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.
Pendry Chicago
LondonHouse Chicago, Curio Collection by Hilton
Level Chicago – Old Town
Viceroy Chicago
Hilton Orrington / Evanston

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 $117 per night from Feb. 13 to Feb. 14
CA $117
CA $137 total
includes taxes & fees
Feb 13 - Feb 14
7.8/10 Good! (8,410 reviews)
"I would definitely stay here again. The queen roomis so spacious. There is a mini refrigerator, a safe, two bottles of complimentary bottles of water-nice. There is plenty of drawers to put your clothes in- thoughtful. The congress plaza hotel also included a coffee pot with coffee and tea-conveient. ..."

Reviewed on Jan. 22, 2025

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 $110 per night from Feb. 23 to Feb. 24
CA $110
CA $129 total
includes taxes & fees
Feb 23 - Feb 24
8.6/10 Excellent! (3,718 reviews)
"Enjoyed our stay. The hotel is a no frills hotel but the location is hard to beat right on the river. Our room had a fantastic view and was clean. We stayed two nights and both days housekeeping came around and refreshed towels and cleaned up. Overall we would come back to the River Hotel."

Reviewed on Jan. 21, 2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Feb. 23 to Feb. 24
CA $124
CA $146 total
includes taxes & fees
Feb 23 - Feb 24
8.6/10 Excellent! (2,804 reviews)
"I love the views"

Reviewed on Jan. 24, 2025

Eurostars Magnificent Mile
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 $778 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.