Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
CA $747
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Hotel was perfect for the price. The room is kept nice but the Air conditioner was dirty, The toilet didn’t work well and the bathroom door never was never able to fully close. However it’s in a good area and if you don’t plan on staying in your hotel all day the room is fine. Just a bit dated. Overall 7/10
Reviewed on Aug 19, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,747
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,440
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
Ready to book your vacation to Hillside?
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $145
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,266 reviews)
"The hallways had peeling wallpaper and holes in the walls. The room was updated but not clean."
Reviewed on Aug 19, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $173
CA $206 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (2,045 reviews)
"The valet staff were excellent. The breakfast and drink vouchers make the hotel a great value. The breakfast is better than most hotels offer. The hotel is conveniently located to get to walking tours and other downtown attractions. Hotel staff are dedicated to meeting guest needs."
Reviewed on Aug 19, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $355
CA $417 total
Sep 12 - Sep 13
includes taxes & fees
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.
What to do in Hillside
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Hillside vacation package cost?
You can snap up a vacation package to this top destination from CA $747 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?
- Choose your travel dates: What you'd like to do in Hillside and your favourite season will help you decide when to travel.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
