South Deering Vacation Packages

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Top Holiday Package Deals in South Deering

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,043, price is now CA $655 per person
CA $655
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
This hotel was lovely. The room was large and smelled divine. Everything was spotless, beds were comfy, location was excellent, staff were friendly and accommodating. Would definitely stay here again. :)

Reviewed on Sep. 4, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,667, price is now CA $1,008 per person
CA $1,008
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!

Reviewed on Sep. 2, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $4,082, price is now CA $2,538 per person
CA $2,538
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $3,378, price is now CA $2,120 per person
CA $2,120
per person
Nov 17 - Nov 23
found 2 days ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

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 showing a city

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

South Deering Hotel Deals

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 CA $204 per night from Sep 16 to Sep 17
CA $204
CA $239 total
Sep 16 - Sep 17
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Sep 22 to Sep 23
CA $252
CA $296 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Sep 22 to Sep 23
CA $230
CA $270 total
Sep 22 - Sep 23
includes taxes & fees
The Wade
See all 4,443 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a South Deering vacation package cost?
Create unforgettable memories with our South Deering vacation packages, which start from just CA $655. 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 vacation 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 vacation you've always dreamed of in South Deering is closer than you thought!
Where should I stay in South Deering?
A vacation in South Deering wouldn't be complete without seeing Calumet Beach, Calumet Park and Harborside International Golf Center. Spend your nights close to these popular sights and make sightseeing easy.
How far in advance should I book my South Deering vacation?
Savvy travelers 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 vacation package?
With a vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in South Deering

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

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy 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
Navy Pier

Navy Pier

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
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

CA $62
per adult
96% 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.