South Loop Holidays & Package Deals

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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

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 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.

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$324

10 Aug - 11 Aug

includes taxes & fees

8/10 Very good! (10,218 reviews)

"Our stay was great, best was comfortable and room was clean."

Reviewed on 9 July 2026

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

Fully refundableReserve now, pay when you stay

AU$268

10 Aug - 11 Aug

includes taxes & fees

7.6/10 Good! (2,687 reviews)

"nos hicieron esperar dos horas para hacer el check in porque no estaba lista la habitación"

Reviewed on 10 July 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

AU$434

19 July - 20 July

includes taxes & fees

8.6/10 Excellent! (2,943 reviews)

"Cleanliness and breakfast, however room service is poor."

Reviewed on 9 July 2026

See all 4,453 properties in South Loop

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.