Hillside Vacation Packages 2026 from $327

Hillside flight + hotel vacation packages

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

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

Save 100% on your flight

$327

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This smoke-free hotel's 2 restaurants, 3 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. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$328

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

$546

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

A full-service spa, an indoor pool, 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 gym, bar/lounge, and laundry facilities.

La Banque Hotel

Save 100% on your flight

$432

per person

Feb 22 - Feb 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

$332

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Top Hillside hotels deals

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$182 total

Feb 1 - Feb 2

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.

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$101 total

Jan 25 - Jan 26

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$103 total

Jan 30 - Jan 31

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. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$193 total

Jan 21 - Jan 22

Total with taxes and fees

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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$110 total

Jan 21 - Jan 22

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$209 total

Feb 1 - Feb 2

Total with taxes and fees

This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.

Free WiFi

Restaurant

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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.

Popular places to visit

Wrigley Field

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

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier

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

Frequently asked questions

How much are vacation packages to Hillside?

Your travel fantasies can become a reality in Hillside from an impressive $327. 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.