Search Deals onGary Vacation Packages
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Gary Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Embassy Suites by Hilton Chicago Downtown River North
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Swissotel - Chicago
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this eco-certified 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.

Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip flight included
Austin (AUS) 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.

Nobu Hotel Chicago
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.

Arlo Chicago
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Fairmont Chicago at Millennium Park
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this spa 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 Millennium Park and Chicago Riverwalk are located nearby.

Level Chicago – Old Town
Save 100% on your flight
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hilton Chicago/Magnificent Mile Suites
Save 100% on your flight
per person
Jul 18 - Jul 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Gary Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Gary Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Thu, Jun 26 - Sun, Jun 29
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago

Tue, Jul 15 - Wed, Jul 23
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago

Mon, Jun 30 - Sat, Jul 5
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$182 Roundtrip, found 5 days ago
$182
Roundtrip
found 5 days ago

Thu, Sep 4 - Thu, Sep 11
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$224 Roundtrip, found 6 days ago
$224
Roundtrip
found 6 days ago
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