Search Deals onHighland Vacation Packages
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Highland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
MainStay Suites Chicago Schaumburg
per person
May 5 - May 7
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this hotel in Schaumburg. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and AMC Streets Of Woodfield 20 are located nearby.
Chicago Marriott Suites Deerfield
per person
May 17 - May 19
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Deerfield. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sportsman's Country Club and Chevy Chase Country Club are located nearby.
Hyatt Place Chicago/Downtown - The Loop
per person
Mar 29 - Mar 31
found 10 hours ago
Roundtrip non-stop flight included
New York (JFK) to Chicago (ORD)
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 and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Fairmont Chicago at Millennium Park
Save 100% on your flight
per person
Apr 6 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa 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 Chicago Riverwalk are located nearby.
Courtyard Chicago Waukegan Gurnee
per person
May 17 - May 19
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Waukegan. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Six Flags Great America and The Temporary by American Place are located nearby.
Super Sleep Inn By OYO I-80 Princeton
Save 100% on your flight
per person
Apr 1 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this motel in Princeton. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Bureau County Fairgrounds and Soldiers and Sailors Memorial are located nearby.
Highland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Highland Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Tue, Apr 8 - Wed, Apr 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Mon, May 19 - Sat, May 24
LAX
Los Angeles Intl.
MDW
Midway Intl.
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,114 Roundtrip, found 6 days ago
$1,114
Roundtrip
found 6 days ago
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