South Loop Holidays
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Your South Loop Holiday
Cafes, bars and pubs and history are just the start of the things waiting for you when you lock in a holiday package to South Loop. Whether you're craving adventure, relaxation or something else, this commercial neighbourhood is likely to have it. Not sure what to see and do during your trip to South Loop? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are good places to begin. Expedia will help you turn your ideal South Loop holiday into reality, whatever your budget or travel plans.
Our guide on 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.
The Loop
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Our pick of the best South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$169
8 Sept - 9 Sept
includes taxes & fees
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
AU$364
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,319 reviews)
"Clean rooms, friendly staff, and nice bar."
Reviewed on 24 Aug 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
AU$350
7 Sept - 8 Sept
includes taxes & fees
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 holiday package cost?
Starting from a low , a holiday 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 holiday 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 holiday?
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 holiday 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 holiday 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 holiday 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
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.
Photo by © Cesar Russ Photography
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
Field Museum of Natural History
9.4/10 (1,744 reviews)
A great destination for all the family, home to over 2 million artefacts on archaeology, history and science, from dinosaur bones to Egyptian mummies.
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.
Northerly Island Natural Area
8.6/10 (28 reviews)
Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.
Northerly Island
Commune with nature and explore the great outdoors at Northerly Island during your travels in Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.
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 theatre scene in this vibrant area.
Arie Crown Theater
8.0/10 (9 reviews)
You can get tickets for a performance at Arie Crown Theater during your stay in Chicago. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
AU$35
per adult
90% of travellers recommend
Chicago Sightseeing River and Lake Cruise
AU$66
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.