
Waterman Vacations
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Waterman Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Chicago Club Inn & Suites
Price was $616, price is now $538 per person
$538
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Ty Warner Park are located nearby.

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was $847, price is now $704 per person
$704
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Overall my stay was pretty good. The only two issues were my mini fridge wasn’t working and I lost my leftovers that sat in there for the two days I stayed. Secondly, I had a staff member tell me about a special tour and promotion, only to tell me somehow I was not eligible. Then he had me bring my son down to see if he could be eligible. He was only 18,not 21. So he was not. That was not very pleasant considering it was basically pulled back for some reason . I visit 3-4 times a year. I either stay at the Westin River north or the Royal Sonesta River North. The lost food was no biggie but being given a whole rundown about how the hotel was trying to build a new customer base and then being told I wasn’t eligible was crappy. I can’t lie. Everything else was pretty good. The happy hours were cool. Staff outside of that was generally ok.
Reviewed on Nov 2, 2026

Omni Chicago Hotel
Downtown Chicago
Price was $955, price is now $816 per person
$816
per person
Dec 3 - Dec 7
found 18 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Located in the heart of the city. Staff is always friendly and helpful
Reviewed on Nov 2, 2026

Comfort Inn & Suites Geneva - West Chicago
Price was $678, price is now $581 per person
$581
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions American Science & Surplus Store and Fabyan Windmill are located nearby.
The hotel was immaculate and the staff was very nice and helpful.
Reviewed on Nov 2, 2026

LIVN - West Loop Chicago
Downtown Chicago
Price was $942, price is now $819 per person
$819
per person
Dec 3 - Dec 7
found 18 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and laundry facilities. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Great experience would recommend to anyone who’s trying to stay in the city for the weekend
Reviewed on Nov 3, 2026

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
Price was $876, price is now $771 per person
$771
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Wel located hotel. Clean. Helpful staff. Too bad they don't offer breakfast.
Reviewed on Nov 1, 2026
Top Hotel Deals

Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
22.66 km from city center
Book a stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...

Holiday Inn Express & Suites Yorkville by IHG
577 E KENDALL DRIVE Yorkville IL
29.86 km from city center
Book a stay at this spa hotel in Yorkville. Enjoy free breakfast, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road Sycamore IL
24.08 km from city center
Book a stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
17.27 km from city center
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...

Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
28.97 km from city center
Stay at this motel in Rochelle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...

The Montcler Hotel - Redberri Luxury Collection
3300 Drew Ave Sandwich IL
21.14 km from city center
Book a stay at this business-friendly hotel in Sandwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Farnsworth House and Silver Springs ...

Best Western Rochelle Inn & Suites near DeKalb
1133 N. 7th St., Hwy 251 and Rt, 38 Rochelle IL
30.59 km from city center
Book a stay at this business-friendly hotel in Rochelle. Enjoy free parking, a 24-hour front desk, and a 24-hour business center. Our guests praise the helpful ...

Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
17.44 km from city center
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...

Super 8 by Wyndham Yorkville
1510 A North Bridge St Yorkville IL
30.12 km from city center
Book a stay at this business-friendly motel in Yorkville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...

Motel 6 Sycamore, IL
1860 Dekalb Ave Sycamore IL
22.91 km from city center
Stay at this motel in Sycamore. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...

Comfort Inn DeKalb - University Area
W Lincoln Hwy, 1314,1314 DeKalb IL
18.07 km from city center
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Huskie Stadium and NIU Convocation ...

Holiday Inn Express Rochelle by IHG
1240 North Dement Road Rochelle IL
28.61 km from city center
Book a stay at this business-friendly hotel in Rochelle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Super 8 by Wyndham DeKalb IL
800 W Fairview Dr DeKalb IL
15.49 km from city center
Book a stay at this business-friendly motel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Popular attractions River Heights Golf Course and Huskie ...
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.

