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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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Price was $810, price is now $589 per person
$589
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,447, price is now $1,000 per person
$1,000
per person
Jul 2 - Jul 5
found 17 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Lodge Geneva National

Lodge Geneva National

4 out of 5
Save 100% on your flight
Price was $2,284, price is now $1,590 per person
$1,590
per person
Jul 9 - Jul 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,397, price is now $981 per person
$981
per person
Jun 26 - Jun 29
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,919, price is now $1,366 per person
$1,366
per person
Jul 2 - Jul 5
found 17 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,752, price is now $1,259 per person
$1,259
per person
Jul 9 - Jul 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions The Highlands Golf Course and The Brute Golf Course are located nearby.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $836, price is now $605 per person
$605
per person
Jul 14 - Jul 20
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,072, price is now $788 per person
$788
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip flight included
Columbus (CMH) 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.

Hillsdale Vacation Packages 3-4 Night Stays

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

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $953, price is now $660 per person
$660
per person
Aug 14 - Aug 17
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,464, price is now $1,009 per person
$1,009
per person
Jul 2 - Jul 5
found 18 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,447, price is now $1,000 per person
$1,000
per person
Jul 2 - Jul 5
found 17 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,397, price is now $981 per person
$981
per person
Jun 26 - Jun 29
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)

Hillsdale Vacation Packages 5-7 Night Stays

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

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,113, price is now $738 per person
$738
per person
Jul 16 - Jul 21
found 17 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,429, price is now $905 per person
$905
per person
Jul 1 - Jul 6
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,148, price is now $745 per person
$745
per person
Jul 1 - Jul 6
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,096, price is now $1,433 per person
$1,433
per person
Aug 9 - Aug 16
found 2 hours ago
Roundtrip flight included
Columbus (CMH) 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 6 days ago
$230
Roundtrip
found 6 days 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 6 days ago
American Airlines
Sat, Jul 11 - Mon, Jul 20
DEN
Denver Intl.
MLI
Quad City Intl.
$296 Roundtrip, found 5 days ago
$296
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jul 11 from Denver Intl. to Quad City Intl., returning Mon, Jul 20, priced at $296 found 5 days ago
Bargain Flight
Thu, May 28 - Tue, Jun 2
LAX
Los Angeles Intl.
MLI
Quad City Intl.
$305 Roundtrip, found 5 days ago
$305
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Thu, May 28 from Los Angeles Intl. to Quad City Intl., returning Tue, Jun 2, priced at $305 found 5 days ago
Delta
Thu, Jul 2 - Fri, Jul 17
SEA
Seattle - Tacoma Intl.
MLI
Quad City Intl.
$377 Roundtrip, found 2 days ago
$377
Roundtrip
found 2 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 2 days ago