We flew into Chicago from Barcelona with two boys, three days before we had to be in Milwaukee. We had never thought of coming to Chicago, but it came out to be one of the best adventures.
The three days at a glance
Arrival night — landed late, went to the hotel, slept. Plan nothing for this one. Day 1 — Starbucks → Michigan Avenue → Shoreline architecture river cruise → Whole Foods for lunch → Skydeck → Grant Park and Buckingham Fountain after dark Day 2 — Nutella Café → Millennium Park and the Bean → 360 Chicago → Giordano’s → Navy Pier Day 3 — Dunkin’ for breakfast → Lincoln Park Zoo (free) → pick up the rental car → Milwaukee
A few things that shape the whole trip:
- You don’t need a car. We didn’t have one for Chicago and never wanted one. Ventra cards for the four of us came to €78.77 across the whole trip.
- Three of the big attractions came through CityPASS C3 — Skydeck, the architecture cruise and 360 Chicago — €347.74 for two adults and two children in July 2025.
- The best day was the free one. Lincoln Park Zoo is one of the only free zoos in the United States, and it was the day that needed the least planning and delivered the most.
- The order we did it in was right, and it wasn’t planned that way: the river cruise on the first morning, then Skydeck in the afternoon. You see the buildings from the water with someone explaining them, and then you look down on the same buildings from 103 floors up. Do it in that order.
Prices in this post are from July 2025. Ticket prices change; check before you budget.
The arrival night — plan nothing
We flew Barcelona to Chicago with United, in Basic Economy, which is its own story — the hand luggage rules alone are worth reading before you book with two kids. 👉 Flying United Basic Economy from Barcelona to Chicago
We landed late in the evening, went straight to the hotel, and slept. We didn’t see a single thing that night, and I’d do the same again.
This is worth saying because a lot of itineraries quietly pretend the arrival day is a full day. Coming from Europe it isn’t. You land tired, with children who are seven hours out of step, and anything you force into that evening you’ll pay for the next morning. Treat the arrival night as travel, not sightseeing — the three days below are three full days, starting the morning after.
Day 1 — The river first, then the top
The best-sequenced day of the trip, and honestly it happened by accident. You see the buildings from the water with a guide explaining them, and a few hours later you’re looking down on the same buildings from 103 floors up. In that order, Chicago makes sense.
Starbucks Reserve Roastery
We came here around 9 am. Jetlagged, with a sleepless night behind, just a place we needed.
Not really a coffee stop — five floors, the largest Starbucks in the world, pastries at the bottom and a cocktail bar at the top. It’s a free thing to walk around when you’ve run out of plan, and it’s indoors, which makes it the obvious rescue if the weather turns. 👉 Starbucks Reserve Roastery, floor by floor
Michigan Avenue
Then we walked Michigan Avenue. No plan, no tickets — just the walk. The mix of historic and modern along the avenue is the free architecture tour before the paid one, and it’s a gentle way to start a first full day with kids who are still adjusting to the time change.
The Shoreline architecture river cruise
Our second CityPASS attraction, and the one I’d tell anyone to do first in Chicago.
The Michigan Avenue dock is at 401 N. Michigan, right off the avenue you’ve just walked, so it slots in without any travelling. Cruising the river while someone explains what you’re looking at gives you a map in your head for the rest of the trip — after this, the buildings you see from the top of Willis Tower are buildings you can name.
Shoreline runs 60, 75 and 90-minute versions. With younger children the 60-minute is plenty. 👉 Our architecture river cruise with the kids
Lunch at Whole Foods
Not a restaurant — a supermarket. And it’s one of the most useful things I can tell you about eating in downtown Chicago with a family.
Whole Foods has a hot bar and salad bar where you pay by weight, plenty of seating, and it’s a fraction of what four people pay in a sit-down restaurant in the Loop. With kids it also solves the problem restaurants create: nobody waits, everyone picks what they actually want, and you’re back out in half an hour instead of ninety minutes.
