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
Price was $820, price is now $643 per person
$643
per person
Dec 31 - Jan 5
found 5 hours 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 Riu Plaza Chicago
Downtown Chicago
Price was $1,309, price is now $869 per person
$869
per person
Dec 31 - Jan 5
found 5 hours 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.
The hotel is beautiful and the staff are attentive, friendly and welcoming. The hotel and our accommodations were very neat and clean. The hotel is in a great location downtown within walking distance of many attractions, shops, and restaurants. Highly recommend this hotel for anyone looking for a place to stay in downtown Chicago.
Reviewed on Nov 8, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,182, price is now $842 per person
$842
per person
Dec 31 - Jan 5
found 5 hours 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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $1,054 per person
$1,054
per person
Dec 21 - Dec 29
found 7 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 Blackstone, Autograph Collection
Downtown Chicago
Price was $1,237, price is now $921 per person
$921
per person
Dec 21 - Dec 29
found 7 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Nice property but a little worn.mattresses were not that comfortable .Some staff were great, others not so much.
Reviewed on Nov 8, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,274, price is now $1,001 per person
$1,001
per person
Dec 21 - Dec 29
found 7 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Top Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
26.57 km from city center
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 ...
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
24.73 km from city center
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 ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
25.4 km from city center
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 ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
25.85 km from city center
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
23.8 km from city center
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 ...
Four Points by Sheraton Chicago O'Hare Airport
10249 Irving Park Road Schiller Park IL
28.47 km from city center
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant ...
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
5460 North River Road Rosemont IL
25.73 km from city center
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 ...
Super 8 by Wyndham Chicago O'Hare Airport
2951 Touhy Ave Elk Grove Village IL
24.36 km from city center
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
3001 South Mannheim Road Des Plaines IL
23.81 km from city center
Book a stay at this business-friendly hotel in Des Plaines. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Quality Inn O'Hare Airport
3801 North Mannheim Road Schiller Park IL
29.44 km from city center
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 ...
Loews Chicago O'Hare Hotel
5300 N River Rd Rosemont IL
26.17 km from city center
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 ...
Holiday Inn Chicago North-Evanston by IHG
1501 Sherman Ave Evanston IL
21.09 km from city center
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 ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
28.49 km from city center
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
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.
Tue, Dec 22 - Wed, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$253 Roundtrip, found 6 days ago
$253
Roundtrip
found 6 days ago
Sat, Dec 19 - Wed, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$258 Roundtrip, found 6 days ago
$258
Roundtrip
found 6 days ago
Tue, Dec 22 - Sat, Dec 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$353 Roundtrip, found 6 days ago
$353
Roundtrip
found 6 days ago
Tue, Dec 22 - Sat, Dec 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$383 Roundtrip, found 6 days ago
$383
Roundtrip
found 6 days ago