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Oswego Vacation Packages

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Oswego Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
per person
May 2 - May 4
found 24 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 3-star 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 Michigan Avenue and Chicago Riverwalk are located nearby.
The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
found 12 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and Kohl Children's Museum are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Staybridge Suites Chicago - Glenview by IHG

Staybridge Suites Chicago - Glenview by IHG

3 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
found 12 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star golf hotel in Glenview. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kohl Children's Museum and Glenview Prairie Golf Club are located nearby.
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
found 12 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Soldier Field and Chicago Museum of Science and Industry are located nearby.
Kinzie Hotel

Kinzie Hotel

4 out of 5
per person
Jun 13 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy a sauna, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Oswego Vacation Packages 3-4 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
Save 100% on your flight
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)

Oswego Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 7
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 3 - Jun 9
found 13 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

Top Flight Deals

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

Spirit Airlines
Thu, Apr 10 - Tue, Apr 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 6 days ago
$134
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Apr 10 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 15, priced at $134 found 6 days ago
United
Wed, Apr 23 - Tue, Apr 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select United flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 29, priced at $181 found 1 day ago
Delta
Sat, Apr 19 - Wed, Apr 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Apr 19 from Los Angeles Intl. to Midway Intl., returning Wed, Apr 23, priced at $257 found 1 day ago
Hong Kong Airlines
Sun, Jun 29 - Sun, Jul 27
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,170 Roundtrip, found 5 days ago
$1,170
Roundtrip
found 5 days ago
Select Hong Kong Airlines flight, departing Sun, Jun 29 from Hong Kong Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $1,170 found 5 days ago