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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,202, price is now CA $833 per person
CA $833
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that

Reviewed on Jun 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,919, price is now CA $1,261 per person
CA $1,261
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,014, price is now CA $1,402 per person
CA $1,402
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $3,418, price is now CA $2,419 per person
CA $2,419
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The hotel was wonderful. Everything was extremely clean, the entire staff was very friendly, and the service was exceptional. We had the best experience

Reviewed on Jun 14, 2026

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

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 $191 per night from Jun 29 to Jun 30
CA $191
CA $227 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,269 reviews)
"The stay was great! It’s more of a historic hotel vibe. Spent a lot of time waiting on the elevator only one was working. Room was clean and bed was comfy. Tv in the room is from like the early 2000’s. But we didn’t spend much time in the room do that was oaky. I am always a little disappointed when ..."

Reviewed on Jun 14, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $202 per night from Jun 30 to Jul 1
CA $202
CA $240 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,582 reviews)
"Very nice, loved the breakfast and rooftop bar"

Reviewed on Jun 14, 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Jun 29 to Jun 30
CA $219
CA $260 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,606 reviews)
"The rooms were ugly! Where as the hotel was beautiful! The front desk staff were snotty and acted like y were doing them a favor checking in. However, all other staff were wonderful. I would stay here again, but upgrade room… alot"

Reviewed on Jun 14, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,276 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.
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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 $833. 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.

Stay near popular South Deering attractions

Harborside International Golf Center

Enjoy a round of golf in Chicago at Harborside International Golf Center. Stroll along the lakeside or attend a sporting event in this vibrant area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.