South Loop Vacations from ￥223,048

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The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥263,537, price is now ￥223,048 per person
￥223,048
per person
Nov 28 - Nov 30
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast buffet was excellent. Shortage of cleaning staff created some problems—two times the room wasn’t serviced until after 5:00 p.m. Room was fine but we needed information about turning on and using the TV. Also needed instructions on using the soap dispensers in the bathroom. Seems trivial, but it’s the little things that separate good from excellent. Staff was cordial and helpful.

Reviewed on Sep 27, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥280,959, price is now ￥226,887 per person
￥226,887
per person
Dec 3 - Dec 8
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay

Reviewed on Sep 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥320,939, price is now ￥259,332 per person
￥259,332
per person
Nov 28 - Nov 30
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe

Reviewed on Sep 27, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥281,081, price is now ￥232,163 per person
￥232,163
per person
Dec 3 - Dec 8
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
Great room. Very nice staff. We loved it. The scent in the lobby was nice but a little strong. I would stay here again.

Reviewed on Sep 27, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ￥314,524, price is now ￥269,952 per person
￥269,952
per person
Nov 28 - Nov 30
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Great place to stay.

Reviewed on Sep 20, 2025

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 ￥20,081 per night from Oct 26 to Oct 27
￥20,081
￥23,573 total
Oct 26 - Oct 27
includes taxes & fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on Sep 25, 2025

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 ￥27,494 per night from Oct 23 to Oct 24
￥27,494
￥36,663 total
Oct 23 - Oct 24
includes taxes & fees
8.4/10 Very Good! (2,217 reviews)
"Great!"

Reviewed on Sep 26, 2025

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 ￥17,281 per night from Oct 20 to Oct 21
￥17,281
￥20,286 total
Oct 20 - Oct 21
includes taxes & fees
7.2/10 Good! (2,360 reviews)
"The location was honestly perfect! It was not far from the train station either coming from out of town. The train was my go-to transportation to get around. My room had a view of the Willis tower which was pretty cool. It’s an older building and nothing fancy, it was simple and had everything I ..."

Reviewed on Sep 18, 2025

Travelodge by Wyndham Downtown Chicago
See all 4,541 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 ￥223,048, 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

Soldier Field featuring a skyscraper, modern architecture and a city

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Adler Planetarium and Astronomy Museum showing modern architecture

Adler Planetarium and Astronomy Museum

Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.

Adler Planetarium and Astronomy Museum

Columbia College Chicago

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.

Columbia College Chicago

Things to do

Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

￥1,447
per adult
98% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

￥9,330
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
Big Bus Chicago Essential Ticket + 360 Chicago

Big Bus Chicago Essential Ticket + 360 Chicago

￥12,471
per adult
Big Bus Chicago Essential Ticket + 360 Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.