Worth Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Worth Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Price was $999, price is now $696 per person
$696
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this 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 Chicago Riverwalk and Millennium Park are located nearby.
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,874, price is now $1,132 per person
$1,132
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,927, price is now $1,240 per person
$1,240
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $783 per person
$783
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
Price was $1,081, price is now $715 per person
$715
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,034, price is now $739 per person
$739
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Top Hotel Deals
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
25.28 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
26.37 km from city center
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
27.3 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
24.89 km from city center
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 ...
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
25.95 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
25.98 km from city center
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 ...
River Hotel
75 East Wacker Drive Chicago IL
26 km from city center
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 Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
27.07 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
Hilton Chicago
720 S Michigan Ave Chicago IL
24.61 km from city center
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 ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
26.65 km from city center
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 ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
26.4 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
26.5 km from city center
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 ...
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand Chicago IL
27.34 km from city center
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 ...
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.
Wed, Dec 17 - Thu, Jan 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Thu, Dec 18 - Wed, Dec 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Wed, Dec 17 - Tue, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$347 Roundtrip, found 2 days ago
$347
Roundtrip
found 2 days ago
Sat, Jan 3 - Wed, Jan 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$452 Roundtrip, found 1 day ago
$452
Roundtrip
found 1 day ago
Sat, Jan 3 - Wed, Jan 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$471 Roundtrip, found 1 day ago
$471
Roundtrip
found 1 day ago