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South Loop Vacation Packages

South Loop Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $452, price is now $250 per person
$250
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star golf hotel in Downers Grove. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Morton Arboretum and Yorktown Shopping Center are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,136, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $889, price is now $480 per person
$480
per person
Dec 3 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $608, price is now $329 per person
$329
per person
Dec 3 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,116, price is now $660 per person
$660
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $935, price is now $561 per person
$561
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $856, price is now $520 per person
$520
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.

3-4 Night Vacations in South Loop

Price found within the past 48 hours. Click for updated prices.
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
Save 100% on your flight
Price was $422, price is now $242 per person
$242
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,095, price is now $663 per person
$663
per person
Nov 26 - Nov 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $716, price is now $441 per person
$441
per person
Nov 26 - Nov 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
Save 100% on your flight
Price was $374, price is now $245 per person
$245
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

5-7 Night Vacations in South Loop

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $452, price is now $250 per person
$250
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,027, price is now $470 per person
$470
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $705, price is now $360 per person
$360
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,136, price is now $585 per person
$585
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in South Loop

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
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 ...
Opens in a new windowCongress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
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 ...
Opens in a new windowHilton Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
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 ...
Opens in a new windowTravelodge by Wyndham Downtown Chicago
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Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
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 ...
Opens in a new windowHilton Garden Inn Chicago Downtown South Loop
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
Opens in a new windowSentral Michigan Avenue
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
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 ...
Opens in a new windowBest Western Grant Park Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
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 ...
Opens in a new windowHilton Chicago/Magnificent Mile Suites
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
Opens in a new windowFreehand Chicago
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.

Frontier Airlines
Fri, Nov 14 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $74 found 1 day ago
Spirit Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $110 found 3 hours ago
Frontier Airlines
Thu, Oct 30 - Mon, Nov 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Los Angeles Intl. to Midway Intl., returning Mon, Nov 3, priced at $170 found 5 days ago
All Nippon Airways
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 2 days ago
$999
Roundtrip
found 2 days ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $999 found 2 days ago