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Hillside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was $1,127, price is now $462 per person
$462
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Art Villa

Art Villa

5 out of 5
Save 100% on your flight
Price was $1,900, price is now $958 per person
$958
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $773, price is now $403 per person
$403
per person
Dec 31 - Jan 4
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $694, price is now $364 per person
$364
per person
Dec 31 - Jan 4
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $739, price is now $410 per person
$410
per person
Jan 7 - Jan 10
found 19 hours 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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $993, price is now $610 per person
$610
per person
Dec 26 - Dec 29
found 14 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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,225, price is now $756 per person
$756
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hillside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $364 per person
$364
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,127, price is now $462 per person
$462
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $773, price is now $403 per person
$403
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $739, price is now $410 per person
$410
per person
Jan 7 - Jan 10
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Hillside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $931, price is now $472 per person
$472
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $996, price is now $491 per person
$491
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,900, price is now $958 per person
$958
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $78 found 1 day ago
Spirit Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $110 found 1 day ago
Frontier Airlines
Thu, Oct 23 - Sun, Oct 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Los Angeles Intl. to Midway Intl., returning Sun, Oct 26, priced at $219 found 4 days ago
All Nippon Airways
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 3 days ago
$999
Roundtrip
found 3 days ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $999 found 3 days ago