Chicago is one of those cities I think is so underrated for a family trip, and where you stay ends up shaping the whole visit more than people expect.
We based ourselves at the Four Seasons Hotel Chicago for a long weekend, and it still remains solidly on my list of go-to family recommendations for the city — with a couple of honest caveats I'll get into.
Quick Facts
Location: Situated right along the magnificent mile and just steps from Lake Michigan and Oak Street Beach.
Best for: Families who want a walkable, upscale home base with real kid amenities
Kids programming : an unsupervised kids' playroom, indoor pool, and complimentary weekend kids buffets
Room we'd book again: City-View Executive Suite
The Location Does a Lot of Work
You're in the Gold Coast, essentially on top of the Magnificent Mile, with the lake, Oak Street Beach, and Michigan Avenue shopping all within an easy walk. For a family trip where you don't want to be white-knuckling rideshares with tired kids at the end of a long day, that matters more than almost any other amenity on the property. We used it as a base and walked to most of what we did.
Family Amenities That Actually Deliver
This is where the hotel earns its spot on my recommend list.
The pool: one of the better hotel pools we've used with kids — and I mean that as a compliment even though (or maybe because) it was full of kids the whole time we were there. That's a good sign, not a bad one, at a family-friendly property.
Kids' playroom: Unsupervised, which is a real perk — it gives families a space to let kids play and decompress without needing to book a sitter or a supervised session every time.
Weekend kids' buffet: Complimentary, and a small detail that makes a real difference on a trip — we enjoyed cocktails while the kids had dinner
The Room: City-View Executive Suite
We booked the City-View Executive Suite and it was the right call — a separate sleeping space for the kids, while we stayed up with a skyline view that made the suite feel like an occasion rather than just a place to sleep.
The One Honest Caveat
The property is older than some of its newer Chicago competitors, and it shows in a few corners — nothing that affected our stay in a meaningful way, but worth knowing going in so it doesn't surprise you. We loved our space and the service was exactly what you'd expect from a Four Seasons, but don't go in expecting a freshly built hotel. Go in expecting a well-run, well-located classic that could use a touch-up in spots.
Why We'd Book It Again
Between the location, the pool, and the playroom, this hit the specific mix that makes a family hotel actually work vs just look good in photos. It's an easy recommendation for families who want a walkable Chicago base without sacrificing the kid-specific amenities that make a trip smoother.
Planning a Chicago trip?
Here is our Weekend in Chicago family guide
and booking your stay through us - as your Four Seasons Preferred Partner - unlocks perks like a room upgrade when available, daily breakfast, and a hotel credit that you won't get booking direct.
