Southmoor Holidays from £847

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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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was £1,002, price is now £847 per person
£847
per person
23 Apr - 27 Apr
found 6 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (2,217 reviews)
Had a steak and ribs at the restaurant downstairs and both were delicious

Reviewed on 1 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,368, price is now £1,177 per person
£1,177
per person
13 Apr - 16 Apr
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.

Reviewed on 3 Mar 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,153, price is now £999 per person
£999
per person
13 Apr - 16 Apr
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on 3 Mar 2026

Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
Price was £1,223, price is now £1,063 per person
£1,063
per person
27 Apr - 4 May
found 9 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,286 reviews)
Staff was great! Embassy “extras” worth it! Hotel was just a bit outdated.

Reviewed on 1 Mar 2026

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop

3 out of 5
Downtown Chicago
Price was £1,640, price is now £1,442 per person
£1,442
per person
27 Apr - 4 May
found 9 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,290 reviews)
It was convenient , well decorated , and very customer service oriented. The location is great for Willis Tower. We stayed for one night and would stay again.

Reviewed on 7 Mar 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 featuring a city

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

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 £85 per night from 30 Mar to 31 Mar
£85
30 Mar - 31 Mar
includes taxes & fees
8/10 Very Good! (9,924 reviews)
Staff is very polite and friendly! Grant gardens and bus stops are very convenient. Beautiful views. Historical building and safe feeling.

Reviewed on 7 Mar 2026

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 £136 per night from 1 Apr to 2 Apr
£136
1 Apr - 2 Apr
includes taxes & fees
8.6/10 Excellent! (2,668 reviews)
Amazing place to stay!

Reviewed on 7 Mar 2026

Hilton 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 £136 per night from 5 Apr to 6 Apr
£136
5 Apr - 6 Apr
includes taxes & fees
8.6/10 Excellent! (2,319 reviews)
All good

Reviewed on 6 Mar 2026

Palmer House a Hilton Hotel
See all 2,458 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Southmoor travel package cost?
Custom make your Southmoor travel package from just £847. 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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 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

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£33
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
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. Flight-inclusive packages are ATOL protected.