Hillside Vacation Packages 2026 from $392

Hillside flight + hotel vacation packages

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

The Buckingham Hotel

Downtown Chicago

Save 100% on your flight

$392

per person

Dec 9 - Dec 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a coffee shop, concierge services, and self parking. A 24-hour business center, a snack bar/deli, and luggage storage are also on offer.

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$791

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$694

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$729

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$623

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Top Hillside hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$127 total

Nov 2 - Nov 3

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

River Hotel

75 East Wacker Drive Chicago IL

$161 nightly

$191 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

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$170 total

Nov 1 - Nov 2

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

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

$151 nightly

$179 total

Nov 1 - Nov 2

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

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$227 total

Oct 30 - Oct 31

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

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$171 total

Nov 1 - Nov 2

Total with taxes and fees

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Spa

Free WiFi

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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 $392. 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.