Southmoor Vacations from ￥65,215

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The Latest Southmoor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥105,626, price is now ￥65,215 per person
￥65,215
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
I had an amazing experience here! The staff—from valet to front desk to restaurant—was incredibly courteous, and Nate at the bar was a standout! My room was spotless, housekeeping was proactive, and guest services were top-tier. The area around the hotel is packed with restaurants, bars, and convenience stores—super walkable and fun. Only two minor cons: the terrace closes at 10 PM (wish it stayed open later), and the pool was closed during my visit. Still, this place blew me away. Highly recommend!

Reviewed on Aug 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥159,570, price is now ￥92,520 per person
￥92,520
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
. Loud staff, one hair in the shower…great location, night staff at front desk and bar were AMAZING

Reviewed on Aug 31, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥187,861, price is now ￥109,792 per person
￥109,792
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug 29, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥154,182, price is now ￥90,752 per person
￥90,752
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,192 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 – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥128,792, price is now ￥76,757 per person
￥76,757
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (343 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

Where to stay in Southmoor

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

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 ￥28,984 per night from Sep 15 to Sep 16
￥28,984
￥34,024 total
Sep 15 - Sep 16
includes taxes & fees
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 ￥27,045 per night from Sep 14 to Sep 15
￥27,045
￥36,065 total
Sep 14 - Sep 15
includes taxes & fees
Hilton Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥18,151 per night from Sep 14 to Sep 15
￥18,151
￥21,308 total
Sep 14 - Sep 15
includes taxes & fees
Club Quarters Hotel, Central Loop, Chicago
See all 2,314 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 ￥65,215, 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.

Discover the most popular places to visit in Southmoor

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
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

￥6,127
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥5,986
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,651
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.