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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.
![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/2a95e836_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Willis Tower and Chicago Riverwalk are located nearby.
![Fairmont Chicago at Millennium Park Gold Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577141/223eec73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Millennium Park 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
Aug. 22 - Aug. 25
found 24 hours ago
Roundtrip flight included
Toronto (YTO) 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.
![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/0a75f592_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 22 - Aug. 25
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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. 11
found 22 hours ago
Roundtrip flight included
Toronto (YTO) 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.
![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/387b811c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Willis Tower 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 $237 per night
CA $237
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.
![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 $185 per night
CA $185
per night
Jun. 19 - Jun. 20
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.
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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.