Title: Kid friendly Vacations in Central Chicago 2025/2026 | Expedia.ca

  

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# Central Chicago 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 Central Chicago

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 13 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-7lgW89xzilfjyc278bAoffCvb7VzePwaQlahYjoAWNHaBUPfOsjzwmT)

![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 17 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=rF3q3WsoxfZMM53Mx3365a-BKXswNKhBBkAtb-ba-LM9uiOYPxeAPiIK4EUwtp1c)

![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Art Villa

West Town

CA $1,148

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-16/2025-12-20/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=OWBfzzOkUIZbu4Q2F5nRpDCeuzHvJ6bt56UVTIqKKrJwNDyPm6tx29y5QhHE7mXS)

![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 17 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=2U0YZgHH9wKpNZTA6CIVtWWDXQGmNxr2PPm4Wfmd0dPb7yZ2y4qeCCJ-4Vra4Nd0)

![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 13 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-7lgW89xzilfj9LoBAT4yBfpEoUOUoYnyTyokG0YfqKi_tUAmqe8pRKo)

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[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 Central Chicago

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 22 hours 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=OWBfzzOkUIZbu4Q2F5nRpPw_lMq-sk0S3c7YGBh0dQbAMOQRUJax_gmDLHhRcdlO)

![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Art Villa

West Town

CA $1,148

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-16/2025-12-20/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=50&dealMarker=OWBfzzOkUIZbu4Q2F5nRpDCeuzHvJ6bt56UVTIqKKrJwNDyPm6tx29y5QhHE7mXS)

![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 17 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=2U0YZgHH9wKpNZTA6CIVtWWDXQGmNxr2PPm4Wfmd0dPb7yZ2y4qeCCJ-4Vra4Nd0)

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[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 Central Chicago

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 13 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-7lgW89xzilfjyc278bAoffCvb7VzePwaQlahYjoAWNHaBUPfOsjzwmT)

![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 2 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-s0udwzxCZ1aB60bCslRG-V_OMA0Qednm3Pteoz4u1k_La5wKsItIW_vkhaUAwi)

![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 $1,281

per person

Nov 28 - Dec 1

found 4 hours ago

Roundtrip non-stop flight included

Montreal (YUL) 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/2025-11-28/2025-12-01/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=Vk5nqoznAJ9PCpHTBklWqNyawQA3a2EgikHSTevztn8VPaZBE6cLKGG_CmQF36cC)

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[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 Central Chicago

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

![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 17 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=rF3q3WsoxfZMM53Mx3365a-BKXswNKhBBkAtb-ba-LM9uiOYPxeAPiIK4EUwtp1c)

![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Art Villa

West Town

CA $1,148

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-16/2025-12-20/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&dealMarker=OWBfzzOkUIZbu4Q2F5nRpDCeuzHvJ6bt56UVTIqKKrJwNDyPm6tx29y5QhHE7mXS)

![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 17 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=2U0YZgHH9wKpNZTA6CIVtWWDXQGmNxr2PPm4Wfmd0dPb7yZ2y4qeCCJ-4Vra4Nd0)

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[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 Central Chicago with Expedia

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

Whether it's luxurious or cheap, family vacations in Central Chicago 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 Central Chicago.

#### Are there cheap family vacations to Central Chicago?

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 Central Chicago 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 Central Chicago?

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

#### Can I find luxury family vacations in Central Chicago?

If you're looking for a luxury family vacation to Central Chicago, 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 Central Chicago.

#### 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 Central Chicago 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 Central Chicago](https://expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights)[Central Chicago Hotels](https://expedia.ca/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)[Central Chicago Vacation Rentals](https://expedia.ca/Central-Chicago-Vacation-Rentals.d553248635976475413.Travel-Guide-VacationRentals)[Central Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Central-Chicago.d553248635976475413.Car-Rental-Guide)[Central Chicago Vacations](https://expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides)[Things to do in Central Chicago](https://expedia.ca/Things-To-Do-In-Central-Chicago.d553248635976475413.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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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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)