Title: Luxury Vacations in South Side 2026 | Expedia.ca

![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# South Side Luxury Vacations

## Book a Hotel + Flight or Car together to unlock savings

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Plan, book, and manage your trip all in one place

## Flight and Luxury hotel deals in South Side

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

![Hyatt Regency McCormick Place Chicago   ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/bc1f3373_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency McCormick Place Chicago 

Near South Side

CA $1,529

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.2/10 Wonderful! (1,064 reviews)

Clean toom beautiful views

Reviewed on Mar 3, 2026

![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wheeler Mansion

Near South Side

CA $1,956

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

Don't see what you're looking for?

See all available trips from Columbus to South Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Luxury holidays in South Side

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

![Hyatt Regency McCormick Place Chicago   ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/bc1f3373_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency McCormick Place Chicago 

Near South Side

CA $1,529

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.2/10 Wonderful! (1,064 reviews)

Clean toom beautiful views

Reviewed on Mar 3, 2026

![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wheeler Mansion

Near South Side

CA $1,956

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

Don't see what you're looking for?

See all available trips from Columbus to South Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Luxury holidays in South Side

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

![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Best Western Grant Park Hotel

Downtown Chicago

CA $628

per person

Apr 13 - Apr 17

found 23 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

8.2/10 Very Good! (2,688 reviews)

Everything was fantastic.

Reviewed on Mar 10, 2026

![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chinatown Hotel Chicago

Chinatown

CA $740

per person

May 26 - May 30

found 6 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

5.4/10 (1,000 reviews)

Great for roding the cta

Reviewed on Jan 13, 2026

![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wheeler Mansion

Near South Side

CA $2,296

per person

May 6 - May 10

found 22 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

Don't see what you're looking for?

See all available trips from Columbus to South Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Plan the perfect luxury South Side vacation with Expedia

####  What are some benefits when booking luxury South Side vacations? 

When you book a luxury South Side vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. 
  
####  How can I find all-inclusive luxury vacations in South Side? 

If you're looking for something luxurious in South Side, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. 

####  Can I book a cheap luxury vacation? 

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $628, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 4\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. 

####  Are there luxury spa vacations? 

Yes, luxury spa vacations are available and quite popular in South Side. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. 

####  What should I look for in a luxury family vacation in South Side? 

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout South Side.

####  Can I book last-minute luxury vacations? 

Yes, last-minute bookings are often available in South Side. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

####  What can help me find the best luxury vacation deals in South Side? 

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of South Side or travelling to more obscure destinations altogether can often lead to lower prices.

####  Can I book a luxury vacation that is fully refundable? 

Yes, fully refundable reservations are sometimes available on luxury vacation packages in South Side. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. 

####  Why should I book my luxury vacation with Expedia? 

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

## Luxury Hotels in South Side

![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

- 11 min drive from University of Chicago

Book a stay at this luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...

[](https://expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information)

![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

- 14 min drive from University of Chicago

Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...

8.2/10 Very Good! (2,692 reviews)

The staff was wonderful today

Reviewed on Mar 13, 2026

[](https://expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information)

![Hyatt Regency McCormick Place Chicago   ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/bc1f3373_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Regency McCormick Place Chicago 

2233 S Martin Luther King Dr Chicago IL

- 11 min drive from University of Chicago

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...

9.2/10 Wonderful! (1,063 reviews)

Clean toom beautiful views

Reviewed on Mar 3, 2026

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information)

[See all 469 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635074842823)

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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## More Vacations Ideas

[Flights to South Side

](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[

South Side Hotels

](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[

South Side Vacation Rentals

](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[

South Side Car Rentals

](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[

South Side Vacations

](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)[

Things to do in South Side

](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)

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

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