Afton Vacations
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Afton Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection
Downtown Chicago
Price was $968, price is now $765 per person
$765
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 Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,375, price is now $939 per person
$939
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 Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Price to high for the quality.
Reviewed on Nov 9, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,222, price is now $893 per person
$893
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,942, price is now $1,430 per person
$1,430
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this luxury 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 Chicago Riverwalk and Michigan Avenue are located nearby.
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨
Reviewed on Nov 9, 2026
Swissotel - Chicago
Downtown Chicago
Price was $1,165, price is now $882 per person
$882
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury 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.
Park Hyatt Chicago
Downtown Chicago
Price was $1,972, price is now $1,547 per person
$1,547
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
Baymont by Wyndham Janesville
616 Midland Rd Janesville WI
10.73 km from city center
Book a stay at this business-friendly hotel in Janesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
AmericInn by Wyndham Beloit
2790 Milwaukee Rd Beloit WI
11.5 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Microtel Inn by Wyndham Janesville
3121 Wellington Pl Janesville WI
14.38 km from city center
Book a stay at this business-friendly hotel in Janesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Motel 6 Janesville, WI
3907 Milton Ave Janesville WI
15.33 km from city center
Stay at this motel in Janesville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
AmericInn by Wyndham Janesville
3900 Milton Ave Janesville WI
15.27 km from city center
Book a stay at this business-friendly hotel in Janesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
Holiday Inn Express & Suites Beloit by IHG
3022 Ford Street Beloit WI
11.74 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Ironworks Hotel
500 Pleasant Street Rock Beloit WI
11.88 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Best Western Legacy Inn & Suites Beloit/South Beloit
5910 Technology Drive South Beloit IL
13.91 km from city center
Book a stay at this business-friendly hotel in South Beloit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Tru By Hilton Janesville
2702 Pontiac Place Janesville WI
14.31 km from city center
Stay at this hotel in Janesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hampton Inn Beloit
2700 Cranston Rd Beloit WI
11.44 km from city center
Stay at this hotel in Beloit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Fairfield Inn & Suites by Marriott Beloit
2784 Milwaukee Rd Beloit WI
11.42 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Turtle Creek Parkway and Leeson ...
Quality Inn Edgerton - Lake Koshkonong
11102 N Goede Rd Edgerton WI
25.98 km from city center
Book a stay at this business-friendly hotel in Edgerton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hotel Goodwin
500 Public Ave Beloit WI
11.93 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free WiFi, free parking, and room service. Popular attractions Bunge Studio Theatre and Kresge Experimental ...
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.