South Loop Vacations from ￥467,514

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The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥581,062, price is now ￥467,514 per person
￥467,514
per person
Sep 28 - Oct 4
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (339 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug 27, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥785,838, price is now ￥569,447 per person
￥569,447
per person
Sep 28 - Oct 4
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Great location but a busy area

Reviewed on Aug 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥716,471, price is now ￥542,934 per person
￥542,934
per person
Sep 28 - Oct 4
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug 25, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥670,676, price is now ￥530,761 per person
￥530,761
per person
Sep 28 - Oct 4
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥590,428, price is now ￥473,178 per person
￥473,178
per person
Sep 28 - Oct 4
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug 25, 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 ￥19,833 per night from Sep 1 to Sep 2
￥19,833
￥23,283 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,016 reviews)
"I really enjoyed my stay here . The hotel is very historical and is known for hosting beautiful weddings, it’s huge , restaurants on property, and is very close to everything there is to see in downtown Chicago . Very close to the river walk , millennium park, coffee shops/breakfast, the loop , Taco ..."

Reviewed on Aug 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 ￥20,670 per night from Sep 2 to Sep 3
￥20,670
￥28,601 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (2,112 reviews)
good stay except for Wi-fi
"The Wi-Fi connection was spotty and could not connect to necessary sites. There was an error in the network messages repeatedly."

Reviewed on Aug 25, 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 ￥17,151 per night from Sep 2 to Sep 3
￥17,151
￥20,131 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (2,303 reviews)
"Location was awesome. Staff was so nice and helpful. Rooms were really clean. Nothing bad to say about the whole stay here!"

Reviewed on Aug 24, 2025

Travelodge by Wyndham Downtown Chicago
See all 4,650 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 ￥467,514, 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

4.5/5(1,256 reviews)

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

4.5/5(186 reviews)

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

4/5(122 reviews)

Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the entertainment choices 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

￥1,441
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

￥9,297
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
Picture 2 for Activity Chicago: Ghost Bus Tour of Haunted Locations

Chicago: Ghost Bus Tour of Haunted Locations

￥7,981
per adult
100% of travellers recommend
Chicago: Ghost Bus Tour of Haunted Locations
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.