Southmoor Holidays

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    Packages with flights are ATOL protected

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.
  • Indoor wedding
    Jul 6 - Jul 12

    Swissotel - Chicago + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.0/10 - Wonderful (3,367 reviews)
    "Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
    Reviewed June 6, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,440
    £1,095
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Lobby sitting area
    Jul 6 - Jul 12

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    8.4/10 - Very good (1,959 reviews)
    "Ñ"
    Reviewed June 6, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,514
    £1,124
    per traveller
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Terrace/patio
    Jul 11 - Jul 18

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,526 reviews)
    "Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission."
    Reviewed June 4, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    £1,965
    £1,469
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 12 - Aug 16

    Level Chicago – Old Town + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.0/10 - Wonderful (488 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Return • Manchester (MAN) - Chicago (ORD)
    MAN - ORD • 1 stop ORD - MAN • 1 stop
    £1,904
    £1,430
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Terrace/patio
    Jul 11 - Jul 18

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,882 reviews)
    "We love the pool, cleanliness in the room .Friendly staff"
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    Save 100% on your flight
    £2,676
    £2,033
    per traveller
    found 23 hours ago
    Trump International Hotel & Tower Chicago

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,179 reviews)
"Location was good to train station and grand park but biggest issue we had is no water pressure and it was at best lukewarm. This makes me now want to always check first before booking anything how their water service is. It was terrible and when I checked previous reviews it was one of biggest complaints. ..."

Reviewed on 6 Jun 2026

Congress Plaza Hotel
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 £222 per night from 2 Jul to 3 Jul
£222
2 Jul - 3 Jul
includes taxes & fees
8.6/10 Excellent! (2,477 reviews)
"Check in was horrible. The longest lines you can imagine….face me 250 Hilton points….not useful for me. Property is beautiful if you look closely but it is not well maintained."

Reviewed on 4 Jun 2026

Palmer House a Hilton 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 £140 per night from 1 Jul to 2 Jul
£140
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (2,239 reviews)
"I had an amazing time in Chicago, not one complaint. Everyone was pleasant and my room was clean."

Reviewed on 4 Jun 2026

Crowne Plaza Chicago West Loop by IHG
See all 2,468 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 . 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

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

Wrigley Field
Navy Pier

Navy Pier

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

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
86% 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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£80
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.