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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,405 reviews)
We try to stay here every time we come to Chicago.

Reviewed on Aug. 3, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
I booked a room with the water view, when I checked in I asked before I get the key, Is it a water view. They told me it is. I show up in my room and it’s not the room I booked. I called the front desk and they’re telling me we apologize all of the rooms are booked with the water view. They also said booking a water view room doesn’t guarantee a water view room even though I paid extra for a water view room! Never going to stay there again for sure.

Reviewed on Aug. 3, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 2025

Ready to book your vacation to Hillside?

 

Choose your dates

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! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug. 1, 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 $281 per night from Sep 1 to Sep 2
CA $281
CA $374 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (2,150 reviews)
"Loved this hotel. We had a king classic in grand tower high floor. Our bed was comfy, shower was nice, room was large enough and loved the colors. View was decent. Bar had great drinks. Pool is gorgeous. The only negative was the elevators which were compact and wait times were very long sometimes. ..."

Reviewed on Aug. 1, 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 $198 per night from Aug 17 to Aug 18
CA $198
CA $233 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,564 reviews)
"Nice clean hotel, good location."

Reviewed on Aug. 2, 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,191 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.
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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
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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 $862 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.