Search Deals onSouth Loop Vacation Packages
South Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Save 100% on your flight
Price was $555, price is now $398 per person
$398
per person
May 9 - May 13
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
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 clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
La Banque Hotel
Price was $810, price is now $609 per person
$609
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago – Old Town
Downtown Chicago
Price was $1,008, price is now $776 per person
$776
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $936, price is now $601 per person
$601
per person
May 10 - May 14
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,019, price is now $664 per person
$664
per person
Apr 28 - May 3
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) 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 restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $774, price is now $517 per person
$517
per person
Apr 28 - May 3
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $974, price is now $668 per person
$668
per person
Apr 28 - May 3
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $805, price is now $571 per person
$571
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
The Blackstone, Autograph Collection
636 S Michigan Ave Chicago IL
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 ...
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 ...
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, Apr 22 - Wed, May 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 1 hour ago
$131
Roundtrip
found 1 hour ago
Wed, Apr 15 - Mon, Apr 20
LAX
Los Angeles Intl.
MDW
Midway Intl.
$230 Roundtrip, found 1 hour ago
$230
Roundtrip
found 1 hour ago
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$532 Roundtrip, found 13 hours ago
$532
Roundtrip
found 13 hours ago
Mon, Apr 13 - Sat, May 2
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,066 Roundtrip, found 3 hours ago
$1,066
Roundtrip
found 3 hours ago
Discover Other Travel Deals
- McCormick Place Vacations
- Grant Park Vacations
- Soldier Field Vacations
- Field Museum of Natural History Vacations
- Wintrust Arena Vacations
- Adler Planetarium and Astronomy Museum Vacations
- Northerly Island Natural Area Vacations
- Columbia College Chicago Vacations
- Arie Crown Theater Vacations
- Dearborn St Station Vacations