South Loop Vacation Packages

Top Holiday Package Deals in South Loop

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,589

per person

Sep 21 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (4,714 reviews)

The room and hotel exceeded my expectations. The hotel was located in the best spot. I would definitely stay here again.

Reviewed on Jul 18, 2026

Level Chicago – Old Town

Downtown Chicago

CA $2,013

per person

Sep 22 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (501 reviews)

Level hotels are awesome

Reviewed on Jul 18, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,777

per person

Sep 21 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.2/10 Wonderful! (523 reviews)

Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!

Reviewed on Jul 17, 2026

Swissotel - Chicago

Downtown Chicago

CA $1,616

per person

Sep 21 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9/10 Wonderful! (3,435 reviews)

Great experience the staff was super friendly and the hotel location was just amazing right in downtown Chicago. I will definitely be staying there again..

Reviewed on Jul 18, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $2,050

per person

Sep 21 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (2,566 reviews)

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.

South Loop Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $265

CA $315 total

Aug 10 - Aug 11

includes taxes & fees

8/10 Very good! (10,222 reviews)

"Wonderful location - we were right across from Buckingham Fountain. From the 11th floor, we had a great view of the lake. Old style elegance. The a/c - heating system is of a different era. I would not book a lake side room during the height of the summer - I don't think the system could keep ..."

Reviewed on Jul 19, 2026

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

Fully refundableReserve now, pay when you stay

CA $215

CA $255 total

Aug 19 - Aug 20

includes taxes & fees

7.6/10 Good! (2,690 reviews)

"Misrepresentation of rooms I thought was at Bates Motel A/C in the window I’m from Louisiana and I have never seen a hotel room look that way I would never stay there ever in my life"

Reviewed on Jul 18, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

CA $367

CA $477 total

Aug 6 - Aug 7

includes taxes & fees

8.6/10 Excellent! (2,972 reviews)

"Average stay for the area"

Reviewed on Jul 19, 2026

See all 4,441 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 vacation package cost?

Starting from a low CA $1,589, 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.