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Highland Hills Vacation Packages

Highland Hills Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) 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 in our reviews. Popular attractions Michigan Avenue and Millennium 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
Feb 27 - Mar 3
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
Kimpton Gray Hotel, an IHG Hotel

Kimpton Gray Hotel, an IHG Hotel

4.5 out of 5
Downtown Chicago
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 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 Millennium Park are located nearby.

3-4 Night Vacations in Highland Hills

Price found within the past 48 hours. Click for updated prices.
Extended Stay America Suites Chicago O'Hare Allstate Arena

Extended Stay America Suites Chicago O'Hare Allstate Arena

2.5 out of 5
O'Hare
per person
Feb 27 - Mar 2
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)

Woodspring Suites Loves Park Rockford

2.5 out of 5
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
per person
Feb 14 - Feb 17
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Carleton of Oak Park

Carleton of Oak Park

3 out of 5
per person
Mar 9 - Mar 12
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

5-7 Night Vacations in Highland Hills

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

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 19 - Feb 24
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) 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 parking, and a fitness center. Our guests praise the breakfast and the helpful ...
SureStay Plus Hotel by Best Western Chicago Lombard
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn Chicago-O'Hare International Airport
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 (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
voco Chicago Downtown, an IHG Hotel
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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
Chicago Getaway Hostel

Chicago Getaway Hostel

2 out of 5
616 W Arlington Pl, Chicago, IL
Stay at this hostel in Chicago. Enjoy parking (surcharge), a 24-hour front desk, and a business center. Our guests praise the breakfast and the helpful staff ...
Chicago Getaway Hostel
Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel

Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel

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, an IHG Hotel
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
Marriott Chicago O'Hare
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 WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
Hyatt Place Chicago/Downtown - The 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.

Frontier Airlines
Mon, Jan 27 - Mon, Feb 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jan 27 from Los Angeles Intl. to Midway Intl., returning Mon, Feb 3, priced at $120 found 2 days ago
Frontier Airlines
Mon, Jan 27 - Sat, Feb 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jan 27 from Los Angeles Intl. to O'Hare Intl., returning Sat, Feb 1, priced at $120 found 1 day ago
Icelandair
Thu, Mar 20 - Tue, Apr 1
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$554 Roundtrip, found 2 days ago
$554
Roundtrip
found 2 days ago
Select Icelandair flight, departing Thu, Mar 20 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $554 found 2 days ago
Cathay Pacific
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,191 Roundtrip, found 1 day ago
$1,191
Roundtrip
found 1 day ago
Select Cathay Pacific flight, departing Tue, Feb 25 from Pudong Intl. to O'Hare Intl., returning Sun, Mar 2, priced at $1,191 found 1 day ago