Search Deals onSouth Loop Vacation Packages
South Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
Save 100% on your flight
Price was $397, price is now $250 per person
$250
per person
Feb 21 - Feb 26
found 11 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Hyatt Regency Lisle near Naperville
Price was $612, price is now $409 per person
$409
per person
Feb 14 - Feb 22
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Four Columns at Morton Arboretum and Belmont Prairie Nature Preserve are located nearby.
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
Price was $470, price is now $270 per person
$270
per person
Feb 21 - Feb 26
found 11 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. 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 Clark Street Beach and Halim Time & Glass Museum are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $609, price is now $375 per person
$375
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Illinois Beach Hotel
Save 100% on your flight
Price was $432, price is now $269 per person
$269
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,530, price is now $1,610 per person
$1,610
per person
Feb 3 - Feb 8
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $583, price is now $372 per person
$372
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
La Banque Hotel
Save 100% on your flight
Price was $1,047, price is now $672 per person
$672
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park 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
Hilton Chicago
720 S Michigan Ave Chicago IL
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 ...
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street Chicago IL
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 ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
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 ...
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.
Wed, Feb 11 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 22 hours ago
$153
Roundtrip
found 22 hours ago
Tue, Jan 13 - Fri, Jan 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$518 Roundtrip, found 6 days ago
$518
Roundtrip
found 6 days ago
Wed, Mar 4 - Mon, Mar 16
PVG
Pudong Intl.
ORD
O'Hare Intl.
$951 Roundtrip, found 6 days ago
$951
Roundtrip
found 6 days ago
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