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Exclusive Kathy Osterman Beach Vacation Deals
Kathy Osterman Beach vacation package deals
Price found within the past 48 hours. Click for updated prices.
![Harrah's Joliet Casino & Hotel](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/00c3877d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Harrah's Joliet Casino & Hotel
Save 100% on your flight
per person
Jul. 30 - Aug. 6
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (CHI)
Stay at this 3.5-star business-friendly hotel in Joliet. Enjoy free WiFi, 4 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harrah's Casino and Route 66 Raceway are located nearby.
![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Aug. 8 - Aug. 12
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
![Ambassador Chicago, part of JdV by Hyatt](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/929cf7ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Ambassador Chicago, part of JdV by Hyatt
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 Michigan Avenue and Chicago Riverwalk are located nearby.
![Millennium Knickerbocker Chicago](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/cf5ebf5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Millennium Knickerbocker Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/425695dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 26 - Jul. 29
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/3226e31b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this spa 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Frequently asked questions
Top Kathy Osterman Beach hotel deals
![House 5863 - Chicago Bed and Breakfast](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/e7b04404_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
House 5863 - Chicago Bed and Breakfast
5863 North Glenwood Avenue, Chicago, IL
The price is CA $223 per night
CA $223
per night
Jul. 10 - Jul. 11
Stay at this 3.5-star business-friendly B&B in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Lincoln Park Zoo are located nearby.
Breakfast included
Parking included
![Heart O' Chicago](https://images.trvl-media.com/lodging/2000000/1670000/1669700/1669633/386468b4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Heart O' Chicago
5990 North Ridge Ave, Chicago, IL
The price is CA $184 per night
CA $184
per night
Jun. 27 - Jun. 28
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the convenient parking and the clean rooms in our reviews. Popular attractions Wrigley Field and Lincoln Park Zoo are located nearby.
Parking included
Free WiFi
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View all propertiesLowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.