Central Chicago Kid friendly Vacations

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Flight and Kid friendly hotel deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $762
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,518
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!

Reviewed on Aug 12, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,873
per person
Nov 5 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on Aug 10, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,379
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,412
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
I’m okay on them

Reviewed on Aug 11, 2026

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5* Kid friendly holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,184
per person
Nov 6 - Nov 8
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Simply the Best, just like 45/47!

Reviewed on Aug 12, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,873
per person
Nov 5 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on Aug 10, 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
CA $2,749
per person
Oct 2 - Oct 6
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
We had a terrific weekend stay! The staff was so friendly and the room was wonderful with a very comfortable bed. Location is very convenient, as well.

Reviewed on Aug 10, 2026

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3 Night Kid friendly holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,072
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!

Reviewed on Aug 12, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,873
per person
Nov 5 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on Aug 10, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,234
per person
Oct 16 - Oct 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
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4 Night Kid friendly holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
CA $997
per person
Oct 22 - Oct 26
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
Great service

Reviewed on Aug 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,518
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!

Reviewed on Aug 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,416
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
I’m okay on them

Reviewed on Aug 11, 2026

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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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Central Chicago

More vacations you might like

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