Bellwood Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Bellwood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$539
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$671
per person
Dec 15 - Dec 21
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.
Swissotel - Chicago
Downtown Chicago
$798
per person
Dec 15 - Dec 21
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.
Great service
Reviewed on Oct 13, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$540
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel 505 River North
Downtown Chicago
$560
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$816
per person
Dec 15 - Dec 21
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 WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
I really enjoyed my stay at the Sable Hotel in Chicago. I happened to be visiting during the Chicago Marathon, so finding a hotel wasn't easy. I ended up booking the Sable, and I'm glad I did. The hotel is beautiful, the rooms are clean, modern, and comfortable, and the views of Lake Michigan and the city from Navy Pier are hard to beat.
I was genuinely impressed with how nice the property was. Everything was well-maintained, and I really enjoyed the location. What started as a scramble to find a room turned out to be a great experience. I'd absolutely stay here again and would recommend it to anyone visiting Chicago.
Reviewed on Oct 13, 2026
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
The Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
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 ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Freehand Chicago
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Hotel Saint Clair- Magnificent Mile
162 East Ontario Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Sports Illustrated Resorts Chicago
203 N Wabash Ave Chicago IL
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 ...
The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177
Roundtrip
found 5 days ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177
Roundtrip
found 5 days ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177
Roundtrip
found 5 days ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$177
Roundtrip
found 6 days ago
Sat, Nov 14 - Mon, Nov 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200
Roundtrip
found 5 days ago
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