Ultimate Travel Guide for Chicago Families

Regardless of the time of the year, we’re always dreaming of our next vacation. We know making travel plans has been difficult due to the COVID-19 pandemic. Anyone else cancel their vacations at least two or three times last year? But in 2021, we’re seeing more hope to finally fit in that family vacation.

That’s why we decided to assemble this guide to help you plan your next out-of-town family adventure. Whether you’re heading out on a road trip or leaving on a jet plane, we’ve got you covered with the latest family travel content. Below, you’ll find travel tips, staycation ideas in Chicagoland, road trips worth the drive and more family vacations.

Be sure to bookmark this handy guide, because we’ll be adding more kid-friendly travel ideas. We also made sure to include socially-distant options and even some fun virtual family vacations as we try to slow down the spread of COVID-19. Safe travels!

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As much as we want to vacation and create new family memories, planning a trip with kids can be quite stressful! You have to make sure everyone is packed and that a travel itinerary is planned out before you arrive.

We want to help you lighten the load with some quick and easy family travel tips. Make your life easier with this vacation checklist for kids, road trip snacks to make in advance and more.

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Vacation Checklist for Kids to Help Them Pack for a Trip

Have them learn how to pack like a pro.


Sometimes you don’t have to travel that far to enjoy a nice family vacation. Staycations are a great idea if you want to spend more time in the city or out in the suburbs. We have plenty of kid-approved activities, hotels and attractions to make your family happy that you stayed in Chicagoland.

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Hit the road! Family road trips never get old, and we’re so lucky to have some great Midwest destinations near Chicago. There’s so much you can see with your kids when driving only a few hours away. We have European-style small towns, dinosaur attractions, national parks and other fun ideas below.

Incredible Midwest Destinations to Visit with Kids in 2024

Need a break? Jump in the car and hit the road!

Midwest Food Trails Worth the Trip

Don't read on an empty stomach!

Family-Friendly Vacation Rentals Worth the Drive

Rent out one of these awesome vacation pads.

Best Places to See with Kids in Illinois

Enjoy a bucket list for Illinoisans of all ages!

Family-Friendly Route 66 Stops to Make in Illinois

Experience a bit of this Americana icon.


Perhaps you’re ready to plan a bigger trip with your family in 2021. Some popular destinations are Disney World, Wisconsin Dells and Key Largo. Find some of our travel guides that include family-approved recommendations for hotels, restaurants and attractions.

Family Travel Guide to Wisconsin Dells: What’s New in 2024

Uncover Wisconsin Dells’ family-friendly attractions and activities, perfect for creating the most unforgettable vacation.
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