside break.
How to plan a trip to Hillside?

  1. Choose your travel dates: What you'd like to do in Hillside and your favourite season will help you decide when to travel.
  2. Budget wisely: Besides the price of your stay, you'll need to consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Hillside.
  3. Decide how long to go away for: Now that you know more about Hillside, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Hillside 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.