South Loop Vacation Packages

Top Holiday Package Deals in South Loop

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

Level Chicago Fulton Market

Downtown Chicago

CA $1,061

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (533 reviews)

Will be back great experience room was amazing.

Reviewed on Jul 23, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,522

per person

Sep 27 - Oct 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,714 reviews)

Hotel Riu exceeded our expectations. The room was spacious and clean. There were no carpets in the room which was fabulous! The bed was comfortable and the room is equipped with key controlled lights and cooling. The hotel is very quiet and I had no trouble sleeping until the last night. There was a sound that mimicked a bass or subwoofer that kept me up. The staff did all they could to find the source including sending an engineer to my room to make sure it was nothing mechanical or internal. We never could find the source but it sounded far away not like in the next room. I felt very safe as a single woman traveling on my own. No access to upstairs rooms without a key card. Our favorite place was the rooftop bar!!!! Great views, fabulous staff, and the food was very tasty. Drinks were well made and not watered down.

Reviewed on Jul 24, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $1,151

per person

Sep 27 - Oct 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very good! (2,854 reviews)

We contacted the property about checking luggage early, no problem. Check in was quick as well as checking out. Markets and pharmacy about a block away. Restaurants, bars, pubs landmarks all within walking distance. Red line and brown line L train about 8 minute walk. Our room was a little small but was comfortable and had everything we needed, very clean and for being downtown surprisingly quiet. Would recommend and would return.

Reviewed on Jul 24, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,496

per person

Sep 2 - Sep 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (504 reviews)

We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure.

Reviewed on Jul 23, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,676

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,603 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

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.

South Loop Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $237

CA $282 total

Aug 13 - Aug 14

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

Fully refundableReserve now, pay when you stay

CA $197

CA $234 total

Aug 16 - Aug 17

includes taxes & fees

7.6/10 Good! (2,707 reviews)

"This is a charming, positive-energy, no-frills hotel. The staff is genuine, helpful, and kind. The location is convenient. While the property doesn't have all the bells and whistles of some of its competitors, it offers rooms with enough space to 'feel like home,' close proximity to restaurants at ..."

Reviewed on Jul 25, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $382

CA $496 total

Aug 6 - Aug 7

includes taxes & fees

8.6/10 Excellent! (2,996 reviews)

"The hotel was beautiful and astonishing. Definitely worth the visit."

Reviewed on Jul 25, 2026

See all 4,529 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 $1,061, 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.