Chicago With Kids – A Two Day Itinerary

Things To Do With Kids In Chicago, Ilinois – A 2 Days Itinerary

City trips with kids are exhausting. Who did I think I was kidding booking 2 days in Chicago with kids at the end of our visit to see friends in the States!? All they were really interested in was scouring Target for American candy and bagging a deal in the Levi’s outlet mall – how were we ever going to convince them that they needed to forget consumerism for just one minute and enjoy the architecture and urban-cool?

FOOD, that’s how.

A few months ago, when I started researching a few fun things to do in Chicago with kids, I quickly discovered how much of a foodie city it is. Chicago food even has its own hashtag on Instagram! And, it was becoming quite clear we were going to have no need for our belts by the end of 2 days. Chicago dogs, deep-dish pizza, and don’t even get me started on all the donut stops we made!

But, there are so many things to do with kids in Chicago aside from trying all its awesome food choices! Zoo’s, monuments, parks, shopping and much much more. Chicago turned out to be a highlight for our family trip to the States, and we think you will love it too.

Our itinerary for what to do in Chicago with kids is not an exhaustive list – we were only there for a short while. But, we think we did a great job of incorporating the city’s highlights with the best things to do with kids. Chicago could entertain young ones for a long time! So here are our highlights, all the places worth seeing and of course, some hidden gems too! All tied together with the places you need to stop for all the best eats in Chicago. 

cityscape view of Chicago from Lincoln Park Zoo

Family Friendly Hotels In Chicago


First off, you need a good family friendly hotel in Chicago, in a good location, and somewhere that’s not going to cost an arm and a leg. After a lot of research we found an awesome Chicago hotel in a brilliant location and I’m not going to lie – I did a little happy dance, possibly even a cartwheel, when we opened the door to our room! Best Western, River North is centrally located downtown, only a 5 to 10 minute walk from all the main sights and is really close to some great places to eat with kids too.

The room is so large (and stylish), roomy enough for 2 double beds and a sofa bed, comfortably sleeping our growing 3 kids. There is on-site parking if you need it, for a little extra charge, and the staff couldn’t have been more helpful.

The hotel itself has a heated indoor swimming pool on the top floor and it was nice to see they weren’t even remotely uptight about children swimming without adults, plus you don’t need those ridiculous bathing caps that other hotels insist on.

Next to the pool is an outdoor decked area with amazing views over the city and you’re more than welcome to take your cocktail up there to lounge on a bed and soak up the cityscape, whilst the kids are dive-bombing in the pool. Travelling to Chicago with kids can be exhausting so having this rooftop area to relax in was definitely the best selling point for us.

The view from our bedroom window
The best hotel for families in Chicago, without a shadow of a doubt – room view

Things To Do In Chicago With Kids

Day 1 In Chicago With Kids


Before you spend two days in Chicago you might want to get your bearings. It’s a large city and looks so cool from above, which is probably why the world and its dog head to the Willis Tower for the SkyDeck vantage point. It’s one of those cool things to do in Chicago if you have the money and, I’m sure the views are breathtaking but when you’re travelling en-masse with kids in tow you have to weigh up your priorities and decide if you think $25 per person is within your budget or if you’d rather blow $100 as a family on something else. We opted for something else…

So, after a traditional Chicago breakfast of coffee and vanilla glazed doughnut topped with streaky bacon at Do Rite Donuts on West Randolph Street we started our day at the Richard J Daley Centre over the street. A Chicago hidden gem with an equally amazing view!

This is the official Civic Centre (or courthouse) of Chicago and once upon a time was the tallest building in Chicago. The lobby is quiet and you start to think you shouldn’t be here, but after a quick word with a security guard as to whether we could see the view he was absolutely delighted we were there in his building, and not at the Willis Tower.

You have to go through a metal detector so be sure to leave your AK47 at home that day, and you will need to take out your camera battery to proceed any further. Don’t worry though – phones are allowed.

Take the lift to the 30th floor, which includes an obligatory stomach lurch at the speed the lift gets so high – another highlight for the kids! Once you’re at the top you’re actually mingling with a handful of lawyers and defendants who seem bemused to be sharing their workday with a young family of 5 but Chicagoans are so friendly and are more than happy to show off their city.

The view is only 180 degrees really but boy are you high and it’s so beautiful –  it’s also quite nice to think you just saved yourself a hundred bucks.

