Waterman Vacations

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Waterman Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Chicago Riverwalk and Millennium Park are located nearby.

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Top Hotel Deals

Holiday Inn Express & Suites Yorkville by IHG

Holiday Inn Express & Suites Yorkville by IHG

2.5 out of 5
577 E KENDALL DRIVE, Yorkville, IL
29.87 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

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
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 Yorkville

Hampton Inn Yorkville

2.5 out of 5
310 East Countryside Parkway, Yorkville, IL
30.28 km from city center
Book a stay at this business-friendly hotel in Yorkville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hampton Inn DeKalb, IL

Hampton Inn DeKalb, IL

3 out of 5
663 S. Annie Glidden Road, DeKalb, IL
17.27 km from city center
Stay at this 3-star business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Montcler Hotel & Conference Center, Trademark by Wyndham

Montcler Hotel & Conference Center, Trademark by Wyndham

3 out of 5
3300 Drew Ave, Sandwich, IL
20.97 km from city center
Stay at this 3-star business-friendly hotel in Sandwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Farnsworth House and Silver Springs ...
Comfort Inn & Suites Rochelle - DeKalb

Comfort Inn & Suites Rochelle - DeKalb

2.5 out of 5
1133 N 7th St, Rochelle, IL
30.56 km from city center
Book a stay at this business-friendly hotel in Rochelle. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in ...
Quality Inn

Quality Inn

2.5 out of 5
567 E IL Route 38, Rochelle, IL
28.98 km from city center
Stay at this hotel in Rochelle. Enjoy free breakfast, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Super 8 by Wyndham Rochelle

Super 8 by Wyndham Rochelle

2 out of 5
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 ...
Best Western Sycamore Inn

Best Western Sycamore Inn

2.5 out of 5
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. ...
Home2 Suites by Hilton Dekalb

Home2 Suites by Hilton Dekalb

3 out of 5
575 S ANNIE GLIDDEN RD, DeKalb, IL
17.44 km from city center
Stay at this 3-star business-friendly hotel in DeKalb. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Quality Inn Sycamore - DeKalb

Quality Inn Sycamore - DeKalb

2.5 out of 5
1475 South Peace Rd, Sycamore, IL
23.98 km from city center
Book a stay at this spa hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Motel 6 Sycamore, IL

Motel 6 Sycamore, IL

2 out of 5
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 ...
Super 8 by Wyndham DeKalb IL

Super 8 by Wyndham DeKalb IL

2 out of 5
800 W Fairview Dr, Jct I-88 & Annie Glidden Rd- Exit 91, 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 ...
Holiday Inn Express Rochelle by IHG

Holiday Inn Express Rochelle by IHG

2.5 out of 5
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 ...
Red Roof Inn & Suites DeKalb

Red Roof Inn & Suites DeKalb

2.5 out of 5
1212 West Lincoln Highway, DeKalb, IL
18.1 km from city center
Book a stay at this business-friendly hotel in DeKalb. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
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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.