We ate this way often on this trip — our grocery spend across the whole holiday came to €521.52 against €492.05 in restaurants, which for a family of four in the US is the difference between a trip that works and one that doesn’t.
Skydeck Chicago, Willis Tower
Our third CityPASS attraction, and the afternoon of Day 1. Allow 1–1.5 hours including the exhibits, the lift and the queue for The Ledge.
The entrance is on the south side of the tower, on Jackson Boulevard — not the main lobby, and it’s the kind of thing that costs you ten minutes if nobody tells you.
Standing on The Ledge, a glass box 1,353 feet up, is the part everyone remembers. It’s genuinely nerve-wracking, and the view runs across the city and into the neighbouring states on a clear day.
One honest caveat about doing it when we did: the standard advice is to go first thing, because both the queue and the summer haze build through the day. We went in the afternoon and it was still the highlight of the day — but if the forecast is hazy, this is the stop to move to a morning.
Cost: $32 adult (12+), $24 child 3–11, under 3 free — or included in CityPASS C3, which is how we did it. 👉 Our full Skydeck Chicago experience
Grant Park and Buckingham Fountain, after dark
We stayed right across from Grant Park, so this became our evening walk rather than a planned outing — about five minutes from our hotel door.
Go at night. The fountain is lit, it runs its water display on the hour, and the skyline sits behind it. After a flight day it asks nothing of anyone: you walk over, you look, the kids run around, you walk back. It’s free. 👉 Grant Park and Buckingham Fountain
Day 2 — The long one
The biggest day of the three, and the one to look at carefully if your children are younger than ours. It works because most of it is a straight line up and back down Michigan Avenue.
Nutella Café, Michigan Avenue
Breakfast first, and it sets the tone for the day. Waffles, crepes and coffee, and a queue — not a terrible one, but turn up expecting to wait rather than expecting a table. We came by 9am, but we waited at least 30min in the queue 👉 Our Nutella Café review
About 15–20 minutes’ walk south down Michigan Avenue to Millennium Park.
Millennium Park and the Bean
Allow an hour, more if the weather is warm and you use Crown Fountain.
There’s a security check at the entrances — bags opened, a few seconds, no drama, but worth knowing if you’re carrying a picnic.
The Bean itself is twenty minutes: walk around it, walk underneath it, take the photo. What fills the rest of the morning is everything beside it — Crown Fountain, where children are meant to play in the water in warm weather, and Maggie Daley Park two minutes over the BP Bridge, which has the best free playground in downtown Chicago. All of it costs nothing. 👉 Millennium Park with kids
About 25 minutes’ walk north up Michigan Avenue to 360 Chicago, or take a bus up the avenue.
360 Chicago
Our third CityPASS attraction, on the 94th floor of the John Hancock Center. Allow about an hour.
One thing to know before you go up: TILT is not included in CityPASS. It’s an extra $18 per person, and if you’re buying tickets directly you can get it bundled with a drink instead. With four of us that’s $72 to lean out over Michigan Avenue — worth deciding before you’re standing at the counter with two kids who have just seen it. 👉 360 Chicago, the views and the TILT
Giordano’s for deep dish
Lunch, and the one meal in Chicago that’s non-negotiable. Deep dish takes a long time to cook — expect 30–45 minutes from ordering — so order as soon as you sit down, and don’t arrive with children who are already past hungry. 👉 Our Giordano’s deep-dish experience
About 25 minutes’ walk east to Navy Pier.
Navy Pier in the evening
The last stop, on Lake Michigan — restaurants, shops, the Ferris wheel, and the lights coming on over the water. Entry to the pier is free; the rides are paid individually. 👉 Navy Pier with kids
Honest note on Day 2: two observation decks, a full walk up and down Michigan Avenue and a late evening at Navy Pier is a lot for one day. It worked for us with two older boys. With children under eight, move 360 Chicago to Day 3 and let Day 2 finish at Navy Pier before dark.
Day 3 — The free day, and the best one
Our last morning before driving to Milwaukee, and the day I’d protect if the trip got shorter. It’s also the cheapest day of the three by a distance — breakfast, a free zoo, and then we were gone.
