South Loop Vacations from NT$29,422

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The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$43,745, price is now NT$29,422 per person
NT$29,422
per person
May 15 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Big shoutout to Marina. Thank you for the hospitality and being so kind and helpful to me during my stay. Chicago is great!!

Reviewed on 2026/3/30

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,227, price is now NT$35,716 per person
NT$35,716
per person
May 15 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Friendly staff, nice breakfast!

Reviewed on 2026/3/31

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$72,381, price is now NT$50,602 per person
NT$50,602
per person
May 15 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.

Reviewed on 2026/3/31

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,844, price is now NT$43,198 per person
NT$43,198
per person
May 15 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Wonderful location Nicely updated and appointed rooms. Quiet. Quick elevator. Excellent restaurant on site. Great value for money. Very helpful staff.

Reviewed on 2026/3/29

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$49,006, price is now NT$34,831 per person
NT$34,831
per person
May 15 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 2026/3/9

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

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 NT$3,717 per night from Apr 5 to Apr 6
NT$3,717
NT$4,363 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,028 reviews)
very old and grand hotel. felt like i was in the titanic but a hotel. Was very eerie and felt haunted. if you are in to ghost wonderful place to stay. the stairs alone are just breath taking.

Reviewed on 2026/3/31

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$5,090 per night from Apr 5 to Apr 6
NT$5,090
NT$6,915 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (2,705 reviews)
Great location, iconic hotel.

Reviewed on 2026/3/31

Hilton Chicago
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
500 South Dearborn Street Chicago IL
The price is NT$4,072 per night from Apr 27 to Apr 28
NT$4,072
NT$4,780 total
Apr 27 - Apr 28
includes taxes & fees
9.6/10 Exceptional! (1,227 reviews)
I will definitely stay at Hotel Blake again! The staff was super friendly, especially David, who checked us in at 4 a.m. after our flight was delayed 8 hours. The room was surprisingly big and pretty quiet for a Loop hotel, the decor is beautiful, the bed was super comfortable, and the bathroom was ...

Reviewed on 2026/3/31

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
See all 4,655 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 NT$29,422, 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

Ping Tom Memorial Park

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Ping Tom Memorial Park
Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline at North Beach

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.