The best free view in Chicago that's not the Sky deck
Picasso monument - a must see Chicago for kids

The Richard Daley building is backed by a lovely courtyard too which just so happens to be home to a huge Picasso sculpture that no one else seems to be noticing. There are nearby in-ground fountains to appease the kids as you admire the real masterpiece here. The untitled 50 foot landmark was gifted by Pablo to the city in 1967 and has shown up in a few movies over the years like The Fugitive, Batman – The Dark Knight and The Blues Brothers.

Tip – Our next stop is The Bean but if you have the time and would like to see some classic Chicago sights, now might be the point to take a little detour. Macy’s (N. State street) and the Chicago Theatre (Lake Street) are a stones throw from the Richard Daley centre, but in the opposite direction to The Bean. Macy’s is a beautiful department store and those in the know will check out their famous Tiffany ceiling made of gold and mosaics. But there are lots of other lovely features worth seeing, like the chandeliers and the Walnut Room Restaurant. And, can you really say you have been to Chicago if you haven’t taken a picture of the Chicago Theatre sign??


What everyone comes to Chicago to do – see the huge silver kidney bean. It really is something else, and having our very own Anish Kapoor sculpture in my hometown of Nottingham, I feel an even stronger connection to this blazing beauty.

Unless you can be bothered to rise at 5am (which let’s face it – has a stronger probability if you are travelling with kids) then you will have to share Cloud Gate with 50 million gazillion other people. But it is epic! And, the little reflections of people in the highly polished steel curves kind of only add to the beautiful effect anyway. 168 steel plates are seamlessly welded together to form an object which resembles something of extraterrestrial origins – it’s like a UFO birthed a silver womb and one day E.T. will emerge with vague humanlike qualities after watching Chicago humans from the other side of the mirror for decades.

The Bean - best things to do Chicago, Illinois
Things to do in Chicago kids!
Cloud gate, Millenium park, Chicago - must do!
The bean, or cloudgate, is one of the top things to do in Chicago with kids

Cloud Gate is situated in Millenium Park which is just a portion of the green space known as the front lawn of Chicago. Combined with Grant Park this is one of the best places to take kids in Chicago to unwind and get away from the hustle and bustle. The endless skyscrapers can get a bit claustrophobic after a while.

Grant Park – a fun place to take the kids in Chicago

Within the 319 acres are fountains, play parks, climbing walls, a ‘skate and scooters ribbon’, mini-golf, shaded picnic areas and the interactive video sculpture at Crown Fountain. This is where I would spend my $100 – there are SO many fun things to do in Chicago with kids but half an hour on the climbing wall, then a game of crazy golf – that’s great value for money as far as the younger family members are concerned!

Tip – Download the Millenium Park app for up-to-date information on events and entertainment going on in the park.


Giordano’s is a Chicago-based chain restaurant serving traditional deep-dish pizza since 1974 and does a great kids menu for under $5, including a drink. You have to have deep-dish pizza in the city of deep-dish pizza at least once!


One of the top family attractions in Chicago, Navy Pier makes it to all of the guidebooks…but I just don’t get it! Maybe we hit it at a bad time (there certainly seemed to be a lot of construction going on)? But, as far as I could tell, it’s just a pier with a big wheel, a carousel and a few overpriced restaurants – it probably saw more entertainment the summer of 1918 when it was used as a jail for ‘draft dodgers’. But I guess you still have to put it on your Chicago trip itinerary – it is one of Chicago’s main attractions for families.

Ok, Ok, it has fireworks too. And, actually, it looks fantastic all lit up at night, plus there’s a bit of a buzz in the evening. BUT… the fireworks are only displayed in Summer on a Wednesday and Saturday so, you know, if it’s your weekly chess night or bowls club, well then – you’re screwed! Live music too by some pretty decent bands, but again – only in the Summer.

Tip – If you’re visiting Chicago in the winter months (and by winter, they mean October to May), Navy Pier does have a few indoor attractions to get you out of the cold Chicago wind : The funhouse maze at Amazing Chicago gets a good report as does the Chicago Children’s Museum.

Day 2 In Chicago With Kids


You’re in Chicago – you have to ride the ‘L’ at some point! L, standing for Elevated, is the quick train system that gets Chicagoans from A to B. It’s a massive part of Chicago’s history and heritage.

Chicago has always dreamt big and even after the Great Chicago Fire in 1871, which obliterated 3 square miles of mainly wooden buildings, the city immediately got to rebuilding. But, skyscrapers rose so quickly that before they knew it, the streets below them were congested and stank of horse poo! (I made that last bit up, but it’s probably true) Real estate soared in price so the only reasonable answer was to build the tracks above the existing roads. Plus, they’d need it for when the day came to film ‘While You Were Sleeping‘. (Incidentally, if you like scouting out film locations as much as me, it’s the Randolph/Wabash station you need.)

