South Deering Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Where to stay in South Deering

Find the best South Deering areas and neighborhoods for the activities you enjoy most. Learn more about South Deering
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 South Deering

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 S$162 per night from 8 Dec to 9 Dec
S$162
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,162 reviews)
"Everyone was super nice and they let us check in when we got there even though it was before check in time. Definitely would stay here again"

Reviewed on 27 Nov,2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$170 per night from 16 Dec to 17 Dec
S$170
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (3,552 reviews)
Great stay!
"Great location! Front desk was very helpful in giving some local recommendations."

Reviewed on 26 Nov,2024

River 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 S$162 per night from 8 Dec to 9 Dec
S$162
includes taxes & fees
8 Dec - 9 Dec
8.4/10 Very Good! (3,252 reviews)
Chicago stay
"This hotel was very clean and the staff were helpful and courteous. I would definitely stay there again. Its conveniently located near most attractions."

Reviewed on 27 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 3,937 properties in South Deering
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 South Deering holiday package cost?
Create unforgettable memories with our South Deering holiday packages, which start from just . Pick the hotels and flights that suit your travel style. Then, add on a few activities or tours to round off your unique adventure.
How do I get a cheap travel package to South Deering?
Bundle your flights and hotels with Expedia to save big on your next exciting adventure. With over 550 partner airlines and 1,000,000 properties across the world, your South Deering holiday package can be tailored exactly to suit your travel style. With all that extra money, why not throw in a few fun experiences and tours? It’s an easy way to unlock even more bargains. That holiday you’ve always dreamed of in South Deering is closer than you thought!
Where should I stay in South Deering?
A holiday in South Deering wouldn’t be complete without seeing Calumet Beach, Calumet Park and Harborside International Golf Centre. Spend your nights close to these popular sights and make sightseeing easy.
How far in advance should I book my South Deering holiday?
Savvy travellers often book as early as possible. You can generally look up international airfares on Expedia up to a year before your flight. If you’re booking last minute, don’t worry. Low prices occasionally appear just weeks prior to departure.
What does an Expedia South Deering travel package include?
Rental cars, flights and hotels, or any combination of them — the choice is all yours! Whether you’re exploring South Deering with the whole family or adventuring solo, there’s a package to suit every style and budget. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking a South Deering travel package?
Discover deals to match your budget with an Expedia package. Flights, hotels, rental cars — we’re a one-stop shop for all of them. You’ll save loads just by combining your bookings. Whether you’re going on a skiing adventure or sipping cocktails on a beach, your perfect getaway is only a few clicks away.
Can I choose my airline with a South Deering Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you’d prefer to fly to South Deering in coach or business class, simply select from the available airline options. Expedia has access to more than 550 partner airlines throughout the world.
If I'm not able to travel, can I cancel my South Deering holiday package?
It’s difficult to predict what tomorrow might bring, so it’s comforting to know that you can change or cancel your South Deering holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

Flyover in Chicago

Flyover in Chicago

S$51
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$65
Per adult
94% of travellers recommend
Architecture River Tour
Private Chicago Scavenger Hunt: Eastside Art Heist

Eastside Chicago The Heist Exploration Game and Tour

S$14
Per adult
Eastside Chicago The Heist Exploration Game and 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.