Highwood Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Highwood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$555
per person
Dec 8 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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 Riu Plaza Chicago
Downtown Chicago
$725
per person
Dec 8 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Great place to stay
Reviewed on Sep 19, 2026
The Talbott, Autograph Collection
Downtown Chicago
$767
per person
Dec 8 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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 helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
$819
per person
Dec 8 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$640
per person
Dec 8 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Clean room
Reviewed on Sep 19, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
$809
per person
Dec 8 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Top Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
Loews Chicago O'Hare Hotel
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
5460 North River Road Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff ...
Embassy Suites by Hilton Chicago O'Hare Rosemont
5500 N River Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and ...
DoubleTree by Hilton Chicago - North Shore Conference Center
9599 Skokie Blvd Skokie IL
Book a stay at this business-friendly hotel in Skokie. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn Chicago North-Evanston by IHG
1501 Sherman Ave Evanston IL
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Sheraton Suites Chicago O'Hare
6501 N Mannheim Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful ...
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Quality Inn O'Hare Airport
3801 North Mannheim Road Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff ...
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, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$156
Roundtrip
found 3 days ago
Wed, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$186
Roundtrip
found 3 days ago
Wed, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$215
Roundtrip
found 3 days ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216
Roundtrip
found 3 days ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 3 days ago
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