South Loop Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest South Loop Vacation Packages
- Sheraton Grand Chicago Riverwalk
Jan 21 - Jan 24Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,885 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,134CA $822found 1 day agoper traveller - Level Chicago Fulton Market
Dec 9 - Dec 15Level Chicago Fulton Market + Flight
Downtown Chicago6 nights4.0 star property9.2/10 - Wonderful (605 reviews)Roundtrip • Vancouver (YVR) - Chicago (ORD)YVR - ORD • 1 stop ORD - YVR • 1 stopCA $2,039CA $1,463found 1 day agoper traveller - Park Hyatt Chicago
Jan 21 - Jan 24Park Hyatt Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,002 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,801CA $1,316found 5 hours agoper traveller - Pendry Chicago
Jan 21 - Jan 24Pendry Chicago + Flight
Downtown Chicago3 nights4.5 star property9.2/10 - Wonderful (1,164 reviews)"The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."Reviewed November 8, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,344CA $984found 5 hours agoper traveller - The Talbott, Autograph Collection
Dec 17 - Dec 21The Talbott, Autograph Collection + Flight
Downtown Chicago4 nights4.5 star property9.4/10 - Exceptional (196 reviews)"I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure."Reviewed November 8, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,148CA $850found 1 day agoper traveller
Where to stay in South Loop
Downtown Chicago
Magnificent Mile
The Loop
River North
Lincoln Park
Discover the most popular places to visit in South Loop
What to do near South Loop
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour
South Loop Hotel Deals
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Every thing is good!👍🌹"
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop"The room was clean. There was only 1 working elevator which was annoying to wait for every time. Other than that everything was good."
"Great for extended stays."
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop
Hyatt Regency McCormick Place Chicago
Hyatt Regency McCormick Place Chicago"The safe didn’t lock. They promised to send someone to fix it, but they never did."
Frequently Asked Questions
How much does a South Loop vacation package cost?
Starting from a low CA $822, 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.