Popular Family Vacation Cities in Fall

Take a trip to one of the top destinations in the US for family vacations in the fall.


Crown Fountain-Chicago

Recently voted one of the top US cities everyone in their 20’s should visit, Chicago offers lots of family-friendly seasonal fun, too.

September in Chicago is known for their abundance of street festivals ranging from beer festivals to antique furniture art and design festivals. Check out a street festival during your visit for fun, entertainment, and grab a unique locally made souvenir.

Take advantage of the seasonally crisp, cool air and plan a family biking tour of the city for a fun, alternative way to get to know the city.


Fall is the most beautiful time of year in Boston and there are lots of family-friendly things to do in the fall.

See the best New England fall foliage on a guided fall foliage tour or check out the interactive fall foliage map to see where in New England you can see foliage at its peak.

Nowhere else does Halloween like Salem. Join in on the bewitching fun in Salem by visiting the Salem Witch Museum and set aside some time to poke around the shops and join in on the festivities around town.

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