Southmoor Holidays

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Close to the sites we were going to and the price was reasonable.

Reviewed on 10 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Gorgeous room with a breathtaking view!

Reviewed on 10 Jul 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
per person
5 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
No reviews
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on 12 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on 7 Jul 2025

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

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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 €178 per night from 4 Aug to 5 Aug
€178
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on 10 Jul 2025

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
Fully refundable
The price is €148 per night from 10 Aug to 11 Aug
€148
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,232 reviews)
"Our stay was great! Everyone was super helpful and nice!"

Reviewed on 9 Jul 2025

Crowne Plaza Chicago West Loop by IHG
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €129 per night from 4 Aug to 5 Aug
€129
4 Aug - 5 Aug
includes taxes & fees
7/10 Good! (2,229 reviews)
"This hotel is old and needs updated. The ac is a window unit and the heater was a standalone in the room. It felt almost like and old New York City apartment. It was fairly clean however. The price was very affordable and it was only a block from the subway. The staff was excellent. The woman who ..."

Reviewed on 9 Jul 2025

Travelodge by Wyndham Downtown Chicago
See all 2,161 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.

Frequently asked questions

How much does a Southmoor holiday package cost?
Less than you might think --- from as low as €934, as a matter of fact! By combining hotels, flights and car rentals into a custom-made package, your getaway to Southmoor is just a few clicks away.
How do I get a cheap travel package to Southmoor?
Our Southmoor holiday packages promise plenty of savings for the savvy globetrotter. For the best deals, simply bundle your hotel, flights and tours into an affordable package. But low prices are just the beginning of your next awesome adventure. When you book with Expedia, you'll have more than 550 airlines and 1,000,000 hotels across the globe to pick from. Whatever your budget or style, there's a holiday package with your name on it.
Where should I stay in Southmoor?
With fascinating attractions such as Orland Square and Centennial Park Aquatic Centre in this neighbourhood, look for a hotel situated near them. University Of Chicago Medicine is another sight in Southmoor that draws the crowds.
How far in advance should I book my Southmoor holiday?
You'll be rewarded with the biggest variety at the lowest prices by booking your holiday to Southmoor nice and early. Air carriers generally sell flight tickets anywhere up to a year in advance, so secure your spot ASAP. Having said that, Expedia is dedicated to giving you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Southmoor travel package include?
Travel packages include rental cars, hotels and flights, but you can mix and match them to create your dream Southmoor trip. You can also add on fun stuff like tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Southmoor travel package?
You'll score big savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one spot just makes things easier. So why waste your time or money? Whether you're organising a fancy romantic getaway or a low-cost family break, explore our package deals today.
Can I choose my airline with a Southmoor Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just choose the carrier that suits you and put together your ideal Southmoor holiday.
If I'm not able to travel, can I cancel my Southmoor holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Southmoor holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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(125 reviews)

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

Navy Pier
Magnificent Mile - River North showing street scenes, signage and night scenes

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

River tour boat in Chicago

Architecture River Tour

€41
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€38
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.