Southmoor Holidays from £952

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,259, price is now £952 per person
£952
per person
7 Sept - 11 Sept
found 13 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Breakfast was fantastic loved the options & how helpful & fast everyone was

Reviewed on 22 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,360, price is now £1,623 per person
£1,623
per person
11 Sept - 17 Sept
found 18 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,468, price is now £1,195 per person
£1,195
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)
This hotel is truly exceptional, and I must admit it has become my favorite. It surpassed all my expectations. The room was thoughtfully equipped with every conceivable amenity. The bathroom featured a generously sized tub, which I particularly enjoyed, and a television conveniently integrated into the mirror for viewing while bathing. Ice was already provided in the refrigerator, and the robes were wonderfully plush. The view was splendid. The room also included a stove, dishes, and a dishwasher. They even provided umbrellas, which proved incredibly useful when it rained the following day, saving us the trouble of purchasing or searching for one. The spa is remarkable, offering a beautiful view and comfortable lounge chairs. The steam room has a delightful lavender scent, and they supply all necessary toiletries for showering or bathing. The pool is pleasantly warm and also offers a lovely view. I thoroughly enjoyed my stay here, so much so that I returned for another visit. I will gladly recommend it to anyone and anticipate returning again soon.

Reviewed on 22 Jul 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was £1,163, price is now £956 per person
£956
per person
7 Sept - 11 Sept
found 13 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (135 reviews)

Chicago Marriott Southwest at Burr Ridge

Chicago Marriott Southwest at Burr Ridge

4 out of 5
Price was £1,628, price is now £1,357 per person
£1,357
per person
8 Oct - 15 Oct
found 17 hours ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)

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

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 £154 per night from 10 Aug to 11 Aug
£154
10 Aug - 11 Aug
includes taxes & fees
Congress Plaza 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
The price is £164 per night from 20 Aug to 21 Aug
£164
20 Aug - 21 Aug
includes taxes & fees
Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
The price is £140 per night from 9 Aug to 10 Aug
£140
9 Aug - 10 Aug
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
See all 2,405 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 £952. 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

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% 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

£31
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.