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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.
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $352, price is now $229 per person
$229
per person
Feb 2 - Feb 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 WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $503, price is now $303 per person
$303
per person
Mar 5 - Mar 8
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, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $623, price is now $377 per person
$377
per person
Mar 5 - Mar 8
found 1 day 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $597, price is now $362 per person
$362
per person
Feb 20 - Feb 22
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $578, price is now $353 per person
$353
per person
Mar 5 - Mar 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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $622, price is now $381 per person
$381
per person
Mar 5 - Mar 8
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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
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 $552, price is now $355 per person
$355
per person
Mar 5 - Mar 8
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 $577, price is now $371 per person
$371
per person
Mar 5 - Mar 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 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $503, price is now $303 per person
$303
per person
Mar 5 - Mar 8
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 $830, price is now $477 per person
$477
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $623, price is now $377 per person
$377
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $578, price is now $353 per person
$353
per person
Mar 5 - Mar 8
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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $717, price is now $436 per person
$436
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $982, price is now $572 per person
$572
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $1,420, price is now $832 per person
$832
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $1,077, price is now $633 per person
$633
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop 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.

United
Wed, Dec 24 - Wed, Jan 7
DEN
Denver Intl.
MLI
Quad City Intl.
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select United flight, departing Wed, Dec 24 from Denver Intl. to Quad City Intl., returning Wed, Jan 7, priced at $274 found 1 day ago
United
Wed, Dec 24 - Wed, Jan 7
DEN
Denver Intl.
MLI
Quad City Intl.
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day ago
Select United flight, departing Wed, Dec 24 from Denver Intl. to Quad City Intl., returning Wed, Jan 7, priced at $276 found 1 day ago
Delta
Wed, Dec 24 - Tue, Jan 6
DEN
Denver Intl.
MLI
Quad City Intl.
$284 Roundtrip, found 1 day ago
$284
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 24 from Denver Intl. to Quad City Intl., returning Tue, Jan 6, priced at $284 found 1 day ago
Delta
Tue, Dec 30 - Thu, Jan 8
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$419 Roundtrip, found 4 days ago
$419
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Dec 30 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Thu, Jan 8, priced at $419 found 4 days ago