From above, the ‘L’ looks a bit like a Catherine Wheel firework photographed slowly – a downtown loop that shoots off branches in all directions, to every corner of Chicago.

For a bit of Chicago family fun, my advice would be to catch the Purple or Brown line at Merchandise Mart and head in the direction of The Loop. Complete a full circle of The Loop to take in as much of downtown as possible just for the Chicago views. Then retrace your steps up the line till you can get off at Sedgwick then walk a couple of minutes to the southwest corner of the Lincoln Park Zoo.


Literally the wildest place you’ll visit in Chicago! Open 365 days a year and completely free, the zoo is an absolute must and one of the best things to do in Chicago with kids, no matter their age.

Our visit was definitely one of the highlights of our stay and the beauty of it being free is that you don’t feel like you have to string it out to get your money’s worth – if you only have a penchant for polar bears and penguins then you only need to visit the polar bears and penguins.

I challenge you not to linger though, and especially when you hear about the wonderful work the zoo are doing in partnership with the conservation and science programs that are ongoing. Scientists are using the zoo to study the animals and are working hard to combat threats to wildlife populations and develop strategies in animal management, so there’s no need to feel bad about the $20 you spent in the gift shop – it’s money funding a good cause. You even get to see some of the scientists at work.

For us the best bit was watching the apes so close up, only a pane of glass between you and these beautiful primates – I think we spent half an hour in the monkey house, fully mesmerized.

It’s not just a zoo either, close to the south end of the park is a spot many choose to have their wedding photo’s taken at because, well take a look below at our photo’s and you’ll see what an epic city-scape you can fit in the frame.

And, once you’ve had your fill of wildlife you just so happen to be in a really upscale neighbourhood with some excellent choices for lunch or even just a quick snack. Lincoln Park area backs on to a neighbourhood called Sheffield which is also a great place to find unique gift shops and beautiful coffee shops.


Take a walk up North Clark Street for a Firecakes donut, or an empanada at Lito’s. Or if you’re feeling brave, you may want to risk a few notoriously thrown insults when you order your Chicago dog at Wiener Circle. Failing that, the milkshakes at Five Guys are good for a takeaway too. This is definitely the area to find a few unique eateries with some infamous Chicago delicacies. You’re not a million miles away from Oz Park either, if you fancied collecting some food to go and want to enjoy it beneath some Wizard of Oz sculptures, just to bring a bit of randomness to your day.

Hop back on the ‘L’ over at Fullerton and take the brown or purple line again, back into the metropolis for your last evening in the windy city. Refuel with a sandwich from Al’s Beef; their wall of fame is a testament to how good they are – overstuffed Italian beef sandwiches are made from slow-cooked joints of beef then dipped in gravy and stacked into a sourdough bun. Honestly, the best food we tried in Chicago! (Ontario Street or Wabash Avenue)


You’ve seen the loop in the day, you’ve ridden it from your elevated throne, now all there is left is to see downtown at night and there is no better place to see it than from the Riverwalk

Six blocks of uninterrupted landscaped paths run alongside the Chicago River and it’s a fantastic position to view this magnificent twinkling skyline. offer contribution-based tours explaining all about the architecture that surrounds you and they even hold tours at night. Alternatively, just take a stroll and enjoy the view.

If you would like to impress the kids with some cool facts about the skyscrapers you see along the River Walk then click through to my other post – Chicago Architecture Unwrapped For First Timers.

interesting facts about Chicago's buildings for kids

More Things To Do In Chicago With Kids…

Being the Windy City and suffering from a tediously long winter some years, here are a few other suggestions of fun things to do in Chicago for kids if they need a bit of entertainment, or even if rain has stopped play…

  • See a baseball game at the world famous Wrigley Field
  • Visit the Field Museum to meet Sue the T-rex and find out how mummies are made
  • Watch the Dolphins and Penguins at Chicago’s Shedd Aquarium
  • Find out what it’s like to travel to outer space at the Adler Planetarium
  • If you’re in Chicago with teenagers, you will definitely want to let them do a bit of shopping on Magnificent Mile.
  • If you have a car and a bit of spare time before your flight, check out the precious stones and gems at the little free  museum called the Lizzadro – well worth 30 minutes of your time and perfect if you’re looking for things to do around Chicago airport.

