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Hillsdale Vacation Packages

Build your package with 2 more options

Hillsdale Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $268, price is now $167 per person
$167
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $635, price is now $351 per person
$351
per person
Jan 1 - Jan 4
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

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $587, price is now $350 per person
$350
per person
Jan 1 - 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $549, price is now $330 per person
$330
per person
Jan 16 - Jan 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $515, price is now $320 per person
$320
per person
Jan 1 - 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $378, price is now $235 per person
$235
per person
Jan 23 - Jan 25
found 7 hours 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.
Hotel Versey Chicago Lincoln Park

Hotel Versey Chicago Lincoln Park

3 out of 5
Save 100% on your flight
Price was $724, price is now $452 per person
$452
per person
Dec 22 - Dec 28
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $407, price is now $254 per person
$254
per person
Dec 7 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Hillsdale Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $587, price is now $350 per person
$350
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $351 per person
$351
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $580, price is now $352 per person
$352
per person
Jan 16 - Jan 19
found 23 hours ago
Roundtrip flight included
Baltimore (BWI) 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 $999, price is now $607 per person
$607
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Hillsdale Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $726, price is now $368 per person
$368
per person
Jan 16 - Jan 23
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,010, price is now $474 per person
$474
per person
Jan 16 - Jan 23
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $746, price is now $368 per person
$368
per person
Jan 16 - Jan 23
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $796, price is now $404 per person
$404
per person
Jan 16 - Jan 23
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

United
Tue, Dec 16 - Tue, Jan 6
DEN
Denver Intl.
MLI
Quad City Intl.
$222 Roundtrip, found 13 hours ago
$222
Roundtrip
found 13 hours ago
Select United flight, departing Tue, Dec 16 from Denver Intl. to Quad City Intl., returning Tue, Jan 6, priced at $222 found 13 hours ago
American Airlines
Wed, Dec 17 - Mon, Jan 5
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$223 Roundtrip, found 6 days ago
$223
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Dec 17 from Austin-Bergstrom Intl. to Quad City Intl., returning Mon, Jan 5, priced at $223 found 6 days ago
Bargain Flight
Thu, Nov 27 - Wed, Dec 3
SAN
San Diego Intl.
MLI
Quad City Intl.
$266 Roundtrip, found 14 hours ago
$266
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Thu, Nov 27 from San Diego Intl. to Quad City Intl., returning Wed, Dec 3, priced at $266 found 14 hours ago
American Airlines
Wed, Dec 17 - Mon, Dec 22
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$399 Roundtrip, found 2 hours ago
$399
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Dec 17 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Mon, Dec 22, priced at $399 found 2 hours ago