Kildeer Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Kildeer Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $662, price is now $499 per person
$499
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Nice environment and very reasonable prices..right downtown so great location!
Reviewed on Nov 5, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,200, price is now $781 per person
$781
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
El mejor lugar para quedarte en Chicago⭐️
Reviewed on Nov 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,923, price is now $1,411 per person
$1,411
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop 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.
Swissotel - Chicago
Downtown Chicago
Price was $889, price is now $659 per person
$659
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Breakfast was good
Reviewed on Nov 4, 2026
The Blackstone, Autograph Collection
Downtown Chicago
Price was $853, price is now $637 per person
$637
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
The Talbott, Autograph Collection
Downtown Chicago
Price was $766, price is now $576 per person
$576
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Top Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
24.52 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
26.73 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
26.19 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
26.28 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 ...
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
5460 North River Road Rosemont IL
26.23 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 ...
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
23.25 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
27.49 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 ...
Super 8 by Wyndham Chicago O'Hare Airport
2951 Touhy Ave Elk Grove Village IL
20.36 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
23.37 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
28.22 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
26.58 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 ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
21.11 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 ...
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
28.5 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 breakfast 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, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$331 Roundtrip, found 5 days ago
$331
Roundtrip
found 5 days ago