West Loop Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
West Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $993, price is now $687 per person
$687
per person
Mar 22 - Mar 27
found 17 hours ago
Roundtrip flight included
Norfolk (ORF) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,798, price is now $1,235 per person
$1,235
per person
Mar 22 - Mar 27
found 14 hours ago
Roundtrip flight included
Norfolk (ORF) 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.
Level Chicago Fulton Market
Downtown Chicago
Price was $962, price is now $703 per person
$703
per person
Mar 22 - Mar 27
found 6 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was $1,201, price is now $914 per person
$914
per person
Mar 22 - Mar 27
found 16 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this spa 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.
Level Chicago – Old Town
Downtown Chicago
Price was $941, price is now $718 per person
$718
per person
Mar 22 - Mar 27
found 16 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,026, price is now $797 per person
$797
per person
Mar 22 - Mar 27
found 17 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Top Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
0.41 km from West Loop
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
The Emily Hotel
311 North Morgan Street Chicago IL
0.6 km from West Loop
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 ...
Hyatt House Chicago West Loop
105 N MAY STREET Chicago IL
0.34 km from West Loop
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
0.38 km from West Loop
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
1.27 km from West Loop
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
2.4 km from West Loop
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 ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
2.7 km from West Loop
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 ...
Hilton Chicago
720 S Michigan Ave Chicago IL
2.47 km from West Loop
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 ...
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
2.31 km from West Loop
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 O'Hare Airport
O'Hare International Airport Chicago IL
23.43 km from West Loop
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 ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
3.18 km from West Loop
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 ...
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
2.84 km from West Loop
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
2.93 km from West Loop
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and 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.
Sat, May 30 - Tue, Jun 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Wed, May 27 - Sat, May 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Tue, Apr 7 - Wed, Apr 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Tue, Apr 7 - Wed, Apr 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Tue, Apr 7 - Wed, Apr 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago