Southmoor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Southmoor Vacation

Prepare to experience Southmoor on your own terms with a custom Southmoor vacation package! Uncovering the best parts of this lively city is made easier with a base in a neighborhood such as Flossmoor, which is good for golfing, among other things. You'll want to do a little exploring during your trip to Southmoor. Don't miss leading attractions such as Orland Park Sportsplex, Orland Square and Centennial Park. A couple of quick clicks is all it takes to put together a tailored Southmoor vacation on Expedia.

Top Holiday Package Deals in Southmoor

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Price was CA $1,042, price is now CA $809 per person
CA $809
per person
Dec 30 - Jan 4
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,307 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,281, price is now CA $1,610 per person
CA $1,610
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,117, price is now CA $818 per person
CA $818
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,217, price is now CA $919 per person
CA $919
per person
Jan 24 - Jan 26
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)

Where to stay in Southmoor

Find the best Southmoor areas and neighborhoods for the activities you enjoy most. Learn more about Southmoor
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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 CA $165 per night from Nov 24 to Nov 25
CA $165
CA $197 total
Nov 24 - Nov 25
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 CA $193 per night from Nov 22 to Nov 23
CA $193
CA $271 total
Nov 22 - Nov 23
includes taxes & fees
Hilton Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Nov 22 to Nov 23
CA $198
CA $236 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"A"

Reviewed on Nov 12, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
See all 2,414 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Southmoor vacation package cost?
Less than you might think — from as low as CA $809, 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

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
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.