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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 23 - Oct 26
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
The Emily was a super nice hotel with very friendly staff and conveniently located near lots of restaurants and bars

Reviewed on Aug. 5, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
The location of the hotel right off Michigan Avenue was perfect. Public parking right across the street. The hotel is fresh and new. Many staff available to assist. Do not skip the complimentary breakfast! I would easy pay $20 for that breakfast as it had everything from fresh fruit, real eggs, pastries, even a coffee cream warmer/frother machine for the great coffee!

Reviewed on Aug. 6, 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
Oct 10 - Oct 15
found 1 day 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

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Communication was great. Offered upgrade immediately and also had gift at check in for my husband, it was his birthday. Very nice staff. Johnnie at front desk was excellent. Very kind.

Reviewed on Aug. 6, 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! (8,981 reviews)
"I love it"

Reviewed on Aug. 5, 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 22 to Aug 23
CA $239
CA $315 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,830 reviews)
"Love the gym!"

Reviewed on Aug. 5, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,351 reviews)
"I liked the in and out parking access for one rate per day."

Reviewed on Aug. 6, 2025

Crowne Plaza Chicago West Loop by IHG
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 $922 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.