West Side Kid friendly Holidays
Book a Kid friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Kid friendly hotel deals in West Side
Trump International Hotel & Tower Chicago
Reviewed on 2 Oct 2026
5* Kid friendly holidays in West Side
Trump International Hotel & Tower Chicago
Reviewed on 2 Oct 2026
Park Hyatt Chicago
Reviewed on 1 Oct 2026
3 Night Kid friendly holidays in West Side
Trump International Hotel & Tower Chicago
Reviewed on 2 Oct 2026
4 Night Kid friendly holidays in West Side
Trump International Hotel & Tower Chicago
Reviewed on 2 Oct 2026
FAQs: family holidays in West Side
How can I find the best family-friendly holidays in West Side?
At Expedia, it’s super-easy to find family-friendly holidays in West Side 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.
Are there any cheap West Side family holidays?
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, West Side family getaways start at £1,000. Prices and availability are subject to change and additional terms may apply.
Can I book an all-inclusive West Side family holiday package?
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 West Side and book the whole package in just a few clicks.
How can I book the best family activity holiday in West Side?
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.
Can I find luxury family holidays in West Side?
To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in West Side by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.
How can I search for West Side family holiday deals?
Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available West Side 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.
Can I book a West Side family vacation package with free cancellation and/or flexible dates?
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.
Why should I book my West Side family trip with Expedia?
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 West Side in no time.
Things to do
Skydeck Chicago at Willis Tower
Top Kid friendly Holiday Destinations
- Family Friendly Holidays in Barcelona
- Family Friendly Holidays in France
- Family Friendly Holidays in Greece
- Family Friendly Holidays in Ibiza
- Family Friendly Holidays in Ireland
- Family Friendly Holidays in Italy
- Family Friendly Holidays in Majorca
- Family Friendly Holidays in Malta
- Family Friendly Holidays in Menorca
- Family Friendly Holidays in Morocco
- Family Friendly Holidays in New Zealand
- Family Friendly Holidays in Portugal
- Family Friendly Holidays in Scotland
- Family Friendly Holidays in South Africa
- Family Friendly Holidays in Spain
- Family Friendly Holidays in the Canary Islands
- Family Friendly Holidays in the United Kingdom
- Family Friendly Holidays in Turkey
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
