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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.
Chicago Marriott Southwest at Burr Ridge

Chicago Marriott Southwest at Burr Ridge

4 out of 5
Save 100% on your flight
Price was $616, price is now $408 per person
$408
per person
Nov 12 - Nov 16
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Burr Ridge. Enjoy a 24-hour fitness center, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Burr Ridge Village Center and Flagg Creek Golf Course are located nearby.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $690, price is now $415 per person
$415
per person
Nov 6 - Nov 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, 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.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,086, price is now $687 per person
$687
per person
Nov 6 - Nov 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 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 Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
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.
It is the greatest will be there again

Reviewed on Sep 29, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $848, price is now $556 per person
$556
per person
Dec 2 - Dec 6
found 21 hours 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.
👍

Reviewed on Sep 28, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $908, price is now $611 per person
$611
per person
Nov 6 - Nov 9
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.
Amazing view, very clean room

Reviewed on Sep 30, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $776, price is now $532 per person
$532
per person
Nov 6 - 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 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

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $943, price is now $650 per person
$650
per person
Nov 20 - Nov 23
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.

Gary Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $698, price is now $418 per person
$418
per person
Nov 25 - Nov 28
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 $1,261, price is now $732 per person
$732
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $848, price is now $556 per person
$556
per person
Dec 2 - Dec 6
found 21 hours 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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $982, price is now $580 per person
$580
per person
Nov 19 - Nov 24
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,191, price is now $640 per person
$640
per person
Nov 19 - Nov 24
found 2 hours 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 $1,836, price is now $1,081 per person
$1,081
per person
Nov 19 - Nov 24
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,112, price is now $659 per person
$659
per person
Nov 19 - Nov 24
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Thu, Oct 29 - Tue, Nov 3
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Tue, Nov 3, priced at $188 found 2 days ago
Frontier Airlines
Mon, Oct 26 - Thu, Nov 5
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Detroit Metropolitan Wayne County to Midway Intl., returning Thu, Nov 5, priced at $190 found 3 days ago
American Airlines
Tue, Dec 8 - Wed, Dec 30
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 8 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Dec 30, priced at $197 found 1 day ago
Frontier Airlines
Fri, Dec 11 - Wed, Dec 30
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$323 Roundtrip, found 12 hours ago
$323
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Dec 11 from Southwest Florida Intl. to O'Hare Intl., returning Wed, Dec 30, priced at $323 found 12 hours ago