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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.
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
Save 100% on your flight
Price was $853, price is now $558 per person
$558
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Yorktown Shopping Center and Mayslake Peabody Mansion are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $2,047, price is now $1,127 per person
$1,127
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,307, price is now $1,298 per person
$1,298
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,607, price is now $1,623 per person
$1,623
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
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 $2,537, price is now $1,581 per person
$1,581
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,930, price is now $1,257 per person
$1,257
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Save 100% on your flight
Price was $1,352, price is now $904 per person
$904
per person
Jul 29 - Aug 4
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Allstate Arena and Milwaukee Avenue are located nearby.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,712, price is now $1,147 per person
$1,147
per person
Jul 29 - Aug 2
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

Hillsdale Vacation Packages 3-4 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 $1,094, price is now $723 per person
$723
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,428, price is now $908 per person
$908
per person
Aug 2 - Aug 6
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,097, price is now $724 per person
$724
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,712, price is now $1,147 per person
$1,147
per person
Jul 29 - Aug 2
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,307, price is now $787 per person
$787
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,047, price is now $1,127 per person
$1,127
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,307, price is now $1,298 per person
$1,298
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,303, price is now $811 per person
$811
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Top Flight Deals

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

Delta
Sat, Jul 4 - Wed, Jul 15
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$236 Roundtrip, found 3 days ago
$236
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jul 4 from Austin-Bergstrom Intl. to Quad City Intl., returning Wed, Jul 15, priced at $236 found 3 days ago
Bargain Flight
Wed, May 27 - Tue, Jun 9
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, May 27 from Austin-Bergstrom Intl. to Quad City Intl., returning Tue, Jun 9, priced at $257 found 2 days ago
Delta
Thu, Jul 2 - Fri, Jul 17
SEA
Seattle - Tacoma Intl.
MLI
Quad City Intl.
$377 Roundtrip, found 4 days ago
$377
Roundtrip
found 4 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 4 days ago
Delta
Fri, Sep 11 - Mon, Sep 14
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$399 Roundtrip, found 4 days ago
$399
Roundtrip
found 4 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 4 days ago