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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 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 $827, price is now $520 per person
$520
per person
Aug 8 - Aug 11
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,103, price is now $672 per person
$672
per person
Jul 24 - Jul 27
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 $917, price is now $565 per person
$565
per person
Jul 24 - Jul 27
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.
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 $1,056, price is now $685 per person
$685
per person
Jul 24 - Jul 27
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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $958, price is now $623 per person
$623
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,987, price is now $1,295 per person
$1,295
per person
Jul 31 - Aug 4
found 1 day 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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,681, price is now $1,099 per person
$1,099
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $877, price is now $582 per person
$582
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.

Hillsdale Vacation Packages 3-4 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
Save 100% on your flight
Price was $827, price is now $520 per person
$520
per person
Aug 8 - Aug 11
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 $1,103, price is now $672 per person
$672
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $917, price is now $565 per person
$565
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,056, price is now $685 per person
$685
per person
Jul 24 - Jul 27
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,349, price is now $734 per person
$734
per person
Jul 23 - Jul 28
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 $1,525, price is now $849 per person
$849
per person
Jul 23 - Jul 28
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 $1,533, price is now $908 per person
$908
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,220, price is now $762 per person
$762
per person
Jun 24 - Jun 30
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 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 1 day ago
$377
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jul 2 from Seattle - Tacoma Intl. to Quad City Intl., returning Fri, Jul 17, priced at $377 found 1 day ago