Title: Kid friendly 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 Kid friendly Vacations

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## Flight and Kid friendly 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/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency McCormick Place Chicago 

Near South Side

CA $1,019

per person

Mar 14 - Mar 17

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,018 reviews)

The room and staff were great

Reviewed on Jan 6, 2026

![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wheeler Mansion

Near South Side

CA $2,544

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Marriott Marquis Chicago

Near South Side

CA $2,199

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9/10 Wonderful! (1,000 reviews)

Our room was beautiful!!

Reviewed on Jan 21, 2026

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/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Kid friendly 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/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency McCormick Place Chicago 

Near South Side

CA $1,019

per person

Mar 14 - Mar 17

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,018 reviews)

The room and staff were great

Reviewed on Jan 6, 2026

![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wheeler Mansion

Near South Side

CA $1,561

per person

Apr 22 - Apr 25

found 1 day 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/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Kid friendly 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 $566

per person

Apr 12 - Apr 16

found 17 hours ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

8.2/10 Very Good! (2,619 reviews)

Room was clean and well maintained, good view and comfortable. They were able to accommodate and check me in early. However, as someone who is a light sleeper, I had a loud neighbor next door :( which made it hard to fully relax. I contacted the front desk and they were able to send security up but the noise continued. Overall, it’s a very nice and comfortable hotel.

Reviewed on Feb 4, 2026

![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Jaslin Hotel

Chinatown

CA $748

per person

Apr 2 - Apr 6

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

8.8/10 Excellent! (1,173 reviews)

Great service and clean roomd

Reviewed on Jan 23, 2026

![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chinatown Hotel Chicago

Chinatown

CA $636

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

5.4/10 (1,001 reviews)

Great for roding the cta

Reviewed on Jan 13, 2026

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/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Plan the perfect family-friendly vacation in South Side with Expedia

####  What are some benefits of booking a family-friendly vacation? 

Whether it's luxurious or cheap, family vacations in South Side are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships. 
  
####  How can I find the best family-friendly vacations? 

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to South Side. 

####  Are there cheap family vacations to South Side? 

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard. 

####  When should I book family-friendly vacation packages? 

The right time to book family-friendly vacation packages in South Side depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example. 

####  Can I book an all-inclusive family vacation in South Side? 

Yes, you'll find plenty of all-inclusive family vacation packages for South Side. To see what's available, just select the all-inclusive filter on your search.

####  How can I book the best family activity vacation? 

If you're looking to make the most out of the available activities in South Side, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in South Side or something a bit more relaxed.

####  Can I find luxury family vacations in South Side? 

If you're looking for a luxury family vacation to South Side, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line. 

####  How can I search for family vacation deals? 

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in South Side. 

####  Can I book a family vacation package that is fully refundable? 

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in South Side are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

####  Why should I book my family trip with Expedia? 

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.

## Kid friendly Hotels in South Side

![Hyatt Regency McCormick Place Chicago   ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_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 ...

9/10 Wonderful! (1,064 reviews)

Very nice Hotel. Nice room and view!! The staff were friendly. We will be back to stay at this Hotel.

Reviewed on Jan 31, 2026

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

8/10 Very Good! (2,666 reviews)

The room was clean however the sink was clogged and the heat didnt work properly

Reviewed on Feb 2, 2026

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

![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Jaslin Hotel

261 West Cermak Rd Chicago IL

- 11 min drive from University of Chicago

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

8.8/10 Excellent! (1,179 reviews)

Great service and clean roomd

Reviewed on Jan 23, 2026

[](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information)

[See all 474 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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