Search Deals onHighland Vacation Packages
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Highland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Stella Hotel & Ballroom
Save 100% on your flight
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
Stay at this 3.5-star business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dinosaur Discovery Museum and Alpaca Art are located nearby.
Park Hyatt Chicago
Save 100% on your flight
per person
Oct 14 - Oct 18
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
La Banque Hotel
Save 100% on your flight
per person
Oct 2 - Oct 5
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
per person
Oct 3 - Oct 5
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.
The Wade
Save 100% on your flight
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
DayDreamer Domes
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star hotel in South Haven. Enjoy free parking, room service, and onsite spa services. Popular attractions Kal Haven Trail and Michigan Maritime Museum are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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.
Sat, Aug 16 - Tue, Aug 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Sat, Oct 25 - Sat, Oct 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Wed, Aug 27 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$620 Roundtrip, found 4 days ago
$620
Roundtrip
found 4 days ago
Mon, Sep 22 - Sat, Oct 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$849 Roundtrip, found 4 days ago
$849
Roundtrip
found 4 days ago
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