Southmoor Vacations from ￥346,230

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    Save up to ￥109,000 when you book a flight and hotel together*

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The Latest Southmoor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥415,892, price is now ￥346,230 per person
￥346,230
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Great location, great space in the rooms!!

Reviewed on Jun 21, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥460,246, price is now ￥373,894 per person
￥373,894
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Terrible attitude of the front desk clerk. Room smelled bad, dirty carpet.

Reviewed on Jun 24, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥464,064, price is now ￥379,842 per person
￥379,842
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo

Reviewed on Jun 23, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was ￥488,708, price is now ￥407,436 per person
￥407,436
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable. The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.

Reviewed on Jun 21, 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was ￥415,138, price is now ￥353,784 per person
￥353,784
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,047 reviews)
PROS: Very clean rooms. Good shower pressure/temp. Convenient location to Millennium Park. Staff allowed us to store our bags for arrival and departure. CONS: Extremely noisy elevator kept us awake, definitely needed maintenance of some kind. Door to enter bathroom was quite a heavy slider and does run the risk of pinching your fingers.

Reviewed on Jun 23, 2026

Where to stay in Southmoor

Find the best Southmoor areas and neighborhoods for the activities you enjoy most. Learn more about Southmoor
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

Southmoor 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 ￥22,064 per night from Jun 29 to Jun 30
￥22,064
￥26,231 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,189 reviews)
"I liked the property and level of personnel. Two days I attempted to eat in their, in person restaurant and was given unrealistic wait times. 45 minutes and still didn't receive food after an hour and a half. I canceled the order and was late to my event. Also there is no on-site parking. The website ..."

Reviewed on Jun 25, 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 ￥22,858 per night from Jul 8 to Jul 9
￥22,858
￥27,176 total
Jul 8 - Jul 9
includes taxes & fees
7.6/10 Good! (2,632 reviews)
"It needs a remodelation , it needs upgrade ,It's a bit neglected. The good thing is the location and downstairs you it has a breakfast restaurant"

Reviewed on Jun 24, 2026

Travelodge by Wyndham Downtown Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥35,816 per night from Jul 9 to Jul 10
￥35,816
￥47,391 total
Jul 9 - Jul 10
includes taxes & fees
8.6/10 Excellent! (2,496 reviews)
"Prepaid parking through Expedia not honored at the hotel. Staff completely unhelpful in sorting this issue out. Forced to double pay for parking. Rooms dated with older furnishings. Beds old. Plumbing drained poorly. Location nice but otherwise I would not recommend."

Reviewed on Jun 22, 2026

Palmer House a Hilton Hotel
See all 2,478 properties in Southmoor
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 Southmoor vacation package cost?
Less than you might think — from as low as ￥346,230, as a matter of fact! By combining hotels, flights and car rentals into a custom-made package, your getaway to Southmoor is just a few clicks away.
How do I get a cheap travel package to Southmoor?
Our Southmoor vacation packages promise plenty of savings for the savvy globetrotter. For the best deals, simply bundle your hotel, flights and tours into an affordable package. But low prices are just the beginning of your next awesome adventure. When you book with Expedia, you'll have more than 550 airlines and 1,000,000 hotels across the globe to pick from. Whatever your budget or style, there's a vacation package with your name on it.
Where should I stay in Southmoor?
With fascinating attractions such as Orland Square and Centennial Park Aquatic Center in this neighborhood, look for a hotel situated near them. University Of Chicago Medicine is another sight in Southmoor that draws the crowds.
How far in advance should I book my Southmoor vacation?
You'll be rewarded with the biggest variety at the lowest prices by booking your vacation to Southmoor nice and early. Air carriers generally sell flight tickets anywhere up to a year in advance, so secure your spot ASAP. Having said that, Expedia is dedicated to giving you the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Southmoor travel package include?
Travel packages include rental cars, hotels and flights, but you can mix and match them to create your dream Southmoor trip. You can also add on fun stuff like tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Southmoor travel package?
You'll score big savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one spot just makes things easier. So why waste your time or money? Whether you're organizing a fancy romantic getaway or a low-cost family break, explore our package deals today.
Can I choose my airline with a Southmoor Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just choose the carrier that suits you and put together your ideal Southmoor vacation.
If I'm not able to travel, can I cancel my Southmoor vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Southmoor vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,887
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,398
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,478
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.