We slept in three different hotels on this trip: one in downtown Chicago, one out by O’Hare, and one an hour and a half north in Wisconsin. Only one of them I’d book again — and it’s the one furthest from the city.
If you’re working out where to stay in Chicago with kids, the area matters far more than the hotel. Chicago’s public transport is good enough that you don’t need a car in the city at all. We didn’t rent one for our Chicago days and never once wished we had. What we did need was to get back to the room at 3pm when the kids were finished, and that single thing decides everything else.
One thing before the numbers: we travelled in July 2025, so every price here is a 2025 price. I’m leaving them in because a real receipt is more useful than a vague range, but check current rates before you budget from them.
Quick verdict
- Stay in the Loop or South Loop if it’s your first time with kids. Millennium Park, Grant Park, the river cruises and Michigan Avenue are all walkable, and you skip the car completely.
- Skip the airport hotels unless you have an early flight. We moved out to one near O’Hare for our last three nights and paid for it in Uber rides and lost mornings.
- You don’t need a car in Chicago. Ventra cards for the four of us covered the whole stay for €78.77.
- If you’re coming for a camp or a tournament, stay out near it. Our week in Brookfield, Wisconsin was the best accommodation of the trip, and the cheapest per night for what we got.
- Book in February for July. Our three hotels came to €1,468.33 for 13 nights for four people in 2025 — but read the note on my travel agent discount, because that isn’t the rate you’ll be quoted.
What we paid, and why you won’t pay the same
Two caveats, both worth stating plainly. First, these are July 2025 prices; rates have moved since. Second, I work in the hotel industry and book with a travel agent discount, so these are what we paid, not what appears on Booking.com. I’d rather show the real receipts with the caveat attached than round everything into a useless “expect €100–150 a night.”
| Hotel | Nights | What we paid, 2025 (4 people) | Per night |
|---|---|---|---|
| Travelodge by Wyndham Downtown Chicago | 3 | €369.60 | €123.20 |
| Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI | 7 | €812.62 | €116.09 |
| Comfort Inn Convention Center — Chicago O’Hare (now Spark by Hilton Des Plaines) | 3 | €286.11 | €95.37 |
| Total accommodation | 13 | €1,468.33 | €112.95 |
We booked the first two in February for a July trip. The third we booked a few days before we needed it, after cancelling a second Travelodge stay — that story is below.
Where to stay in Chicago with kids: the areas, honestly
The Loop and South Loop — first-timers with children
This is where we started, and where I’d start again. You’re walking distance from Millennium Park and the Bean, Grant Park and Buckingham Fountain, the Riverwalk where the architecture cruises leave, and the Art Institute. With kids that walkability is the whole game: you’re never more than fifteen minutes from the room.
South Loop is a little quieter and a little cheaper than the middle of the Loop, and sits on the same train lines. The trade-off — and I learned this the hard way — is that “on the train line” can also mean “under the train line.”
Millennium Park & Chicago’s Iconic Cloud Gate
Grant Park and the Buckingham Fountain
River North and Streeterville — if the budget stretches
Closer to Navy Pier and the Magnificent Mile, newer rooms, higher rates. If you’re travelling with a toddler and want a pool and a proper breakfast in the building, this is where you’ll find them. We didn’t stay here, so I won’t pretend to review it.
Near O’Hare (Des Plaines / Rosemont) — only for the last night
Cheaper per night, and the trade-off is real: you’re a 40-minute-plus journey from downtown, and with kids that journey happens twice a day. Worth it if you have a 6am flight. Not worth it if you still have sightseeing left, which was exactly our mistake.
Brookfield and the Milwaukee suburbs — if you have a reason to be there
We had one: the boys were at a basketball camp near Milwaukee, and the week we spent out there turned out to be the most comfortable part of the trip. If you don’t have that kind of anchor, staying this far out means renting a car and adding ninety minutes each way to Chicago.
