South Loop Vacations from NT$29,314

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The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
just found
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.2/10 Very Good! (3,512 reviews)
Very nice staff, food is ok, location is good, beds are super comfy!

Reviewed on 2025/8/8

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
just found
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (1,002 reviews)
The room is a little small for the price. However, it is a cute little hotel. The complimentary breakfast is barely average, but it's free. The staff was really nice. I appreciated how helpful they were when I asked questions. The fitness center is small barely has any equipment. Thankfully, it wasn't busy while I was in there. It's in a great spot to find nice places to eat and there is a Trader Joe's around the corner. Overall, it was a nice hotel. I would stay there again.

Reviewed on 2025/8/3

ACME Hotel Company

ACME Hotel Company

3.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
just found
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,746 reviews)
Central and walkable to the Magnificent Mile shopping, Navy Pier, Millenium Park, the Loop and many restaurants. Hotel is older but still comfortable. Parking available next door to hotel (public parking). Cute coffee shop and bakery in lobby and great tasting bar in hotel.

Reviewed on 2025/8/7

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 NT$7,474 per night from Sep 7 to Sep 8
NT$7,474
NT$8,773 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (8,914 reviews)
"I love it"

Reviewed on 2025/8/5

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$4,165 per night from Sep 3 to Sep 4
NT$4,165
NT$5,762 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (2,046 reviews)
"Perfect place to see the sights"

Reviewed on 2025/8/7

Hilton Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$2,831 per night from Aug 25 to Aug 26
NT$2,831
NT$3,324 total
Aug 25 - Aug 26
includes taxes & fees
7.2/10 Good! (2,267 reviews)
Stay for Lollalapoolza
"Absolutely amazing stay. I travel A LOT and this staff was the best hotel staff I have ever had (including mutli 5 star properties). Thank you for being a part of our great weekend."

Reviewed on 2025/8/5

Travelodge by Wyndham Downtown Chicago
See all 4,713 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$29,314, 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

Very nice terminal for the river taxi

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 fascinating museums.

Ping Tom Memorial Park
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

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