Search Deals onHighwood Vacation Packages
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Highwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Save 100% on your flight
Price was $493, price is now $261 per person
$261
per person
Jan 9 - Jan 12
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Price was $774, price is now $356 per person
$356
per person
Jan 16 - Jan 23
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.
Pendry Chicago
Price was $1,015, price is now $479 per person
$479
per person
Jan 16 - Jan 23
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.
theWit Chicago, a Hilton Hotel
Save 100% on your flight
Price was $719, price is now $372 per person
$372
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.
The Blackstone, Autograph Collection
Save 100% on your flight
Price was $705, price is now $370 per person
$370
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Price was $767, price is now $422 per person
$422
per person
Jan 9 - Jan 12
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $734, price is now $404 per person
$404
per person
Jan 16 - Jan 23
found 1 day 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.
Arlo Chicago
Save 100% on your flight
Price was $707, price is now $401 per person
$401
per person
Jan 16 - Jan 23
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.
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.
Thu, Nov 27 - Tue, Dec 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Tue, Dec 2 - Sat, Dec 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Thu, Dec 4 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
MDW
Midway Intl.
$736 Roundtrip, found 5 days ago
$736
Roundtrip
found 5 days ago
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