South Loop Vacation Packages
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Top Holiday Package Deals in South Loop
Price found within the past 48 hours. Click for updated prices.
Victoria Resort and Bed & Breakfast
North Side
CA $1,785
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (154 reviews)
This is a lovely place to stay with great amenities and special touches. The breakfast was amazing! Highly recommend this gem just 2 blocks from the beach and easy bike ride to downtown. The owner is onsite and very friendly.
Reviewed on Oct 10, 2026
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
CA $1,337
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,491 reviews)
The room was very nice. The kitchen had dish towels and soap for the dishwasher. Loved the full size refrigerator too.
Reviewed on Oct 19, 2026
Where to stay in South Loop
Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $147
CA $175 total
Nov 10 - Nov 11
includes taxes & fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $238
CA $325 total
Nov 20 - Nov 21
includes taxes & fees
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
Fully refundableReserve now, pay when you stay
CA $202
CA $237 total
Nov 9 - Nov 10
includes taxes & fees
9/10 Wonderful! (1,379 reviews)
"I would give this place 4 stars if it wasn’t for the lack of cleanliness. The shower had a lot of grime in the seams and there was hair on the living room floor. There were stains on the couch and it was riddled with crumbs under the cushions. They also don’t use a real duvet cover, just a flat sheet ..."
Reviewed on Oct 20, 2026
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.
Frequently asked questions
How much does a South Loop vacation package cost?
Starting from a low CA $847, a vacation package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to South Loop?
Creating your own South Loop vacation package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you'll have no trouble creating your next dream getaway.
Where should I stay in South Loop?
Make sightseeing a breeze by staying someplace close to South Loop's iconic attractions. McCormick Place and Millennium Park are two of the best in the area.
What are the top hotels in South Loop?
Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?
How far in advance should I book my South Loop vacation?
It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you're hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.
What does an Expedia South Loop travel package include?
That depends on what type of getaway you're thinking about. South Loop vacation deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a South Loop travel package?
So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a South Loop Expedia vacation package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that's a good fit for your needs.
If I'm not able to travel, can I cancel my South Loop vacation package?
Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
Stay near popular South Loop attractions
McCormick Place
8.8/10 (9,822 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Photo by City Of Chicago
Field Museum of Natural History
9.4/10 (1,744 reviews)
Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.
Adler Planetarium and Astronomy Museum
8.8/10 (248 reviews)
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Arie Crown Theater
8.0/10 (9 reviews)
You can enjoy a show at Arie Crown Theater on your trip to Chicago. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Columbia College Chicago
8.4/10 (164 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Dearborn Station
8.8/10 (15 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Things to do
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
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- Willis Tower
- Visit Downtown Chicago
- Ernest Hemingway Museum and House
- Griffin Museum of Science and Industry
- Art Institute of Chicago
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- Ann and Robert H. Lurie Children's Hospital
- Visit Chicago
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- Lincoln Park Zoo
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- Garfield Park Conservatory
- Robie House
- Marina City
- Navy Pier
- 875 North Michigan Avenue
- Northwestern University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.