Deals on vacations and trips to Hillside

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Hillside flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $883, price is now $633 per person
$633
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,353, price is now $924 per person
$924
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,305, price is now $922 per person
$922
per person
Jan 27 - Jan 31
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $2,031, price is now $1,469 per person
$1,469
per person
Jan 21 - Jan 26
found 11 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,065, price is now $773 per person
$773
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Hillside hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $127 total per night
$127 total
Nov 22 - Nov 23
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$187 nightly
The price is $195 total per night
$195 total
Dec 8 - Dec 9
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$106 nightly
The price is $126 total per night
$126 total
Dec 10 - Dec 11
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $141 total per night
$141 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.
Pool
Pet friendly
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $138 total per night
$138 total
Nov 22 - Nov 23
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.
Pet friendly
Free WiFi
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$162 nightly
The price is $190 total per night
$190 total
Nov 27 - Nov 28
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Pool
Hot Tub
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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 are vacation packages to Hillside?
Your travel fantasies can become a reality in Hillside from an impressive $633. Vacation packages include flights and hotels, so organizing everything should be nice and easy. The only thing you'll need to concentrate on is getting out there and having a great time.
How long should my Hillside vacation be?
Most people spend roughly 2 nights in Hillside, but it's your call. If you want to venture out and explore all the amazing things this place has to offer, why not hang around another couple of nights?
Where can I get the best vacation package deals for Hillside?
There's no need to look any further than Travelocity. With as many as 400 airlines and 1,000,000 properties around the world, it's easy to find a Hillside package deal that suits your needs.
Why should I purchase my Hillside vacation package with Travelocity?
We make traveling the world easy. Whether you're seeking an amazing new place to uncover or want to ensure you get the best price on offer, we've got your back. Our 24/7 support, top-quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Can I save money on my Hillside car rental if I book it with my hotel or flight?
Combining your car, hotel and flight into a Hillside vacation package is the easiest way to land the best deal. Plus, having your own car rental gives you freedom to get to all those amazing sights you'd like to check out. Situated 35 mi from Hillside, Six Flags Great America is one place that should feature on your itinerary. Put together a driving playlist and make a day trip of it.
Which airport is best for Hillside?
O'Hare Intl. Airport (ORD) is one of the biggest airports in Hillside. It's located 7 mi north of the city center. Your other options are Midway Intl. Airport (MDW) (10 mi away from central Hillside) and Lewis University Airport (LOT) (20 mi away from central Hillside).
What is there to do in Hillside?
Enjoy some great photo-ops at Fresh Meadow Golf Club, one of the most renowned attractions in Hillside. There's a lot more to discover in this exciting destination, so give yourself enough time to visit some of its off-the-beaten-path gems.
Where should I stay when visiting Hillside?
Many travelers opt to check in to the Holiday Inn Express & Suites Chicago West - OHare Arpt Area. It's a great base for your Hillside getaway.

Photos of local treasures

Browse Hillside vacation photos for more inspiration

A lush green valley with a winding road, steep mountains, and a misty atmosphere.
A mountainous landscape with dense forests and a grassy meadow.
A cemetery with a prominent tombstone labeled "CAPONE" in the center.
A grave with a name plaque and a rifle.
A gravestone with the name Alphonse Capone, birth and death years, and the phrase "My Jesus Mercy".

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