Exclusive Kathy Osterman Beach Vacation Deals

Kathy Osterman Beach vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $256, price is now $166 per person
$166
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-in are also on offer.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,234, price is now $685 per person
$685
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $512, price is now $301 per person
$301
per person
Feb 14 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $323, price is now $207 per person
$207
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $446, price is now $287 per person
$287
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Frequently asked questions

How much are vacation packages to Kathy Osterman Beach?
If you like the idea of hassle-free planning and impressive savings, our $166 Kathy Osterman Beach vacation package will be right up your street. With your hotel and flights sorted, organizing your getaway around this renowned attraction is easier than ever.
Where can I get the best vacation package deals for Kathy Osterman Beach?
With around 400 airlines and 1,000,000 hotels across the world, it's hard to top Travelocity. Browse our comprehensive range and create the perfect Kathy Osterman Beach package deal. Isn't it great when traveling is that easy?
Why should I purchase my Kathy Osterman Beach vacation package via Travelocity?
By booking your flights, hotel, activities and car rental altogether, you'll save big bucks as well as precious time. We have an expert team of customer service specialists available 24/7, and you'll know that you're always getting the best deal in town with our Price Match Guarantee. So, what's stopping you? Book the vacation of your dreams today and get packing!

Top Kathy Osterman Beach hotel deals

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 out of 5
5863 North Glenwood Avenue Chicago IL
$149 nightly
The price is $174 total per night
$174 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the express check-out and free internet in public areas. A terrace, a garden, and a snack bar/deli are also on offer.
Breakfast included
Free WiFi
Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago

Chicago IL
$120 nightly
The price is $148 total per night
$148 total
Dec 15 - Dec 16
Total with taxes and fees
This apartment features laundry facilities.
Washer
Dryer
Luxurious 3 Bedroom Apartment in Chicago

Luxurious 3 Bedroom Apartment in Chicago

Chicago IL
This apartment features laundry facilities.
Washer
Dryer
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Lowest 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.