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Gary Vacation Packages

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Gary 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 $486, price is now $239 per person
$239
per person
Feb 12 - Feb 15
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.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was $1,128, price is now $467 per person
$467
per person
Dec 22 - Dec 26
found 24 hours 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 a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $858, price is now $463 per person
$463
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $463, price is now $254 per person
$254
per person
Feb 12 - Feb 15
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $626, price is now $354 per person
$354
per person
Feb 12 - Feb 15
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 $922, price is now $523 per person
$523
per person
Feb 12 - Feb 15
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 French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Price was $552, price is now $316 per person
$316
per person
Dec 31 - Jan 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Geneva National Golf Club and Lake Como are located nearby.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $651, price is now $376 per person
$376
per person
Jan 21 - Jan 25
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.

Gary 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 $486, price is now $239 per person
$239
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,128, price is now $467 per person
$467
per person
Dec 22 - Dec 26
found 24 hours 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 $858, price is now $463 per person
$463
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $463, price is now $254 per person
$254
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Gary Vacation Packages 5-7 Night Stays

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $898, price is now $440 per person
$440
per person
Feb 6 - Feb 13
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,403, price is now $486 per person
$486
per person
Dec 23 - Dec 28
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $1,385, price is now $536 per person
$536
per person
Feb 6 - Feb 13
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,356, price is now $700 per person
$700
per person
Feb 6 - Feb 13
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Top Flight Deals

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

Spirit Airlines
Wed, Dec 10 - Thu, Dec 11
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Dec 10 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Dec 11, priced at $147 found 5 days ago
Delta
Mon, Nov 24 - Sat, Dec 6
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$175 Roundtrip, found 5 days ago
$175
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 24 from Detroit Metropolitan Wayne County to Midway Intl., returning Sat, Dec 6, priced at $175 found 5 days ago
Spirit Airlines
Tue, Nov 25 - Tue, Dec 2
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Nov 25 from Southwest Florida Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $181 found 3 days ago
Delta
Wed, Dec 24 - Thu, Jan 1
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$277 Roundtrip, found 6 days ago
$277
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 24 from Southwest Florida Intl. to Midway Intl., returning Thu, Jan 1, priced at $277 found 6 days ago