Milwaukee Bucks summer camp experience
Hotel 1: Travelodge by Wyndham Downtown Chicago — great location, and that’s the list
65 E Harrison St, South Loop. Three nights, €369.60 for two adults and two kids.
I booked this one on location alone and the location genuinely delivers — ten minutes’ walk to Grant Park, minutes to the Red Line, the whole downtown core on foot from the door. If the room had been quiet, this would be an easy recommendation for families who’d rather spend their money on the city than the hotel.
We were on the seventh floor, in a room whose windows faced the metro station on one side and the road on the other. That’s the entire review in one sentence. We heard the trains until late at night, and once the trains stopped we heard sirens — police and emergency vehicles, all night, at road level with nothing in between. On a trip where you’re walking eight hours a day, that isn’t a minor irritation; it’s the difference between kids who can do the next day and kids who can’t.
So I asked to be moved. Reception wouldn’t move us. Not “we’re fully booked and I’m sorry” — just no.
That refusal is what decided it. A dated room I can live with. A small bathroom I can live with. A front desk that won’t attempt to solve a problem for a family with two exhausted children is a different thing, and it’s why I cancelled the three nights I’d booked here for the end of the trip and paid to sleep somewhere else.
If you book it anyway: ask for a room on the courtyard side, away from the tracks and the road, and get that confirmed in writing before you arrive. The noise is a function of which window you get, not of the whole building.
Would I book it again? For a couple who are out all day and just need a bed in the centre of everything — possibly. With children who need to sleep — no.
Hotel 2: Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI — the one I’d book again
Brookfield, west of Milwaukee. Seven nights, €812.62 for four.
This was our base for the week the boys were at basketball camp, and it’s the hotel of the three I’d rebook without hesitating.
The room was on the first floor with two queen beds — the simplest possible setup for two adults and two kids, and the one that actually works, because nobody is sleeping on a fold-out. Breakfast was included and, unlike a lot of included breakfasts, it was properly generous. We looked forward to it, which after a week of early camp mornings says enough.
The part the kids cared about: two indoor pools, a big one and a small one. They came back from training and went straight in, every single day. If you’ve ever tried to burn off a ten-year-old’s remaining energy after a full day of basketball, you’ll understand why that mattered more than anything else in the building.
The camp was about a ten-minute drive away. The area is quiet in the way American suburbs are quiet — nothing happening, which is exactly what you want when the schedule is early starts and physical days. We rented a car for these seven nights, €196.31, picked up from an agency near the Travelodge so we could collect and drop off on foot from where we were already staying. Fuel came to €50.63 for the week, and we paid for parking twice — €5.89 and €5.82.
Would I book it again? Yes, and we would happily go back for another camp year. If you’re coming to the Milwaukee area for a camp, a tournament or a game, this is the model: stay near the venue in something with a pool and a real breakfast, and treat Chicago as a separate leg.
Hotel 3: Spark by Hilton Des Plaines (formerly Comfort Inn Convention Center — Chicago O’Hare) — quiet, and too far
2175 E Touhy Ave, Des Plaines. Three nights, €286.11 for four, booked a few days ahead after we cancelled the second Travelodge stay.
A note on the name: we stayed here when it was the Comfort Inn Convention Center — Chicago O’Hare Airport. It has since become Spark by Hilton Des Plaines Chicago O’Hare, at the same address, so search for both.
After the Travelodge, the silence here was the entire point, and we got it. Genuinely calm — nobody slamming doors, no sirens, no trains. We were on the second floor. The hotel was mid-refurbishment during our stay and not every room was available, which is worth knowing because it cuts both ways: our room was very nice and very clean, with what felt like brand new bedding, while the bathroom was too small and not especially pleasant. Given the refurbishment and the rebrand since, the bathroom is exactly the kind of thing that may well have been fixed. I’d check recent photos rather than take my word for it.
Breakfast was included, but light. If your children eat properly before a day of walking, plan to top it up.
