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Highland Hills Vacation Packages

Highland Hills Flight + Hotel packages

Millennium Knickerbocker Chicago
Hampton Inn by Hilton Chicago-Midway Airport
Swissotel - Chicago
JW Marriott Chicago
21c Museum Hotel Chicago
Residence Inn by Marriott Chicago Downtown / River North
Springhill Suites by Marriott Chicago Downtown/ River North
Aloft Chicago Downtown River North
Prices and availability subject to change. Additional terms may apply.

3-4 Night Vacations in Highland Hills

Pendry Chicago
JW Marriott Chicago
Fairmont Chicago at Millennium Park Gold Experience
Trump International Hotel & Tower Chicago
Prices and availability subject to change. Additional terms may apply.

5-7 Night Vacations in Highland Hills

The Westin Michigan Avenue Chicago
LondonHouse Chicago, Curio Collection by Hilton
Pendry Chicago
The Peninsula Chicago
Prices and availability subject to change. Additional terms may apply.

Cheap Hotel Deals in Highland Hills

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street, Lombard, IL
Stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free parking, and WiFi. Our guests praise the breakfast and the helpful staff in our reviews. ...
SureStay Plus Hotel by Best Western Chicago Lombard
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the pool and the helpful staff in our reviews. ...
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3 out of 5
1 S Franklin Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Chicago Downtown
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
28 North Franklin Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Hyatt Place Chicago/Downtown - The Loop
voco Chicago Downtown, an IHG Hotel

voco Chicago Downtown, an IHG Hotel

3.5 out of 5
350 W Wolf Point Plaza Building, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the breakfast and the pool ...
voco Chicago Downtown, an IHG Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast, and WiFi. Our guests praise the clean rooms in our reviews. Popular attractions ...
Hilton Chicago O'Hare Airport
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
6810 Mannheim Rd, Rosemont, IL
Stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean ...
Hyatt Place Chicago/O'Hare Airport
Hotel Chicago West Loop

Hotel Chicago West Loop

2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and onsite parking. Our guests praise the helpful staff and the clean ...
Hotel Chicago West Loop
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Frontier Airlines
Scandinavian Airlines
United

Find cheap hotels in Highland Hills

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Highland Hills hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Highland Hills.

Choosing the right hotel in Illinois has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Highland Hills’s 2,747 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $76. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Highland Hills hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Highland Hills. No matter your reason for visiting Highland Hills, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Highland Hills hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Highland Hills for as low as $76.

How many hotels are there in Highland Hills?

With over 2,747 hotels in Highland Hills, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $76.

How to find cheap car rentals in Highland Hills?

Finding a cheap car rental deal in Chicago is as easy as scoring cheap hotels in Highland Hills. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Highland Hills now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Highland Hills right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.