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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $750, price is now $427 per person
$427
per person
Mar 23 - Mar 28
found 16 hours 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $829, price is now $428 per person
$428
per person
Mar 23 - Mar 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,062, price is now $595 per person
$595
per person
Mar 23 - Mar 28
found 16 hours 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $963, price is now $545 per person
$545
per person
Mar 23 - Mar 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,594, price is now $925 per person
$925
per person
Mar 24 - Mar 29
found 15 hours 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $838, price is now $493 per person
$493
per person
Mar 23 - Mar 28
found 16 hours 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.
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 $974, price is now $580 per person
$580
per person
Mar 23 - Mar 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $707, price is now $434 per person
$434
per person
Mar 23 - Mar 28
found 16 hours 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.

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 $688, price is now $417 per person
$417
per person
Mar 13 - Mar 16
found 16 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 $782, price is now $445 per person
$445
per person
Mar 13 - Mar 16
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $799, price is now $462 per person
$462
per person
Mar 13 - Mar 16
found 16 hours 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 $816, price is now $473 per person
$473
per person
Mar 13 - Mar 16
found 16 hours 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $750, price is now $427 per person
$427
per person
Mar 23 - Mar 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $829, price is now $428 per person
$428
per person
Mar 23 - Mar 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,062, price is now $595 per person
$595
per person
Mar 23 - Mar 28
found 16 hours 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 $963, price is now $545 per person
$545
per person
Mar 23 - Mar 28
found 16 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
Wed, Feb 4 - Wed, Feb 11
DEN
Denver Intl.
MLI
Quad City Intl.
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Feb 4 from Denver Intl. to Quad City Intl., returning Wed, Feb 11, priced at $212 found 11 hours ago
Delta
Wed, Feb 4 - Wed, Feb 11
DEN
Denver Intl.
MLI
Quad City Intl.
$229 Roundtrip, found 11 hours ago
$229
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Feb 4 from Denver Intl. to Quad City Intl., returning Wed, Feb 11, priced at $229 found 11 hours ago
Bargain Flight
Sat, May 16 - Sat, May 23
LAX
Los Angeles Intl.
MLI
Quad City Intl.
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, May 16 from Los Angeles Intl. to Quad City Intl., returning Sat, May 23, priced at $279 found 1 day ago
Bargain Flight
Fri, Apr 3 - Sun, Apr 5
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$337 Roundtrip, found 12 hours ago
$337
Roundtrip
found 12 hours ago
Select Bargain Flight flight, departing Fri, Apr 3 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Sun, Apr 5, priced at $337 found 12 hours ago