Chicago With Kids: Everything We Learned
We spent two weeks in Chicago and Wisconsin with two boys — three full days in the city, a week at a basketball camp near Milwaukee, and a final stretch back in Chicago. This page collects everything we wrote from that trip, in the order you’d actually need it.
Start here
The four posts that answer the questions you have first.
3 Days in Chicago With Kids: Our Real Itinerary Hour by hour, what each stop cost, how we got between them, and what we’d change. The river cruise first, then the observation deck — do it in that order.
What Our Chicago Trip Really Cost €6,359.14 for four people over 13 days, broken down by category. Flights were 36% of it. Attractions were 6%.
Where to Stay in Chicago With Kids Three hotels, honestly. Only one I’d book again, and it isn’t the one with the best location.
The Best Time to Visit Chicago With Kids Month by month. We went in July; we’d choose early June or September next time.
The views
Two observation decks, one river. If you only do one of these, make it the cruise.
Shoreline Architecture River Cruise — the best introduction to the city, and the thing to do first.
Skydeck Chicago at Willis Tower — the 103rd floor and The Ledge, the glass box you stand in. $32 adult, $24 child.
360 Chicago and the TILT — the 94th floor, and the one where the gimmick costs $18 extra per person.
Is CityPASS C3 worth it? — we used it for all three above. Here’s the arithmetic.
Free things we actually did
Chicago is unusually generous, and this is the section I’d send a family on a budget straight to.
Millennium Park and the Bean — plus Crown Fountain, where kids can play in the water, and Maggie Daley Park over the bridge.
Lincoln Park Zoo — one of the only free zoos in the United States, open every day of the year, and the best day of our three.
Grant Park and Buckingham Fountain — go after dark.
The Michael Jordan statue at the United Center — free, no ticket needed, and worth the trip if there’s a basketball fan in the family.
Home Alone filming locations — eight spots you can visit. Best in December, for obvious reasons.
Navy Pier — the pier itself is free; the rides are not.
Where we ate
Where to eat in Chicago with kids — the overview, including how we kept the food budget down.
- Giordano’s deep dish — the one meal that’s non-negotiable. Order the moment you sit down; it takes 30–45 minutes to cook.
- Portillo’s — fast, cheap, Chicago.
- Nutella Café on Michigan Avenue — breakfast, with a queue.
- Starbucks Reserve Roastery — five floors, the largest Starbucks in the world, free to walk around.
The money-saving version: we spent more on supermarkets than restaurants — €521.52 against €492.05 across the trip. Whole Foods has a hot bar priced by weight with seating, and with children it’s faster than a restaurant as well as cheaper.
Basketball, and the Milwaukee side
The reason the trip existed, and a niche almost nobody writes about honestly.
Our week at the Milwaukee Bucks summer camp — €645.89 for both boys.
Country Inn & Suites, Brookfield, Wisconsin — where we stayed for the camp week, and the hotel of the trip we’d book again.
Getting there and getting around
Flying United Basic Economy from Barcelona to Chicago — what the fare actually includes, and what it doesn’t, with children.
You don’t need a car in Chicago. Ventra cards for the four of us cost €78.77 for the whole trip. We only rented a car for the Wisconsin week — €196.31 for seven nights, collected from an office we could walk to
What we’d tell a family going for the first time
- Do the river cruise on day one, before anything else. Everything afterwards makes more sense.
- Stay in the Loop or South Loop. Walkability beats hotel facilities when you have kids.
- Don’t build a plan around the Bean. It’s twenty minutes. The park around it is the morning.
- Protect the free day. Lincoln Park Zoo was better than either observation deck.
- Eat one meal a day from a supermarket. It’s the difference between an affordable trip and an expensive one.
- Don’t plan anything for your arrival evening. Coming from Europe, that day isn’t a day.
Chicago With Kids: FAQs
Is Chicago good for a family holiday with kids?
Yes, and it is one of the easier large American cities to visit with children. The downtown attractions are within walking distance of each other, public transport covers the rest so no car is needed, and many of the best things are free, including Millennium Park, Cloud Gate, Crown Fountain, Grant Park and Lincoln Park Zoo. We spent three full days in the city with two boys and did not run out of things to do.
How many days do you need in Chicago with kids?
Three full days covers the main attractions without rushing: an observation deck, the architecture river cruise, Millennium Park and the Bean, Navy Pier and Lincoln Park Zoo, with time for deep dish pizza. A fourth day lets you add the Field Museum or Shedd Aquarium. Do not count your arrival day if you are flying long haul, because you will not use it.
What are the best free things to do in Chicago with kids?
Lincoln Park Zoo, which is free every day of the year, Millennium Park and Cloud Gate, Crown Fountain where children can play in the water in warm weather, Maggie Daley Park with its free play garden and climbing walls, Grant Park and Buckingham Fountain after dark, the Riverwalk, and the Michael Jordan statue at the United Center. Together these could fill two days at no cost.
Do you need a car in Chicago with children?
No. We had no car for our days in Chicago and never needed one. Ventra cards covering public transport for our family of four cost 78.77 euros for the whole trip, and the main downtown attractions are 15 to 25 minutes apart on foot. A car downtown only adds parking costs.
How much does a family trip to Chicago cost?
Our 13 night trip from Barcelona cost 6,359.14 euros for two adults and two children, including flights, hotels, food, attractions and a week of basketball camp in Wisconsin. Flights were the largest single cost at 36 percent of the total, while attractions were only 6 percent, because so much of Chicago is free.
Where should families stay in Chicago?
The Loop or South Loop for a first visit, because you can walk to Millennium Park, Grant Park, the Riverwalk and Michigan Avenue without using transport. River North and Streeterville cost more but have newer rooms and pools. Avoid basing yourself near O’Hare airport unless you have an early flight, as the journey into the city takes around 40 minutes each way.
