South Suburbs All inclusive Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and All inclusive hotel deals in South Suburbs

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

Swissotel - Chicago

Downtown Chicago
CA $983
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
CA $1,120
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
CA $2,564
per person
Dec 13 - Dec 18
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago
CA $1,159
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,133 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
CA $1,021
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
An amazing location for Chicago and a beautiful hotel

Reviewed on Oct 1, 2026

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5* All inclusive holidays in South Suburbs

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

Nobu Hotel Chicago

Downtown Chicago
CA $1,108
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (936 reviews)
The staff is wonderful!! There’s lots of little perks here that made our stay better (slippers and replenished washcloths before bed, for example). The only thing I’d change is the valet parking - you must wait in the street until a valet is available - there isn’t a covering or lot to pull into while waiting. Overall though, highly recommended and would definitely stay again!!

Reviewed on Oct 1, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $2,435
per person
Nov 16 - Nov 23
found 21 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
CA $2,564
per person
Dec 13 - Dec 18
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

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3 Night All inclusive holidays in South Suburbs

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $882
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,436
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,118
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

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4 Night All inclusive holidays in South Suburbs

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
CA $1,120
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
CA $2,143
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
CA $1,371
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
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Embark on an unforgettable all-inclusive trip to South Suburbs including airfare with Expedia

What are some benefits of booking an all-inclusive vacation?

When you opt for an all-inclusive vacation to South Suburbs, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget.

Can I book all-inclusive packages with airfare and meals?

Yes, all-inclusive vacation packages are readily available for South Suburbs, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 28.

Why should I book South Suburbs vacations that are all inclusive and adults only?

Adults-only stays in South Suburbs are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find.

Can I book all-inclusive packages?

Yes, all-inclusive packages are fairly standard in South Suburbs. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive.

Can I book cheap all-inclusive trips to South Suburbs?

If you're looking to save, you'll find a wide range of prices available, ranging from CA $882. By booking your accommodations and flight together, you may be able to enjoy savings of up to 28. Be sure to sort your search results by price to list the cheapest options first.

What should I look for when booking a 5-star all-inclusive vacation in South Suburbs?

If you've implemented the 5-star filter when searching for your all-inclusive vacation in South Suburbs, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group.

What should I consider when booking South Suburbs vacation packages that are all inclusive for the family?

The most important thing to consider for all-inclusive family vacations to South Suburbs is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying South Suburbs's nightlife.

How can I find the best deals on all-inclusive vacations in South Suburbs?

You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters.

Can I book an all-inclusive package that is fully refundable?

Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify.

Why should I book an all-inclusive vacation with Expedia?

Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.