Chicago, Illinois
Windy, charming perfection in the Midwest.
- More about your Oliver Guide: Cynthia Pillsbury
- Trip type: Family, City
- Activity level: easy
- Ideal length of trip: 3 days with kids
to & from
From any major city fly into Midway or O’Hare. No need to have a car; uber or walk everywhere!
Where to Stay
Chicago Athletic Association (CAA): built in 1893 and recently restored, is a perfect place to call home whether you are with your kids, friends, husband or alone! The location is across from Millennium Park which is central and provides a great view.