Kid friendly Vacations in Illinois 2026

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Flight and Kid friendly hotel deals in Illinois

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

Warwick Allerton - Chicago

Downtown Chicago

CA $937

per person

Nov 1 - Nov 6

found 17 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

8.6/10 Excellent! (3,012 reviews)

Omni Chicago Hotel

Downtown Chicago

CA $1,398

per person

Oct 2 - Oct 5

found 20 hours ago

Roundtrip flight included

Buffalo (BUF) to Chicago (ORD)

9.2/10 Wonderful! (2,009 reviews)

Room was super nice and clean. Staff were very kind and always helpful. 10/10 experience!

Reviewed on Aug 31, 2026

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

CA $1,190

per person

Oct 1 - Oct 4

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very good! (2,993 reviews)

The location of the hotel is superb to walk around downtown, it's close to many attractions. It's a well maintained place, staff was very helpful and kind. The breakfast is overall good, however the elevators get very busy at times and the breakfast can be crowded too. But if given the chance, I will stay here again!

Reviewed on Aug 31, 2026

Sheraton Grand Chicago Riverwalk

Downtown Chicago

CA $2,192

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

8.6/10 Excellent! (1,829 reviews)

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

CA $1,970

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

8.6/10 Excellent! (2,081 reviews)

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3 Night Kid friendly holidays in Illinois

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

Hilton Chicago

Downtown Chicago

CA $1,029

per person

Oct 12 - Oct 15

found 1 day ago

Roundtrip flight included

Detroit (DTT) to Chicago (ORD)

8.6/10 Excellent! (3,103 reviews)

We stayed for one night at this beautiful and historic hotel. We enjoyed walking through the lobby looking at the history setup they had. The rooms were clean, the view from our room was amazing. We had a lake view + a view of the Buckingham Fountain. The staff was super helpful they were posted throughout the lobby floor ready to help and direct you to your destination. We had the breakfast buffet and the food was great, they had a good variety of breakfast food.

Reviewed on Aug 31, 2026

The Royal Sonesta Chicago Downtown

Downtown Chicago

CA $1,053

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Chicago (ORD)

9.4/10 Exceptional! (3,592 reviews)

Perfect location, within walking distance of so many shops and restaurants. Beautiful view from the river view rooms. Staff are so helpful with unloading and loading your vehicle and getting your luggage up to your room. Valet is easy and convenient.

Reviewed on Aug 31, 2026

Omni Chicago Hotel

Downtown Chicago

CA $1,398

per person

Oct 2 - Oct 5

found 20 hours ago

Roundtrip flight included

Buffalo (BUF) to Chicago (ORD)

9.2/10 Wonderful! (2,009 reviews)

Room was super nice and clean. Staff were very kind and always helpful. 10/10 experience!

Reviewed on Aug 31, 2026

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4 Night Kid friendly holidays in Illinois

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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

CA $1,313

per person

Oct 1 - Oct 5

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (4,474 reviews)

While I have used Hilton Hotels quite consistently especially in big cities and have had good experiences overall, I was very disappointed with our experience at this location. I spent 2 days asking for refills of the toiletries that did not come until the 3rd time I asked. Upon check in the staff have always reviewed all of the amenities available. This staff did not.

Reviewed on Aug 31, 2026

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

CA $1,393

per person

Oct 1 - Oct 5

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (1,552 reviews)

The staff we

Reviewed on Aug 31, 2026

Omni Chicago Hotel

Downtown Chicago

CA $1,836

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.2/10 Wonderful! (2,009 reviews)

Room was super nice and clean. Staff were very kind and always helpful. 10/10 experience!

Reviewed on Aug 31, 2026

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

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

Are there cheap family vacations to Illinois?

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 Illinois 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 Illinois?

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

Can I find luxury family vacations in Illinois?

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

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 Illinois 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 Illinois

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

511 North Columbus Drive Chicago IL

10 min drive from Wrigley Field

CA $201

CA $315 total

Sep 10 - Sep 11

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...

8.2/10 Very good! (2,981 reviews)

"The location of the hotel is superb to walk around downtown, it's close to many attractions. It's a well maintained place, staff was very helpful and kind. The breakfast is overall good, however the elevators get very busy at times and the breakfast can be crowded too. But if given the chance, I ..."

Reviewed on Aug 31, 2026

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

12 min drive from Wrigley Field

CA $253

CA $342 total

Sep 7 - Sep 8

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

10 min drive from Wrigley Field

CA $212

CA $252 total

Sep 7 - Sep 8

includes taxes & fees

Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...

8.6/10 Excellent! (6,013 reviews)

"Upon checking in around 10:00 pm the check in attendant was extremely non committed to explaining the layout/ where the amenities were located and what was available. When I asked a couple of questions, his responses were 1 word answers. This was the first time at this hotel for my husband and I. ..."

Reviewed on Aug 31, 2026

See all 10,380 properties in Illinois

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.