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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $450, price is now $301 per person
$301
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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 $698, price is now $395 per person
$395
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,418, price is now $831 per person
$831
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,130, price is now $686 per person
$686
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $770, price is now $492 per person
$492
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,345, price is now $862 per person
$862
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip 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 – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,051, price is now $698 per person
$698
per person
Dec 13 - Dec 20
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $662, price is now $448 per person
$448
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Hillsdale Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
Save 100% on your flight
Price was $383, price is now $250 per person
$250
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $827, price is now $465 per person
$465
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,061, price is now $604 per person
$604
per person
Dec 11 - Dec 14
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,345, price is now $862 per person
$862
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip 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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $552, price is now $297 per person
$297
per person
Dec 10 - Dec 15
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 $626, price is now $328 per person
$328
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $761, price is now $406 per person
$406
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,840, price is now $1,033 per person
$1,033
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Top Flight Deals

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

American Airlines
Wed, Nov 19 - Wed, Dec 3
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$191 Roundtrip, found 10 hours ago
$191
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Nov 19 from Austin-Bergstrom Intl. to Quad City Intl., returning Wed, Dec 3, priced at $191 found 10 hours ago
Bargain Flight
Tue, Oct 14 - Tue, Oct 21
SAN
San Diego Intl.
MLI
Quad City Intl.
$288 Roundtrip, found 3 hours ago
$288
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Tue, Oct 14 from San Diego Intl. to Quad City Intl., returning Tue, Oct 21, priced at $288 found 3 hours ago
United
Sat, Oct 11 - Wed, Oct 15
DEN
Denver Intl.
MLI
Quad City Intl.
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select United flight, departing Sat, Oct 11 from Denver Intl. to Quad City Intl., returning Wed, Oct 15, priced at $294 found 1 day ago
Delta
Mon, Dec 22 - Sun, Jan 4
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$399 Roundtrip, found 1 day ago
$399
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Dec 22 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Sun, Jan 4, priced at $399 found 1 day ago