Hillside Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Joe Farmer

  • Plan, book, travel with confidence

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    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Hillside Vacation Packages

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 NT$5,642 per night from Sep 14 to Sep 15
NT$5,642
NT$6,623 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (8,939 reviews)
"Friendly staff, clean rooms, huge hotel. Good location"

Reviewed on 2025/8/16

Congress Plaza Hotel
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 NT$4,529 per night from Sep 1 to Sep 2
NT$4,529
NT$5,317 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,187 reviews)
"Everything was great. Thanks for an awesome experience."

Reviewed on 2025/8/15

The Wade
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 NT$4,819 per night from Sep 3 to Sep 4
NT$4,819
NT$5,657 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,707 reviews)
"The Italian restaurant inside is delicious, we went twice! If you aren’t I. The mood for there are so many options that are walkable. The Taco spot around the corner is also a win for food Taco Maya. The only thing we didn’t like is having to wait so long for the elevator, 25 mins to get from the ..."

Reviewed on 2025/8/15

Embassy Suites by Hilton Chicago Downtown River North
See all 5,088 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.

Discover the most popular places to visit in Hillside

Wrigley Field featuring cbd, a sporting event and a city

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 showing night scenes, a city and signage

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 featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Frequently asked questions

How much does a Hillside vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Hillside costs! Our packages simplify travel planning and maximize 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 vacation 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 vacation. 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," "Traveler 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 vacation as a package?
An Expedia vacation 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 vacation 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 favorite 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 accommodations 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 vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.