Breakfast at Dunkin’
Not glamorous, and that’s the point. On a morning where you’re checking out, doing one more thing and then collecting a car, Dunkin’ is fast, cheap and everywhere, and nobody argues about it. Save the sit-down breakfast for a day you’re not moving hotels.
Lincoln Park Zoo
Free. One of the oldest zoos in the United States and one of the very few anywhere that charges nothing.
Lions, penguins, giraffes — and the Nature Boardwalk, a path around a pond with what is genuinely one of the best skyline views in the city, trees and water in the foreground and the towers behind. Most people photograph Chicago from 300 metres up; this is the one from ground level, and it costs nothing.
Allow 2–3 hours. 👉 Lincoln Park Zoo with the kids
Then the car, and out
From the zoo we went back to collect the rental car and drove north to Milwaukee.
One decision worth copying: we deliberately rented from an office within walking distance of our hotel, so collecting and returning the car meant a short walk rather than a trip across the city with luggage and two kids. Seven days cost us €196.31. We had no car at all for the three Chicago days and never needed one — the car exists for Wisconsin, not for Chicago.
👉 What we did in Milwaukee: the basketball camp week
If you’re not leaving and want one more stop, the Starbucks Reserve Roastery is the easy one — five floors, the largest Starbucks in the world, and free to walk around. It’s also the best rainy-hour rescue downtown. 👉 Starbucks Reserve Roastery, floor by floor
Where we stayed
We were in the South Loop for these three nights, across from Grant Park — which is why the fountain became an evening walk instead of a trip. The location was excellent. The hotel was not, and I wouldn’t book it again with children.
We ended up in three different hotels across the whole trip, including one out near O’Hare that taught me exactly how much a cheap airport rate really costs you in Uber rides and lost mornings. 👉 Where to stay in Chicago with kids: the three hotels we booked and what I’d change
Getting around with kids
We used Ventra cards and walked. No car, no taxis except at the very end of the trip when we’d moved out to the airport hotel. Public transport for all four of us came to €78.77 across the whole trip.
Most of this itinerary is walkable: Willis Tower to Michigan Avenue, Michigan Avenue to Millennium Park, Millennium Park up to 360 Chicago and across to Navy Pier are all 15–25 minutes on foot. The bus and the L cover the rest, and Lincoln Park Zoo is the only stop that really needs them.
Renting a car downtown would have added parking costs and given us nothing.
What these three days cost
Attractions and transport, at what we actually paid in July 2025 for two adults and two children:
| Cost (4 people) | |
|---|---|
| CityPASS C3 — Skydeck, architecture cruise, 360 Chicago | €347.74 |
| Other activities | €41.66 |
| Ventra cards / public transport (whole trip) | €78.77 |
| Lincoln Park Zoo, Millennium Park, the Bean, Grant Park, Buckingham Fountain | €0 |
I’ve kept food out of this section deliberately — our trip ran 13 days including Milwaukee, and splitting the grocery and restaurant spend across it honestly isn’t possible. The full breakdown, flights included, is in the cost post. 👉 What our Chicago and Milwaukee trip really cost
Is CityPASS C3 worth it for this itinerary?
For this exact itinerary, yes — we used it for the three most expensive things we did, and we’d have paid for all three anyway.
It stops being worth it if you’d only really do two of them, or if TILT and the extras pull you past what the pass saves. The maths depends entirely on which three you choose. 👉 Chicago CityPASS C3: the real maths for a family of four
What we’d do differently
- Give the architecture cruise a proper slot on Day 1. It’s the best orientation to Chicago we did and we treated it as a bonus.
- Split the two observation decks across different days — which we did by accident, and it turned out to be the right call. One hazy day doesn’t then cost you both views.
- Decide on TILT before you’re at the counter. $18 a person adds up fast in front of children who have already spotted it.
