Hillside Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Hillside
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
€849
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
I wish I could have better things to say about the hotel, but for the nearly $1600 we paid for marathon weekend, I would've liked a clean bathroom and not feeling like we were in a 1 star lower Manhattan find (while still being in Chicago). The bed was comfortable at least!
Reviewed on 13 Oct 2026
Top hotels in Hillside
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€123
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,179 reviews)
"It has a beautiful lobby. Our two queen bed room had big beautiful windows. The only odd thing about the room was the ledge that you had to step over to get to the bathroom. Not a deal breaker for a historic hotel."
Reviewed on 13 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€162
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,534 reviews)
"I absolutely loved this place. Close to everything and great view"
Reviewed on 12 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€152
4 Nov - 5 Nov
includes taxes & fees
8/10 Very good! (2,494 reviews)
"Great location, short walking distance from Lincoln Park and the lake on one side, and the red line metro station on the other side. The neighborhood gives a British feel on N State Street. The Hotel is very quiet. My room was very spacious (King) and felt recently remodeled (except for the bathroom ..."
Reviewed on 13 Oct 2026
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
Wendella's 90-min Chicago River Architecture Tour
€36
per adult
94% of travellers recommend
Frequently asked questions
How much does a Hillside holiday package cost?
Offering excellent value package deals from €849 on Expedia, you'll be thrilled with how little a holiday to Hillside costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Hillside?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Hillside holiday packages and you could get some great off-season discounts.
How many days is enough for Hillside?
Typically, a handful of days is enough to check out the top attractions during your Hillside holiday. But if you'd like to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Hillside package deals?
Landing a cheap Hillside package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Hillside package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Hillside holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Hillside escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Hillside?
If you're considering an impromptu Hillside getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Hillside?
- Choose your travel dates: What you'd like to do in Hillside and your favourite season can help you decide when to travel.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your accommodation will likely be the biggest expense during your trip to Hillside.
- Decide how long to go away for: Now that you're more familiar with Hillside, you can figure out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Hillside holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
