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Highland Hills Vacation Packages

Highland Hills Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
O'Hare
Save 100% on your flight
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Pirates Cove Childrens Theme Park are located nearby.
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Downtown Chicago
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy a sauna, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Grant Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
O'Hare
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and the bar in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
O'Hare
Save 100% on your flight
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.

3-4 Night Vacations in Highland Hills

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

Alpine Inn Rockford

2.5 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Days Inn by Wyndham Rockford I-90 Casino District

Days Inn by Wyndham Rockford I-90 Casino District

2.5 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Super 8 by Wyndham Rochelle

Super 8 by Wyndham Rochelle

2 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Super 8 by Wyndham DeKalb IL

Super 8 by Wyndham DeKalb IL

2 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Highland Hills

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 12 hours ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 12 hours ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 12 hours ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

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
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
SureStay Plus Hotel by Best Western Chicago Lombard
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Crowne Plaza Chicago West Loop by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Hyatt Regency O'Hare Chicago
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Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hyatt Regency Schaumburg Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hilton Chicago O'Hare Airport
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 2 restaurants. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Chicago Downtown
voco Chicago Downtown by IHG

voco Chicago Downtown by IHG

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 (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
voco Chicago Downtown by IHG
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn - The Mart by IHG
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
Mon, May 5 - Sat, May 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, May 5 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 10, priced at $96 found 1 day ago
Frontier Airlines
Mon, May 19 - Sat, May 24
LAX
Los Angeles Intl.
MDW
Midway Intl.
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, May 19 from Los Angeles Intl. to Midway Intl., returning Sat, May 24, priced at $220 found 5 days ago
ITA Airways
Fri, Aug 22 - Sat, Sep 6
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$673 Roundtrip, found 19 hours ago
$673
Roundtrip
found 19 hours ago
Select ITA Airways flight, departing Fri, Aug 22 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $673 found 19 hours ago
United
Sun, Jun 29 - Sun, Aug 31
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,011 Roundtrip, found 2 days ago
$1,011
Roundtrip
found 2 days ago
Select United flight, departing Sun, Jun 29 from Hong Kong Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $1,011 found 2 days ago