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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $435, price is now $316 per person
$316
per person
Nov 23 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hair salon, express check-in, and express check-out are also on offer.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,328, price is now $860 per person
$860
per person
Nov 28 - Dec 1
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $983, price is now $665 per person
$665
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,312, price is now $921 per person
$921
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $948, price is now $679 per person
$679
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.

Top Hillside hotels deals

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $221 total per night
$221 total
Oct 25 - Oct 26
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
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
$157 nightly
The price is $187 total per night
$187 total
Oct 26 - Oct 27
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
$179 nightly
The price is $213 total per night
$213 total
Oct 14 - Oct 15
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
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $251 total per night
$251 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and valet parking. Enjoy the free continental breakfast each morning. Express check-in, express check-out, and a computer station are also on offer.
Breakfast included
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
$179 nightly
The price is $213 total per night
$213 total
Oct 25 - Oct 26
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
$185 nightly
The price is $220 total per night
$220 total
Oct 24 - Oct 25
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 $316. 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 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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