Search Deals onHighwood Vacation Packages
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Highwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $410, price is now $243 per person
$243
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $588, price is now $352 per person
$352
per person
Mar 2 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Arlo Chicago
Save 100% on your flight
Price was $515, price is now $335 per person
$335
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $905, price is now $594 per person
$594
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Virgin Hotels Chicago
Save 100% on your flight
Price was $550, price is now $363 per person
$363
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Emily Hotel
Price was $721, price is now $478 per person
$478
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Chicago Athletic Association, a Hyatt Hotel
Save 100% on your flight
Price was $545, price is now $366 per person
$366
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $408, price is now $275 per person
$275
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Highwood Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Highwood 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, Jan 17 - Sun, Jan 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Sat, Feb 14 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 19 hours ago
$163
Roundtrip
found 19 hours ago
Thu, Jan 8 - Thu, Jan 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$194 Roundtrip, found 6 hours ago
$194
Roundtrip
found 6 hours ago
Thu, May 14 - Sat, May 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,172 Roundtrip, found 4 hours ago
$1,172
Roundtrip
found 4 hours ago
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