The problem wasn’t the hotel. It was the geography. It’s too far from the city, and by this point we had already returned the rental car, so the daily routine became: Uber to the metro station, train into the centre, train back, Uber home. Our whole trip’s Uber and Lyft spend was €16.94 and every euro of it went on this stretch — trivial in money, expensive in the forty minutes at each end with tired kids.
Would I book it again? For a night before an early flight out of O’Hare, yes. As a base for sightseeing, no — and definitely not without a car.
What I’d book differently next time
- All the Chicago nights in one place. Three hotels in thirteen days with two kids means three check-ins, three re-packings, and two days half-lost to moving.
- South Loop or Loop, but not the cheapest room in it. The €20–30 a night I saved at the Travelodge cost us sleep, and I spent it again on the replacement hotel anyway.
- Ask which way the windows face. Not the star rating, not the average review score — the window. That’s the one question that would have changed this trip.
- Check the cancellation terms before booking the cheap rate. Being able to cancel those last three nights penalty-free is the only reason this story ends well.
How to choose by the age of your kids
Toddlers and under 5 — prioritise a pool, a real breakfast and some separation in the room. River North or Streeterville, and accept the higher rate.
School age, 6–11 — the Loop or South Loop. At this age walkability beats facilities: getting back to the room mid-afternoon is worth more than a pool they’ll use once.
Teenagers — anywhere on a train line. What matters is being close enough that you’re not negotiating about transport every morning. And if they play a sport, the Brookfield lesson applies: a pool after training is not a luxury, it’s how the evening stays calm.
Practical things worth knowing before you book
- You don’t need a car in Chicago. We had none for our city days and never needed one. Downtown hotel parking is an expense you can avoid entirely.
- Get Ventra cards. Public transport for all four of us was €78.77 for the trip.
- Book hotels around five months out. We booked in February for July.
- If you’re doing Skydeck, 360 Chicago and the architecture cruise, price the CityPASS first — ours covered all three for the four of us at €347.74 in 2025. 360 Chicago / CityPASS C3
Frequently Asked Questions: Where to Stay in Chicago With Kids
What is the best area to stay in Chicago with kids?
The Loop and South Loop are the best areas to stay in Chicago with kids, because you can walk to Millennium Park, Grant Park, the Riverwalk and Michigan Avenue without using transport. We stayed in the South Loop and never needed a car for our days in the city. River North and Streeterville are the alternative if you want newer rooms and a pool, and they cost more.
Do you need a car in Chicago with children?
No. We had no car for our days in Chicago and never needed one. Public transport for our family of four cost €78.77 for the whole trip using Ventra cards, and the downtown attractions are close enough together to walk between. A car only becomes necessary if you are staying outside the city or driving up to Milwaukee.
Is it worth staying near O’Hare airport with kids?
Only if you have an early flight. We spent our last three nights near O’Hare in Des Plaines and the hotel was very quiet, but it is too far from the city for sightseeing. Without a car, every day meant an Uber to the metro station and a train into the centre, which added around 40 minutes at each end with tired children.
How much do hotels in Chicago cost for a family of four?
We paid €1,468.33 for 13 nights across three hotels for two adults and two children in July 2025, an average of €112.95 per night. Those rates include a travel agent discount and are 2025 prices, so current public rates will be higher. We booked five months in advance for a July stay.
Where should you stay for a basketball camp near Milwaukee?
Stay near the camp rather than in Chicago. We spent seven nights at the Country Inn & Suites in Brookfield, about a ten minute drive from the camp, in a room with two queen beds, included breakfast and two indoor pools the children used every day after training. It was the most comfortable stay of our trip and we would book it again.
Is the Travelodge Downtown Chicago good for families?
The location is excellent and the price is low, but we would not book it again with children. Our seventh floor room faced the metro station and the road, so we heard trains late into the night and sirens after that, and reception refused to move us. If you do book it, ask for a room away from the tracks and get it confirmed before arrival.
