Search Deals onSouth Loop Vacation Packages
South Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
W Chicago - Lakeshore
Downtown Chicago
per person
Feb 10 - Feb 16
found 4 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Waldorf Astoria Chicago
Downtown Chicago
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Aloft Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
3-4 Night Vacations in South Loop
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in South Loop
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in South Loop
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
Save an average of 15% on thousands of hotels when you're signed in
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
River Hotel
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Feb 3 - Wed, Feb 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Mon, Jan 27 - Sat, Feb 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$936 Roundtrip, found 5 hours ago
$936
Roundtrip
found 5 hours ago
Fri, Jan 24 - Sun, Feb 2
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$2,043 Roundtrip, found 6 days ago
$2,043
Roundtrip
found 6 days ago
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