Highland Hills Vacation Packages 2025 from $404

Highland Hills flight + hotel vacation packages

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

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

per person

Aug 4 - Aug 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A hair salon, WiFi in public areas, and luggage storage are also on offer.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 14 - Jul 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

per person

Aug 28 - Sep 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

Aug 28 - Sep 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.

La Banque Hotel

Save 100% on your flight

per person

Jul 12 - Jul 16

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

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

$99 nightly

$110 total

Jun 10 - Jun 11

Total includes 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

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free Cancellation

$118 nightly

$139 total

Jul 2 - Jul 3

Total includes 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

$203 nightly

$238 total

Jul 4 - Jul 5

Total includes 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

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave, Rosemont, IL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$148 total

Jun 15 - Jun 16

Total includes 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

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street, Chicago, IL

Free Cancellation

$136 nightly

$159 total

Jul 2 - Jul 3

Total includes taxes and fees

A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, express check-out, and laundry service.

Pool

Free WiFi

Grand Royal Hotel O'Hare - Chicago

1000 Busse Rd, Elk Grove Village, IL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Jun 15 - Jun 16

Total includes taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a terrace, and dry cleaning are also offered.

Parking included

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.

Navy Pier

4.5/5(4,870 reviews)

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

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

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 $404. 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.