Title: Kid friendly Vacations in Far Southeast Side 2025/2026 | Expedia.ca

  

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# Far Southeast Side Kid friendly Vacations

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## Room 1

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ChildrenAges 2 to 17

InfantsYounger than 2

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## Flight and Kid friendly hotel deals in Far Southeast Side

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

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $574

per person

Nov 22 - Nov 25

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfj_H8sTtSgiRzalTtv_6L0cdi-1i1kqFUAD9cwgwKpm38)

![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Michigan Avenue Chicago

Downtown Chicago

CA $850

per person

Dec 23 - Dec 27

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (1,046 reviews)

One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=rF3q3WsoxfZMM53Mx3365SgugAqfwx0tj5VFs0qWrDq5kfW0nTNalGQqe5bzKopC)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,336

per person

Dec 23 - Dec 27

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Everything was great

Reviewed on Oct 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=2U0YZgHH9wKpNZTA6CIVtU9kV83YW8odwRLu5lzEoK3K0DaPJ3WCSUlZhna6-z_N)

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $583

per person

Nov 22 - Nov 25

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.

Reviewed on Oct 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfj0j9jKepHYLfpOkR_cQTlCfFTJdyNSWrM_uAiX7QYvfI)

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $584

per person

Nov 22 - Nov 25

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (698 reviews)

Property was as it was shown in the pictures. Clean and spacious. Also very easy walk to lots of restaurants and other tourist spots. Would stay again.

Reviewed on Oct 13, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfj0j9jKepHYLfpOkR_cQTlCc-Nv6pVgu7xxdd1gbOVMX6)

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Kid friendly holidays in Far Southeast Side

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

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,092

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.

Reviewed on Oct 14, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=OWBfzzOkUIZbu4Q2F5nRpAE6WsJVnjT-XXNgNCzfZmYdflko5q-n1DNWrityKppx)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,336

per person

Dec 23 - Dec 27

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Everything was great

Reviewed on Oct 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=2U0YZgHH9wKpNZTA6CIVtU9kV83YW8odwRLu5lzEoK3K0DaPJ3WCSUlZhna6-z_N)

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,535

per person

Nov 28 - Dec 1

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining.

Reviewed on Oct 14, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=t-s0udwzxCZ1aB60bCslRDxhOTakJetRudN6uKpjEFXlFwIz5QuIQopknIOb5Khk)

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Kid friendly holidays in Far Southeast Side

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

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $574

per person

Nov 22 - Nov 25

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfj_H8sTtSgiRzalTtv_6L0cdi-1i1kqFUAD9cwgwKpm38)

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,399

per person

Nov 28 - Dec 1

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.

Reviewed on Oct 14, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=t-s0udwzxCZ1aB60bCslRLjaye6s8iA4Hze3sPwD81U24TFgG23jr7ra2fCVJY6e)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,155

per person

Nov 13 - Nov 16

found 6 hours ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Everything was great

Reviewed on Oct 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-16/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=P4s7Hbaa8Nha_LtxlR1gczO0Oxl6QCDNf9k2zUQIks9EsUahAce6b7oqhpicX5AI)

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Kid friendly holidays in Far Southeast Side

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

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $715

per person

Dec 23 - Dec 27

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

Food price was high but everything was fine

Reviewed on Oct 4, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365SgugAqfwx0tj5VFs0qWrDqFQgyNO6MllzSqK4Ijrj0E)

![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Michigan Avenue Chicago

Downtown Chicago

CA $850

per person

Dec 23 - Dec 27

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (1,046 reviews)

One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365SgugAqfwx0tj5VFs0qWrDq5kfW0nTNalGQqe5bzKopC)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,336

per person

Dec 23 - Dec 27

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Everything was great

Reviewed on Oct 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=2U0YZgHH9wKpNZTA6CIVtU9kV83YW8odwRLu5lzEoK3K0DaPJ3WCSUlZhna6-z_N)

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

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

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

Whether it's luxurious or cheap, family vacations in Far Southeast 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 Far Southeast Side.

#### Are there cheap family vacations to Far Southeast 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 Far Southeast 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 Far Southeast Side?

Yes, you'll find plenty of all-inclusive family vacation packages for Far Southeast 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 Far Southeast 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 Far Southeast Side or something a bit more relaxed.

#### Can I find luxury family vacations in Far Southeast Side?

If you're looking for a luxury family vacation to Far Southeast 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 Far Southeast 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 Far Southeast 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.

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## More Vacations Ideas

[Flights to Far Southeast Side](https://expedia.ca/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[Far Southeast Side Hotels](https://expedia.ca/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[Far Southeast Side Vacation Rentals](https://expedia.ca/Far-Southeast-Side-Vacation-Rentals.d553248635976475411.Travel-Guide-VacationRentals)[Far Southeast Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southeast-Side.d553248635976475411.Car-Rental-Guide)[Far Southeast Side Vacations](https://expedia.ca/Far-Southeast-Side.d553248635976475411.Destination-Travel-Guides)

\* 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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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)