South Loop Vacations from ￥384,236

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    Save up to ￥109,000 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥512,734, price is now ￥384,236 per person
￥384,236
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
I loved everything about this hotel - the location- beautiful views!! Really comfortable bed! Very Clean and comfortable!

Reviewed on Jul 10, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥562,620, price is now ￥428,059 per person
￥428,059
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Good location.

Reviewed on Jul 3, 2026

The Drake

The Drake

4 out of 5
Downtown Chicago
Price was ￥492,440, price is now ￥385,570 per person
￥385,570
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,511 reviews)
Beau séjour! Bien situé, j’y reviendrais

Reviewed on Jul 10, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥505,210, price is now ￥395,874 per person
￥395,874
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,429 reviews)
The hotel staff was wonderful to deal with and met our travel needs with great rooms and vital city information!

Reviewed on Jul 8, 2026

Best Western Plus Hawthorne Terrace Hotel

Best Western Plus Hawthorne Terrace Hotel

3 out of 5
Lakeview
Price was ￥521,748, price is now ￥409,650 per person
￥409,650
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
staff at front counter was not rude. it not pleasant. just I would say indifferent.

Reviewed on Jul 10, 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
A busy city street with tall buildings, a bus, and cars.

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 ￥30,686 per night from Aug 10 to Aug 11
￥30,686
￥36,483 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (10,218 reviews)
"Our stay was great, best was comfortable and room was clean."

Reviewed on Jul 9, 2026

Congress Plaza Hotel
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 ￥25,426 per night from Aug 10 to Aug 11
￥25,426
￥30,229 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (2,687 reviews)
"nos hicieron esperar dos horas para hacer el check in porque no estaba lista la habitación"

Reviewed on Jul 10, 2026

Travelodge by Wyndham Downtown Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥45,298 per night from Jul 19 to Jul 20
￥45,298
￥58,621 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (2,943 reviews)
"Cleanliness and breakfast, however room service is poor."

Reviewed on Jul 9, 2026

Hilton Chicago
See all 4,451 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 ￥384,236, 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.

Stay near popular South Loop attractions

A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Soldier Field

8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,887
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,398
per adult
92% of travellers recommend
Art Institute of 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.