So, there you have it – our two days in Chicago itinerary for families. No one will leave disappointed! (or hungry for that matter) Have you been? Can you recommend any more places that are good for families in the Chicago area or any more excellent food ideas? Do drop me a line below, I’d love to hear…

pin for later…

There are loads of things to do in Chicago with kids and we have the perfect 2 day itinerary to make sure you see all the highlights and you have the best time with the family! #chicago
A 2 day itinerary for Chicago with kids - all the best attracions, museums, parks and places to eat for families. #chicago #ilinois #usa #kids #thingstodo

24 Comments Add yours

  1. Adrianna says:

    I’m so glad I discovered your blog on Pinterest! Your photos are breathtaking… you are quite a talented photographer! And your tips for visiting Chicago were so helpful. The reader experience on your blog is so enjoyable: no annoying ads popping up to cause distraction. Thank you for that!!

  2. jane Taylor says:

    Wow! Loads of fabulous information to digest! MMr T would love those beef sandwiches! Mmmmm! Love your brilliant tip for getting a free view across Chicago, too.

  3. Alex, I love your travel stories and recommendations and this is a part of the States we haven’t visited yet so it is bookmarked. Thank you for linking again. #TweensTeensBeyond

  4. Another wonderful post! You don’t let the grass grow under your feet do you?! I am in awe of your energy and ability to seek out all of these finds Alex. I had a brief visit there when Lily was little. I have a friend in Chicago and when all the stars are aligned, I hope to go back and repeat. We did, as you know, see the Bean! Other than that, you have left me standing. Quite literally in the case of these high level daredevil stunts you are undertaking of late. Thanks for sharing with #tweensteensbeyond

    1. Alex says:

      I know – I show go into adventure-travel-writing! It’s these teens I’m trying to keep up with. Brilliant you have a ready made tour guide next time you return to Chicago!

  5. Sharon Parry says:

    This is a super useful post! We did New York last year with our three and I love the idea of another US city soon. This looks perfect! Everything I needed to know. Thanks so much for sharing with us at #TweensTeensBeyond

    1. Alex says:

      I mean it’s not New York but it is an awesome city! And the food….

  6. This is perfect, thank you – we will be there for four days this coming summer and I know my kids will be tired of sightseeing by then so it’s great to read how you all got on. I’ve made some notes! #tweensteensbeyond

    1. Alex says:

      I have another post about the architecture too – some cool facts about the architecture. Have w fab time there!

  7. scots2travel says:

    An army marches on its stomach, so does a family of four. You’ve outlined a v cool trip here. Would love to visit now.

    1. Alex says:

      It’s a fab place for families.

  8. Katy says:

    Visiting from #tweensteensbeyond. Our family loves Chicago and as we are in Michigan it’s the nearest big city within driving or train distance. On our last visit we took in the Museum of Science and Industry. We took an Uber as it’s not downtown but it was amazing–especially the submarine!

  9. Looking forward to taking my kids to Chicago some day, it’s such a great city. Millenium Park is awesome. Pinning for when we eventually make it! #citytripping

  10. Great itinerary! We spent some one in chicago a few years ago – the last time my husband got ill. We did a lot of the museums as we went there in winter. Brrrr. So impressed with your research and discovering another high vantage point. I preferred the Hancock tower to the Willis. Was a bit more modern (so you didn’t miss out) For those children into their art, the Art Institute of Chicago is good. I absolutely love the top Bean picture. What lens did you use. V impressed. Thanks for linking #citytripping

    1. Alex says:

      That’s not a lens – that’s just the reflections you get inside the bean, it’s amazing.

  11. Hi there, I’ve never been to Chicago and I honestly didn’t know much about it…except for ‘While you were sleeping’ lol. I loved all of your recommendations and Chicago is now on my list of cities that I would like to take my kids to one day. We totally need to try some of that deep dish pizza!!

    1. Alex says:

      You totally do 😉

  12. Nicola says:

    We loved the Cloud Gate. We there early morning due to jetlag and had whole thing to ourselves!

    1. Alex says:

      That’s a good idea actually – use the jet lag to your benefit!

  13. Shobha says:

    I haven’t been to Chicago since I was in law school there. I agree Navy Pier is overrated. I’d love to take my kids – they would be all over the Chicago deep dish pizza!

    1. Alex says:

      I’m so glad it’s not just me re. Navy Pier.

  14. Not sure about the bacon topped do-nut but a top tip about not doing the Willis Tower and that is one giant lens ball! #CityTripping

  15. Oh this is perfect! We’re considering a weekend trip to Chicago this summer! That Macy’s ceiling is amazing and I too love a good Insta-win! Pinned for later!! #CityTripping

    1. Alex says:

      Macy’s has quite a few insta-worthy spots in it, not just the ceiling, so you must go! 😉

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