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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $626, price is now $395 per person
$395
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
GreatGreat quite wonderful

Reviewed on Jul 30, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $881, price is now $503 per person
$503
per person
Oct 4 - Oct 7
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.
I had an amazing experience. The room was very clean with a comfy bed. The staff, especially Alan, was very helpful. He was patient and supportive.

Reviewed on Jul 30, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,125, price is now $734 per person
$734
per person
Oct 4 - Oct 7
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 property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.

Reviewed on Jul 28, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $748, price is now $493 per person
$493
per person
Oct 4 - Oct 7
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.
Nice location.

Reviewed on Jul 31, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,149, price is now $777 per person
$777
per person
Oct 15 - Oct 19
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.
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $701, price is now $474 per person
$474
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,017, price is now $689 per person
$689
per person
Oct 4 - Oct 7
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.
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $635, price is now $439 per person
$439
per person
Oct 4 - Oct 7
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.

Gary Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $626, price is now $395 per person
$395
per person
Oct 4 - Oct 7
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
Save 100% on your flight
Price was $881, price is now $503 per person
$503
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,125, price is now $734 per person
$734
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,257, price is now $826 per person
$826
per person
Sep 14 - Sep 17
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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $974, price is now $564 per person
$564
per person
Sep 30 - Oct 5
found 15 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 $1,711, price is now $953 per person
$953
per person
Sep 23 - Sep 28
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 $1,634, price is now $921 per person
$921
per person
Sep 30 - Oct 5
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,634, price is now $2,689 per person
$2,689
per person
Sep 13 - Sep 19
found 1 day 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
Tue, Sep 22 - Thu, Oct 8
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Detroit Metropolitan Wayne County to Midway Intl., returning Thu, Oct 8, priced at $180 found 7 hours ago
Frontier Airlines
Tue, Aug 18 - Wed, Aug 19
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Aug 19, priced at $237 found 22 hours ago
Bargain Flight
Tue, Sep 8 - Mon, Sep 14
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Sep 8 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Sep 14, priced at $263 found 1 day ago
Delta
Sat, Sep 5 - Wed, Sep 16
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$307 Roundtrip, found 3 days ago
$307
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 5 from Southwest Florida Intl. to Midway Intl., returning Wed, Sep 16, priced at $307 found 3 days ago