Search Deals onSouth Loop Vacation Packages
South Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $397, price is now $282 per person
$282
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Glen Club
Save 100% on your flight
Price was $601, price is now $372 per person
$372
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and The Glen Town Center are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $682, price is now $445 per person
$445
per person
Dec 8 - Dec 12
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $745, price is now $490 per person
$490
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Save 100% on your flight
Price was $990, price is now $673 per person
$673
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Villa Christina
Greater Grand Crossing
Save 100% on your flight
Price was $1,357, price is now $950 per person
$950
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Wintrust Arena and Obama Presidential Center are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $820 per person
$820
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). 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
Save 100% on your flight
Price was $1,115, price is now $801 per person
$801
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 ...
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, Nov 2 - Mon, Nov 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Thu, Nov 26 - Fri, Nov 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 13 hours ago
$224
Roundtrip
found 13 hours ago
Sat, Nov 14 - Tue, Nov 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Fri, Nov 13 - Fri, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,074 Roundtrip, found 5 days ago
$1,074
Roundtrip
found 5 days ago
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