South Loop 2026 Holidays & City Breaks | Flight + Hotel

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Sleep Inn & Suites Oregon - Madison

€2,956

per person

17 Dec - 22 Dec

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (471 reviews)

I was just looking for a clean well kept hotel for a wedding I was attending and I found it in this hotel. Great clean typical hotel room with comfortable beds. Pool looked nice and breakfast was good! Highly recommended!

Reviewed on 31 Oct 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

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

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.

Top hotels in South Loop

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

€124

10 Nov - 11 Nov

includes taxes & fees

8/10 Very good! (10,075 reviews)

"There’s mold growing by the heaters. Behind the bed was unclean, seemed as someone left a towel or shirt left behind the bed. The halls smelled marijuana, the carpet was dirty, stains on the wall, toilet seemed to have plumbing issues and was not stable to the floor. The bathroom didn’t seem clean. ..."

Reviewed on 1 Nov 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

€141

27 Nov - 28 Nov

includes taxes & fees

Sentral Michigan Avenue

808 SOUTH MICHIGAN AVENUE Chicago IL

Fully refundableReserve now, pay when you stay

€142

22 Nov - 23 Nov

includes taxes & fees

9/10 Wonderful! (1,397 reviews)

"Great views and front desk service"

Reviewed on 31 Oct 2026

See all 4,673 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 €2,956, 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

A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

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.

See properties