Search Deals onHighland Vacation Packages
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Highland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Des Plaines Motel By OYO O'Hare Airport Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Des Plaines. Enjoy free WiFi, free parking, and room service. Popular attractions Allstate Arena and Lake Park are located nearby.
Chicago Athletic Association, a Hyatt Hotel
Save 100% on your flight
per person
Aug 16 - Aug 21
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 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
Arlo Chicago
Save 100% on your flight
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
HYATT house Chicago/Schaumburg
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and FireZone are located nearby.
The Chicago Hotel Collection - Wrigleyville
Save 100% on your flight
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
DoubleTree by Hilton Lisle Naperville
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Sea Lion Aquatic Park are located nearby.
Urban Chicago Oasis
Save 100% on your flight
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Motel Edgebrook Chicago North Shore by OYO
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Allstate Arena and Milwaukee Avenue 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.
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 4 hours ago
$130
Roundtrip
found 4 hours ago
Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 13 hours ago
$255
Roundtrip
found 13 hours ago
Fri, Aug 22 - Sat, Sep 6
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$527 Roundtrip, found 1 day ago
$527
Roundtrip
found 1 day ago
Fri, Nov 7 - Sun, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$994 Roundtrip, found 1 day ago
$994
Roundtrip
found 1 day ago
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