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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $685, price is now $482 per person
$482
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). 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

Level Chicago Fulton Market

4 out of 5
Price was $910, price is now $574 per person
$574
per person
Jan 23 - Jan 27
found 9 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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $725, price is now $486 per person
$486
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Price to high for the quality.

Reviewed on Nov 9, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $815, price is now $555 per person
$555
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Great location. Hotel just ok. Having a bar/restaurant below, was a convenience. However, you basically had to doordash to get them to deliver to your room... inconvenience. For the location, alone, I'd stay here again.

Reviewed on Nov 9, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
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.
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $1,054, price is now $754 per person
$754
per person
Jan 22 - Jan 25
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.
Great

Reviewed on Nov 9, 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $1,051, price is now $764 per person
$764
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 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
Price was $2,050, price is now $1,501 per person
$1,501
per person
Dec 23 - Dec 29
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.
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨

Reviewed on Nov 9, 2026

Gary Vacation Packages 3-4 Night Stays

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
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
Price was $910, price is now $574 per person
$574
per person
Jan 23 - Jan 27
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $725, price is now $486 per person
$486
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $815, price is now $555 per person
$555
per person
Jan 22 - Jan 25
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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was $713, price is now $453 per person
$453
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $806, price is now $491 per person
$491
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,305, price is now $815 per person
$815
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,390, price is now $871 per person
$871
per person
Dec 24 - Dec 31
found 5 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, Dec 10 - Mon, Dec 14
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Dec 10 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Dec 14, priced at $193 found 4 days ago
Delta
Tue, Dec 1 - Sat, Dec 5
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 1 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Sat, Dec 5, priced at $219 found 2 days ago
Frontier Airlines
Tue, Nov 24 - Wed, Nov 25
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$260 Roundtrip, found 2 hours ago
$260
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Detroit Metropolitan Wayne County to Midway Intl., returning Wed, Nov 25, priced at $260 found 2 hours ago
Southwest Airlines
Thu, Dec 10 - Mon, Dec 14
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Southwest Florida Intl. to Midway Intl., returning Mon, Dec 14, priced at $319 found 4 days ago