Southmoor Holidays from £953

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Your Southmoor Holiday

Prepare to experience Southmoor on your own terms with a custom Southmoor holiday package! Uncovering the best parts of this lively city is made easier with a base in a neighbourhood 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 holiday on Expedia.

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£953
per person
24 Dec - 29 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Nice property overall Room was very nice Location excellent

Reviewed on 19 Oct 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£1,634
per person
24 Dec - 30 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,441
per person
24 Dec - 29 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Toilet paper was sub par

Reviewed on 22 Oct 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,397
per person
24 Dec - 30 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,068
per person
24 Dec - 30 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
This is a great hotel

Reviewed on 21 Oct 2026

Where to stay in Southmoor

Find the best Southmoor areas and neighborhoods for the activities you enjoy most. Learn more about Southmoor
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Top hotels in Southmoor

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£95
11 Nov - 12 Nov
includes taxes & fees
8/10 Very good! (10,183 reviews)
"The staff is amazing, very knowledgeable and helpful. The only downside of my stay is the bed. It is super firm! No pillow top here."

Reviewed on 22 Oct 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
£142
22 Nov - 23 Nov
includes taxes & fees
Hilton Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL
Fully refundable
£103
22 Nov - 23 Nov
includes taxes & fees
Club Quarters Hotel, Central Loop, Chicago
See all 2,526 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.
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Frequently asked questions

How much does a Southmoor travel package cost?
Custom make your Southmoor travel package from just £953. Choose from any combination of flights, hotels and rental cars to put together the escape you've been dreaming about for ages. Be sure to add on a few experiences or activities!
If I'm not able to travel, can I cancel my Southmoor travel package?
Don't stress if you're rethinking your Southmoor travel package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally get that your circumstances can suddenly change, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Southmoor?
Book everything all in one place with our Southmoor travel packages. You'll discover deals on flights, hotels and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 air carriers and 1,000,000 properties globally to select from, you'll have the flexibility to mix and match as you please.
Does Expedia offer Book Now, Pay Later Southmoor holidays?
We certainly do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that suits you best during the checkout process and take away the stress of budgeting for your trip. Remember to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:
  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.
Where should I stay in Southmoor?
With fascinating attractions such as Orland Square and Space Golf in this neighbourhood, look for a hotel situated near either of them. Centennial Park Aquatic Centre is another Southmoor hot spot that pulls the crowds.
What are the top hotels in Southmoor?
Quality Inn & Suites Orland Park - Chicago and Homewood Suites by Hilton Orland Park are a couple of the most sought-after hotels in Southmoor. Why not look up the rates and facilities at each and then make up your mind?
How far in advance should I book my Southmoor holiday?
It's tricky picking the best time for airfares, but we generally suggest the earlier, the better. Plenty of international flights on Expedia become available to compare up to a year in advance. If you're booking late, fear not. Low prices appear from time to time just weeks before departure dates.
What does an Expedia Southmoor travel package include?
Flights, hotels and rental cars, or any combination of the three — it's your choice. Whether you're venturing to Southmoor with the whole family or travelling with your friends, there's a bundle to match your style and budget. Once you've made your booking, why not add on a few tours and experiences?
What should I know before booking a Southmoor travel package?
You'll pick up great savings when you bundle your hotels, flights and rental cars into a package. Not just that, booking everything in one spot simply makes planning easier. So why waste time or money? Whether you're organising an upscale romantic escape or an affordable family break, check out our travel packages today.
Can I choose my airline with a Southmoor Expedia travel package?
You can, and with more than 550 airlines to choose from around the world, you have loads of choice. Look through the available options and see which airline fits your needs and budget.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

£30
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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. Flight-inclusive packages are ATOL protected.