South Loop Vacation Packages

Top Holiday Package Deals in South Loop

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

Chicago Marriott Suites Deerfield

CA $755

per person

Aug 24 - Aug 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (1,015 reviews)

Great customer service, very clean , big room

Reviewed on Jun 26, 2026

Level Chicago – Old Town

Downtown Chicago

CA $2,438

per person

Sep 12 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (495 reviews)

Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $975

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (504 reviews)

Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

Level Chicago - River North

Downtown Chicago

CA $1,956

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (1,013 reviews)

Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $919

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (126 reviews)

Always a pleasure and a great location

Reviewed on Jun 24, 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

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 $194

CA $230 total

Jun 30 - Jul 1

includes taxes & fees

8/10 Very good! (10,160 reviews)

"Friendly staff. Encountered a cockroach in the elevator."

Reviewed on Jun 29, 2026

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

Fully refundableReserve now, pay when you stay

CA $192

CA $228 total

Jul 8 - Jul 9

includes taxes & fees

7.6/10 Good! (2,643 reviews)

"Everything was perfect"

Reviewed on Jun 29, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $339

CA $445 total

Jun 30 - Jul 1

includes taxes & fees

8.6/10 Excellent! (2,891 reviews)

"Nice and convenient location great location."

Reviewed on Jun 28, 2026

See all 4,698 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 $755, 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.