South Loop Vacation Packages
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Top Holiday Package Deals in South Loop
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
CA $1,696
per person
Sep 19 - Sep 25
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.
Reviewed on Aug 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,126
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.
Reviewed on Aug 14, 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
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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $145
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $258
CA $348 total
Sep 1 - Sep 2
includes taxes & fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $235
CA $320 total
Sep 7 - Sep 8
includes taxes & fees
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 $675, 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.
Stay near popular South Loop attractions
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
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.
Photo by City Of Chicago
Field Museum of Natural History
9.4/10 (1,744 reviews)
Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.
Adler Planetarium and Astronomy Museum
8.8/10 (248 reviews)
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Northerly Island Natural Area
8.6/10 (28 reviews)
Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Columbia College Chicago
8.4/10 (164 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.
Arie Crown Theater
8.0/10 (9 reviews)
You can enjoy a show at Arie Crown Theater on your trip to Chicago. Experience the fascinating museums and acclaimed theater scene in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
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- Willis Tower
- Visit Downtown Chicago
- Ernest Hemingway Museum and House
- Griffin Museum of Science and Industry
- Art Institute of Chicago
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- Water Tower Place
- Chicago Riverwalk
- Montrose Beach
- Golf Vacations
- Millennium Park
- Frank Lloyd Wright Historic District
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- Visit The Loop
- International Museum of Surgical Science
- Buckingham Fountain
- Grant Park
- United Center
- Ann and Robert H. Lurie Children's Hospital
- Visit Chicago
- Unity Temple
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- Visit Magnificent Mile
- Lincoln Park Zoo
- Chicago Theatre
- Chicago Vacations
- The Loop Vacations
- Garfield Park Conservatory
- Robie House
- Marina City
- Navy Pier
- 875 North Michigan Avenue
- Northwestern University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.