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Hillsdale Vacation Packages

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Hillsdale Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $739, price is now $489 per person
$489
per person
Jul 18 - Jul 21
found 8 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,140, price is now $727 per person
$727
per person
Jul 1 - Jul 5
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $919, price is now $592 per person
$592
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,030, price is now $673 per person
$673
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,027, price is now $673 per person
$673
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park 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 $1,262, price is now $854 per person
$854
per person
Aug 13 - Aug 16
found 19 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.
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 $877, price is now $608 per person
$608
per person
Aug 5 - Aug 8
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.
Lodge Geneva National

Lodge Geneva National

4 out of 5
Save 100% on your flight
Price was $1,466, price is now $1,017 per person
$1,017
per person
Jul 2 - Jul 7
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Geneva National Golf Club are located nearby.

Hillsdale Vacation Packages 3-4 Night Stays

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $919, price is now $592 per person
$592
per person
Jul 1 - Jul 5
found 1 day 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 $1,140, price is now $727 per person
$727
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $673 per person
$673
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,027, price is now $673 per person
$673
per person
Aug 13 - Aug 16
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,400, price is now $874 per person
$874
per person
Aug 11 - Aug 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,177, price is now $1,210 per person
$1,210
per person
Jul 28 - Aug 2
found 1 day 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 $1,948, price is now $1,089 per person
$1,089
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,589, price is now $957 per person
$957
per person
Jul 16 - Jul 21
found 1 day 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.

American Airlines
Sat, Jul 4 - Sat, Jul 4
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$230 Roundtrip, found 15 hours ago
$230
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Sat, Jul 4 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Jul 4, priced at $230 found 15 hours ago
Delta
Sat, Jun 27 - Mon, Jun 29
DEN
Denver Intl.
MLI
Quad City Intl.
$289 Roundtrip, found 4 hours ago
$289
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Jun 27 from Denver Intl. to Quad City Intl., returning Mon, Jun 29, priced at $289 found 4 hours ago
Delta
Thu, Jul 2 - Fri, Jul 17
SEA
Seattle - Tacoma Intl.
MLI
Quad City Intl.
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jul 2 from Seattle - Tacoma Intl. to Quad City Intl., returning Fri, Jul 17, priced at $377 found 6 days ago
Delta
Fri, Sep 11 - Mon, Sep 14
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$399 Roundtrip, found 6 days ago
$399
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Mon, Sep 14, priced at $399 found 6 days ago