Southmoor Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Price was €700, price is now €545 per person
€545
per person
2 Jan - 6 Jan
found 18 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Staff were very pleasant and helpful. We will definitely be back.

Reviewed on 26 Nov 2025

Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Price was €2,363, price is now €1,753 per person
€1,753
per person
2 Jan - 6 Jan
found 18 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on 26 Nov 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was €723, price is now €558 per person
€558
per person
2 Jan - 6 Jan
found 18 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
The staff was amazing, as always. The rooms were clean and comfortable.

Reviewed on 2 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was €719, price is now €558 per person
€558
per person
2 Jan - 6 Jan
found 18 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on 26 Nov 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €755, price is now €594 per person
€594
per person
2 Jan - 6 Jan
found 18 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Inviting lobby area with comfortable bar on the side. Excellent cocktails! 19th floor room with roomy bathroom & excellent water pressure. Soft, comfortable sheets on moderately firm mattresses. Very prompt room service with nice choices 24/7 (we ordered at midnight). Located about 2 blocks from Miracle Mile. On top of that, customer service was outstanding!

Reviewed on 1 Dec 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 which includes 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

Top hotels in Southmoor

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 €98 per night from 5 Dec to 6 Dec
€98
5 Dec - 6 Dec
includes taxes & fees
8/10 Very Good! (9,664 reviews)
Nice rooms, great price

Reviewed on 27 Nov 2025

Congress Plaza Hotel
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 €126 per night from 28 Dec to 29 Dec
€126
28 Dec - 29 Dec
includes taxes & fees
8.4/10 Very Good! (2,111 reviews)
Absolutely gorgeous! This hotel offers everything you need and want. Excellent food, amenities and the spa is the best part. We had a mother and daughter weekend with massage's, it was what we hoped for and more.

Reviewed on 29 Nov 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundable
The price is €128 per night from 29 Dec to 30 Dec
€128
29 Dec - 30 Dec
includes taxes & fees
8.8/10 Excellent! (1,708 reviews)
Bbb

Reviewed on 27 Nov 2025

Crowne Plaza Chicago West Loop by IHG
See all 2,490 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 holiday package cost?
Less than you might think — from as low as €545, 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 holiday 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 holiday package with your name on it.
Where should I stay in Southmoor?
With fascinating attractions such as Orland Square and Centennial Park Aquatic Centre in this neighbourhood, 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 holiday?
You'll be rewarded with the biggest variety at the lowest prices by booking your holiday 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 holiday!
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 organising a fancy romantic getaway or a low-cost family break, explore our package deals today.
Can I choose my airline with a Southmoor Expedia holiday 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 holiday.
If I'm not able to travel, can I cancel my Southmoor holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Southmoor holiday 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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

Navy Pier

4/5(125 reviews)

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

Navy Pier

Things to do

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€39
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.