Search Deals onHighland Vacation Packages
Photo by Joe Farmer
Highland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Save 100% on your flight
Price was $519, price is now $288 per person
$288
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Art Villa
Save 100% on your flight
Price was $1,004, price is now $473 per person
$473
per person
Dec 31 - Jan 3
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,082, price is now $591 per person
$591
per person
Nov 26 - Nov 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Save 100% on your flight
Price was $863, price is now $490 per person
$490
per person
Dec 10 - Dec 15
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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $553, price is now $323 per person
$323
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,059, price is now $622 per person
$622
per person
Dec 23 - Dec 26
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.
Pendry Chicago
Save 100% on your flight
Price was $523, price is now $310 per person
$310
per person
Dec 18 - Dec 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, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Waldorf Astoria Chicago
Save 100% on your flight
Price was $1,306, price is now $788 per person
$788
per person
Dec 31 - Jan 3
found 24 hours ago
Roundtrip flight included
Dallas (DFW) 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.
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.
Fri, Oct 31 - Thu, Nov 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 14 hours ago
$110
Roundtrip
found 14 hours ago
Wed, Oct 29 - Mon, Nov 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Tue, Nov 4 - Thu, Dec 4
PVG
Pudong Intl.
ORD
O'Hare Intl.
$948 Roundtrip, found 2 days ago
$948
Roundtrip
found 2 days ago
Discover Other Travel Deals
- Lake Michigan Vacations
- Indiana Dunes National Park Vacations
- University of Chicago Vacations
- State Street Vacations
- Chicago Museum of Science and Industry Vacations
- Hard Rock Casino Northern Indiana Vacations
- Ameristar Casino East Chicago Vacations
- Credit Union 1 Amphitheatre Vacations
- Tinley Park Convention Center Vacations
- Purdue University Northwest Vacations
- Deep River Water Park Vacations
- Crown Point Sports Complex Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