If it rains
Chicago in bad weather with children is a real problem and most itineraries pretend it isn’t. The indoor options, in the order I’d use them:
- The Field Museum — the big one, easily half a day
- The Art Institute — better with older children than you’d think
- Shedd Aquarium — busiest of the three, book ahead
- Starbucks Reserve Roastery — free, five floors, an hour when you need one
- Both observation decks are indoors, so a wet day is the day to use them — just accept the view will be worse
Everything we did for free
Worth listing, because Chicago is unusually generous:
- Millennium Park and the Bean — including Crown Fountain, where kids can get soaked
- Maggie Daley Park — playground, climbing walls, mini golf
- Grant Park and Buckingham Fountain — best after dark
- Lincoln Park Zoo — a full morning, no ticket
- The Riverwalk and Michigan Avenue
- The Michael Jordan statue at the United Center — free, no ticket needed 👉 how to visit
You could build a genuinely good two-day Chicago trip out of that list alone.
Was three days enough?
For the main sights, yes. We saw what we came for and we weren’t rushing the boys through it. A fourth day would have bought us the Field Museum or Shedd Aquarium without dropping anything — and if you’re building the trip around children rather than around landmarks, that fourth day is the one I’d add.
3 Days in Chicago With Kids: FAQs
Is 3 days enough in Chicago with kids?
Yes. Three days covers the main attractions at a pace children can handle: Skydeck, Millennium Park and the Bean, 360 Chicago, Navy Pier and Lincoln Park Zoo, plus a deep dish pizza and an architecture river cruise. We did exactly this with two boys and did not feel rushed. A fourth day would let you add the Field Museum or Shedd Aquarium without dropping anything.
Do you need a car in Chicago with children?
No. We used public transport and walked, and Ventra cards for our family of four cost €78.77 for the whole trip. Willis Tower, Michigan Avenue, Millennium Park, 360 Chicago and Navy Pier are all within 15 to 25 minutes of each other on foot, and the bus and L cover the rest. A car downtown only adds parking costs.
What should you book in advance for Chicago with kids?
Skydeck requires a timed ticket and the architecture river cruise needs a date and time slot in summer, even with a CityPASS. Book both before you arrive. Millennium Park, the Bean, Crown Fountain, Grant Park and Lincoln Park Zoo are free and need no booking.
Is CityPASS C3 worth it for a family?
It depends which three attractions you pick. We used the C3 pass for Skydeck, the Shoreline architecture cruise and 360 Chicago, and it cost €347.74 for two adults and two children in July 2025. If you would pay for all three separately it saves money. Note that the TILT experience at 360 Chicago is not included and costs an extra $18 per person.
What is free to do in Chicago with kids?
More than in most cities. Millennium Park and Cloud Gate, Crown Fountain, Maggie Daley Park, Grant Park and Buckingham Fountain, the Riverwalk and the Michael Jordan statue at the United Center are all free. Lincoln Park Zoo is one of the only free zoos in the United States and was the best day of our three.
What is the best order to see Chicago in 3 days?
Do the architecture river cruise first, then Skydeck the same afternoon. Seeing the buildings from the water with a guide explaining them, and then looking down on the same buildings from the 103rd floor, makes the rest of the trip make sense. Keep Millennium Park, 360 Chicago and Navy Pier for day two, and use day three for Lincoln Park Zoo. Splitting the two observation decks across different days also means one hazy day does not cost you both views.
How can you eat cheaply in Chicago with kids?
Use the supermarkets. Whole Foods has a hot bar and salad bar where you pay by weight, with seating, and it costs a fraction of a sit-down lunch in the Loop. It is also faster with children, who choose their own food and are not waiting on a kitchen. Across our whole trip we spent 521.52 euros on groceries against 492.05 euros in restaurants, which is what kept a two week United States trip affordable for four people.
What can you do in Chicago with kids when it rains?
The Field Museum, the Art Institute and Shedd Aquarium are the three big indoor options, and the Starbucks Reserve Roastery is a free hour across five floors. Both observation decks are indoors too, so a wet day is a good day to use them, though the view will be poorer.
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