Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Joe Farmer

Top hotels in Hillside

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is 3.982.323 ₫ per night from 1 Sept to 2 Sept
3.982.323 ₫
4.674.851 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug 2025

The Wade
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 4.960.761 ₫ per night from 14 Sept to 15 Sept
4.960.761 ₫
5.823.436 ₫ total
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is 4.021.172 ₫ per night from 3 Sept to 4 Sept
4.021.172 ₫
4.720.453 ₫ total
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,118 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

McCormick Place
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

Millennium Park

Frequently asked questions

How much does a Hillside holiday package cost?
Offering excellent value package deals 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?

  1. Choose your travel dates: What you'd like to do in Hillside and your favourite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.