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Highland Hills Vacation Packages

Highland Hills Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago North Shore/Evanston

Hilton Garden Inn Chicago North Shore/Evanston

3.5 out of 5
Downtown Evanston
Save 100% on your flight
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Baha'i House of Worship and Aragon Ballroom are located nearby.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Jul 17 - Jul 21
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.

3-4 Night Vacations in Highland Hills

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
per person
Jul 31 - Aug 3
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)

5-7 Night Vacations in Highland Hills

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

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip flight included
Boston (BOS) 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
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
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
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Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
Holiday Inn & Suites Chicago - Downtown by IHG
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Grand Royal Hotel O'Hare - Chicago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
Stay at this 3.5-star business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk 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 - Riverwalk by IHG
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
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, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 10 hours ago
$150
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Mon, Jul 7 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $150 found 10 hours ago
Delta
Mon, Jul 14 - Tue, Jul 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, found 2 hours ago
$257
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Jul 14 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 15, priced at $257 found 2 hours ago
Icelandair
Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$583 Roundtrip, found 2 days ago
$583
Roundtrip
found 2 days ago
Select Icelandair flight, departing Tue, Aug 26 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Sep 2, priced at $583 found 2 days ago
Delta
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$966 Roundtrip, found 2 days ago
$966
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jun 19 from Hong Kong Intl. to O'Hare Intl., returning Mon, Aug 4, priced at $966 found 2 days ago