Highland Hills Vacation Packages 2025/2026 from $231

Highland Hills flight + hotel vacation packages

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

Illinois Beach Hotel

Save 100% on your flight

$231

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

New Orleans (MSY) to Chicago (ORD)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$335

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

La Banque Hotel

Save 100% on your flight

$355

per person

Oct 13 - Oct 16

just found

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$982

per person

Nov 10 - Nov 14

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.

Villa Dubois Guest House

Bronzeville

Save 100% on your flight

$429

per person

Nov 27 - Dec 4

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Chicago (ORD)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a communal living room, and express check-in are also on offer.

Top Highland Hills hotels deals

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street, Lombard, IL

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$100 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Breakfast included

Parking included

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave, Rosemont, IL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$163 total

Sep 20 - Sep 21

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 business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.

Free airport shuttle

Pet friendly

Marriott Chicago O'Hare

8535 West Higgins Road, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$179 total

Sep 19 - Sep 20

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's an indoor pool on site, and a 24-hour front desk and a coffee shop are also provided.

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free Cancellation

$202 nightly

$237 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

Hilton Chicago O'Hare Airport

O'Hare International Airport, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$210 total

Oct 4 - Oct 5

Total with taxes and fees

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.

Free airport shuttle

Pet friendly

Canopy by Hilton Chicago Central Loop

226 West Jackson Blvd, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$221 nightly

$259 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking and a snack bar/deli are also offered on site.

Pet friendly

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.

Popular places to visit

Wrigley Field

4.5/5(2,128 reviews)

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

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

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

4.5/5(4,870 reviews)

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

Frequently asked questions

How much are vacation packages to Highland Hills?

With Travelocity vacation packages, you can experience the sights and sounds of Highland Hills for as low as $231. Activities, flights and hotels — we have everything you need. You'll save loads just for combining your bookings. And with all of that taken care of before you even set off, you can sit back, relax and enjoy the adventure.

How long should my Highland Hills vacation be?

Generally, visitors spend 2 nights in Highland Hills. However, that might not be enough time for you. If you'd like to see some of the region's off-the-beaten-path treasures, how about adding another couple of nights to your travel itinerary?

Where can I get the best vacation package deals for Highland Hills?

Travelocity has all you need to score an amazing Highland Hills package deal. Select from 400 partner airlines and 1,000,000 properties all over the world and put together a travel itinerary that's right for you. With so much choice, it's time to start planning your next big adventure.

Why should I book my Highland Hills vacation package via Travelocity?

Travel is all about making fantastic new memories and forgetting all your worries — which is why we provide you with a friendly team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our superb range of package deals. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.

Will I save money on my Highland Hills car rental if I book it with hotels and flights?

With a Highland Hills vacation package, you can bundle your flight, hotel and car bookings and save loads. When you're ready to explore the best of this fabulous region, why not check out Six Flags Great America? This well-known sight is 35 mi from Highland Hills. With a rental car, you'll be there in no time.

Which airport is best for Highland Hills?

It's very likely you'll land at O'Hare Intl. Airport (ORD), located 10 mi northeast of inner Highland Hills. Midway Intl. Airport (MDW) (14 mi away from central Highland Hills) and Rockford, IL (RFD-Greater Rockford) (60 mi away from central Highland Hills) are your other choices.

Where should I stay when visiting Highland Hills?

The SureStay Plus Hotel by Best Western Chicago Lombard is the top choice of many visitors. Book now to avoid missing out.