Hillside Vacations from $572

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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.

The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $572 per person
$572
per person
Sep 5 - Sep 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,858 reviews)
Rooms were very bare. Ours didn’t even have a fridge, we had to ask for one. Then they gave us a beverage fridge. No dresser or storage anywhere. Bathroom had no counter space. Shower would get water everywhere because the curtain wasn’t long enough. Super tight space not worth the price.

Reviewed on Jul 30, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,721, price is now $996 per person
$996
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,125, price is now $734 per person
$734
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.

Reviewed on Jul 28, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,281, price is now $841 per person
$841
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,149, price is now $777 per person
$777
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

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What to do in Hillside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$42
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Hillside

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
$145 nightly
The price is $172 total per night from Aug 30 to Aug 31
$172 total
Aug 30 - Aug 31
Total with taxes and fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $181 total per night from Aug 11 to Aug 12
$181 total
Aug 11 - Aug 12
Total with taxes and fees
8/10 Very Good! (1,863 reviews)
"Towels and wash clothes leave white microfibers all over your skin and hair."

Reviewed on Jul 30, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$169 nightly
The price is $193 total per night from Aug 30 to Aug 31
$193 total
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Regency O'Hare Chicago
See all 4,978 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.

Find the Best Hillside Vacation Packages

Hillside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
8,200
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District

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Frequently asked questions

How much does a Hillside vacation package cost?
Offering excellent value package deals from $572 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?
November, December and January are the best times to search for cheap Hillside vacation packages. Choosing to travel in quieter periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Hillside?
The ideal duration for your Hillside vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to go to all the top attractions and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Hillside vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Hillside vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

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