Hillside Vacations from $577

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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 Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $879, price is now $577 per person
$577
per person
Aug 5 - Aug 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,954 reviews)
The staff was able to help us get a room earlier than the check-in time.

Reviewed on Jun 9, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,446, price is now $885 per person
$885
per person
Aug 5 - Aug 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $955, price is now $612 per person
$612
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Perfect location, large breakfast buffet included, great restaurants and shopping nearby, would return there without any hesitation!

Reviewed on Jun 9, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,209, price is now $790 per person
$790
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic

Reviewed on Jun 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $718 per person
$718
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,119 reviews)
Staff was amazing. Great hotel and location!

Reviewed on Jun 8, 2026

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Discover the most popular places to visit in Hillside

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

What to do in Hillside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$154
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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
$136 nightly
The price is $162 total per night from Jun 30 to Jul 1
$162 total
Jun 30 - Jul 1
Total with taxes and fees
8/10 Very Good! (10,228 reviews)
"Housekeeping did not come a single time in the four days and four nights I stayed there. The beds were not made nor was the trash taken out a single time . I had to phone them twice to receive bath towels. I was using Uber eats take out bags as trash bags due to the lack of housekeeping not ..."

Reviewed on Jun 9, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$162 nightly
The price is $192 total per night from Jul 1 to Jul 2
$192 total
Jul 1 - Jul 2
Total with taxes and fees
7.8/10 Good! (1,547 reviews)
"Everything perfect"

Reviewed on Jun 9, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."

Reviewed on Jun 9, 2026

Hyatt Regency O'Hare Chicago
See all 5,065 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 $577 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.