South Loop Vacations from ₩629,036

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    Save up to ₩234,741 when you book a flight and hotel together*

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The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Spark by Hilton Des Plaines Chicago O'Hare

Spark by Hilton Des Plaines Chicago O'Hare

3 out of 5
Price was ₩745,824, price is now ₩629,036 per person
₩629,036
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (95 reviews)
I can’t believe they changed me $4.95 for internet!!!!

Reviewed on Mar 10, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ₩1,374,352, price is now ₩1,080,446 per person
₩1,080,446
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.4/10 Very Good! (2,231 reviews)
Everything went pretty well. Glad we choose to stay there.

Reviewed on Mar 15, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was ₩904,416, price is now ₩737,304 per person
₩737,304
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,785 reviews)
Everything was amazing

Reviewed on Mar 19, 2026

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

3 out of 5
Save 100% on your flight
Price was ₩2,752,098, price is now ₩2,251,751 per person
₩2,251,751
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
No reviews
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

4 out of 5
Price was ₩1,019,546, price is now ₩835,108 per person
₩835,108
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
Staff was great. The beds were small . We booked two queen beds and we got what felt like two full beds instead. The toilet was running when we got there but they sent someone up to fix it right away and it was fine after that.

Reviewed on Mar 11, 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 showing a city

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.

Find hotels in Downtown Chicago

South Loop Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩200,528 per night from Apr 2 to Apr 3
₩200,528
₩235,400 total
Apr 2 - Apr 3
includes taxes & fees
8/10 Very Good! (9,968 reviews)
Nice room, a bit disturbed I had to pay a safety fee of$25.00 for each day of my stay.

Reviewed on Mar 20, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is ₩194,811 per night from Apr 1 to Apr 2
₩194,811
₩272,544 total
Apr 1 - Apr 2
includes taxes & fees
8.6/10 Excellent! (2,693 reviews)
This hotel is awesome for visiting Chicago. The staff were consistently attentive, respectful and helpful with suggestions. The hotel room was clean and the view we had was fantastic. The pool and hot tub were relaxing — easy to access and get fresh towels. The only minor criticism was that the hotel ...

Reviewed on Mar 19, 2026

Hilton Chicago
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩175,208 per night from Apr 1 to Apr 2
₩175,208
₩205,677 total
Apr 1 - Apr 2
includes taxes & fees
8.8/10 Excellent! (1,918 reviews)
Beautiful views from room. Friendly helpful staff.

Reviewed on Mar 20, 2026

Hilton Garden Inn Chicago Downtown South Loop
See all 4,702 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 ₩629,036, 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.

Discover the most popular places to visit in South Loop

Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.