Search Deals onGary Vacation Packages
Gary Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile
Save 100% on your flight
Price was $1,006, price is now $702 per person
$702
per person
Nov 5 - Nov 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 room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,539, price is now $821 per person
$821
per person
Oct 28 - Nov 3
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,827, price is now $1,055 per person
$1,055
per person
Oct 28 - Nov 3
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, 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.
Kinzie Hotel
Save 100% on your flight
Price was $1,373, price is now $882 per person
$882
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Emily Hotel
Save 100% on your flight
Price was $1,903, price is now $1,243 per person
$1,243
per person
Oct 27 - Nov 3
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.
Thompson Chicago, by Hyatt
Save 100% on your flight
Price was $1,209, price is now $801 per person
$801
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Silversmith Hotel Chicago Downtown
Save 100% on your flight
Price was $1,170, price is now $780 per person
$780
per person
Oct 28 - Nov 3
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 Millennium Park and Chicago Riverwalk are located nearby.
Thoroughly enjoyed our stay at the Silver Smith hotel. Its within walking distance of many sights. Plenty of food options available around the hotel as well.
Reviewed on Aug 26, 2026
The Peninsula Chicago
Save 100% on your flight
Price was $2,835, price is now $1,911 per person
$1,911
per person
Oct 28 - Nov 3
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 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
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.
Mon, Oct 19 - Fri, Oct 23
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$181 Roundtrip, found 2 hours ago
$181
Roundtrip
found 2 hours ago
Fri, Oct 16 - Tue, Oct 27
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$188 Roundtrip, found 6 days ago
$188
Roundtrip
found 6 days ago
Thu, Oct 1 - Mon, Oct 5
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$287 Roundtrip, found 2 hours ago
$287
Roundtrip
found 2 hours ago
Fri, Aug 28 - Tue, Sep 1
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$298 Roundtrip, found 2 hours ago
$298
Roundtrip
found 2 hours ago
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