Chicago Kid friendly Holidays

At Expedia, it’s super-easy to find family-friendly holidays in Chicago in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.

Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Chicago family getaways start at £642. Prices and availability are subject to change and additional terms may apply.

All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Chicago and book the whole package in just a few clicks.

Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.

To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Chicago by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.

Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Chicago family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.

Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.

Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Chicago in no time.