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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 $412, price is now $247 per person
$247
per person
May 11 - May 14
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,595, price is now $806 per person
$806
per person
May 28 - May 31
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $1,267, price is now $742 per person
$742
per person
May 28 - May 31
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $1,359, price is now $820 per person
$820
per person
May 28 - May 31
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $703, price is now $436 per person
$436
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
New Orleans (MSY) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
Price was $654, price is now $415 per person
$415
per person
May 19 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Chicago Ridge Shopping Mall and PGN Jump N' Fun Entertainment are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Price was $619, price is now $398 per person
$398
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $578, price is now $379 per person
$379
per person
May 11 - May 14
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.
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 $412, price is now $247 per person
$247
per person
May 11 - May 14
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 $1,595, price is now $806 per person
$806
per person
May 28 - May 31
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
Price was $1,267, price is now $742 per person
$742
per person
May 28 - May 31
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 $1,359, price is now $820 per person
$820
per person
May 28 - May 31
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,354, price is now $684 per person
$684
per person
May 20 - May 25
found 9 hours 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 $1,200, price is now $697 per person
$697
per person
May 20 - May 25
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,181, price is now $690 per person
$690
per person
May 20 - May 25
found 9 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 $1,548, price is now $916 per person
$916
per person
May 21 - May 26
found 2 hours ago
Roundtrip flight included
Portland (PDX) 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, Apr 23 - Sat, May 9
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$85 Roundtrip, found 23 hours ago
$85
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Southwest Florida Intl. to O'Hare Intl., returning Sat, May 9, priced at $85 found 23 hours ago
Spirit Airlines
Wed, Apr 29 - Tue, May 12
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Apr 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Tue, May 12, priced at $137 found 2 days ago
Frontier Airlines
Wed, Mar 18 - Tue, Mar 24
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$175 Roundtrip, found 6 hours ago
$175
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Mar 18 from Detroit Metropolitan Wayne County to Midway Intl., returning Tue, Mar 24, priced at $175 found 6 hours ago
Delta
Sat, May 2 - Sat, May 2
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, May 2 from Southwest Florida Intl. to Midway Intl., returning Sat, May 2, priced at $213 found 3 days ago