Southmoor Holidays from £1,172

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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.
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was £1,476, price is now £1,172 per person
£1,172
per person
10 Jun - 15 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (3,910 reviews)
I would stay here again. Great hotel!

Reviewed on 21 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,623, price is now £1,176 per person
£1,176
per person
26 May - 30 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!

Reviewed on 20 Apr 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,476, price is now £1,909 per person
£1,909
per person
11 Jun - 18 Jun
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,137 reviews)
Great hotel! Very central location, helpful staff. The speak easy was a great surprise

Reviewed on 20 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was £1,625, price is now £1,275 per person
£1,275
per person
26 May - 30 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,417 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 14 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,733, price is now £1,359 per person
£1,359
per person
26 May - 30 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
10/10 highly recommend

Reviewed on 21 Apr 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

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 £100 per night from 26 Apr to 27 Apr
£100
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,164 reviews)
The room shown in the picture is not the one they put me on

Reviewed on 21 Apr 2026

Congress Plaza Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £110 per night from 28 Apr to 29 Apr
£110
28 Apr - 29 Apr
includes taxes & fees
8.8/10 Excellent! (3,454 reviews)
ótima localização, equipe super disponível para ajudar e quarto limpo!

Reviewed on 22 Apr 2026

Club Quarters Hotel, Central Loop, 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 £184 per night from 8 May to 9 May
£184
8 May - 9 May
includes taxes & fees
8.6/10 Excellent! (2,406 reviews)
We love the Palmer House! This is our “go to” hotel when we travel to Chicago. It is close to theaters, concert halls, Michigan Ave with museums, restaurants, parks, etc. The hotel lobby is incredible! A great place to relax, have a beverage, people watch, and enjoy. The room we recently stayed in ...

Reviewed on 20 Apr 2026

Palmer House a Hilton Hotel
See all 2,516 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 £1,172. 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

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
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
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

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
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
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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.