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 Fulton Market
Save 100% on your flight
Price was $1,556, price is now $815 per person
$815
per person
Oct 28 - Nov 3
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 a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Great! But parking was bad.
Reviewed on Aug 26, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,790, price is now $1,044 per person
$1,044
per person
Oct 27 - 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.
The Emily Hotel
Save 100% on your flight
Price was $1,901, price is now $1,241 per person
$1,241
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 $1,204, price is now $799 per person
$799
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.
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $1,225, price is now $820 per person
$820
per person
Nov 11 - Nov 15
found 6 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $2,868, price is now $1,924 per person
$1,924
per person
Oct 27 - 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 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.
Level Chicago - River North
Save 100% on your flight
Price was $1,819, price is now $1,273 per person
$1,273
per person
Oct 27 - Nov 3
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 a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I would like to come back it’s safe and clean u can see the view
Reviewed on Aug 26, 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 14 hours ago
$181
Roundtrip
found 14 hours ago
Mon, Oct 5 - Mon, Oct 19
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Thu, Oct 1 - Mon, Oct 5
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$287 Roundtrip, found 14 hours ago
$287
Roundtrip
found 14 hours ago
Fri, Aug 28 - Tue, Sep 1
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$298 Roundtrip, found 14 hours ago
$298
Roundtrip
found 14 hours ago
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