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.
Level Chicago - River North
Level Chicago – Old Town
Swissotel - Chicago
Waldorf Astoria Chicago
Hotel Riu Plaza Chicago

Ready to book your vacation to Hillside?

 

Choose your dates

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 $150 per night from Jan. 1 to Jan. 2
CA $150
CA $176 total
includes taxes & fees
Jan 1 - Jan 2, 2025
7.8/10 Good! (8,267 reviews)
"The hotel is very historic and beautifully decorated. We had a junior suite that was extremely roomy and very clean. The furniture was nice, but didn’t seem to match the historic charm of the hotel being that the decor in the room was ultra modern. The bathroom was huge, but the tub wasn’t updated ..."

Reviewed on Dec. 24, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jan. 6 to Jan. 7
CA $149
CA $175 total
includes taxes & fees
Jan 6 - Jan 7, 2025
8.6/10 Excellent! (3,626 reviews)
"Having to park my car 4 blocks away"

Reviewed on Dec. 22, 2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jan. 19 to Jan. 20
CA $212
CA $291 total
includes taxes & fees
Jan 19 - Jan 20, 2025
9/10 Wonderful! (3,120 reviews)
"really enjoyed the city view from room."

Reviewed on Dec. 20, 2024

Hyatt Regency Chicago
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.

Frequently asked questions

How much does a Hillside vacation package cost?
Offering excellent value package deals from CA $727 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.

Discover the most popular places to visit in Hillside

What to do in Hillside

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