Search Deals onHighland Vacation Packages
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Highland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites
Save 100% on your flight
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Chicago River Side Suites
Save 100% on your flight
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, daily housekeeping, and slippers. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Hilton Garden Inn Hoffman Estates
Save 100% on your flight
per person
Jul 10 - Jul 15
found 8 hours ago
Roundtrip flight included
Hartford (BDL) to Chicago (ORD)
Stay at this 3-star hotel in Hoffman Estates. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Bridges of Poplar Creek Country Club are located nearby.
Sofitel Chicago Magnificent Mile
Save 100% on your flight
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Art Institute of Chicago 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, Jul 8 - Tue, Jul 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 12 hours ago
$100
Roundtrip
found 12 hours ago
Sat, Jun 7 - Mon, Jun 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 7 hours ago
$188
Roundtrip
found 7 hours ago
Sat, Jul 12 - Wed, Jul 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$248 Roundtrip, just found
$248
Roundtrip
just found
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$889 Roundtrip, found 12 hours ago
$889
Roundtrip
found 12 hours ago
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