Visiting Chicago with kids – One of the best US cities to visit

We recently took a trip to Chicago much to the surprise of friends and family who asked what’s there to do in Chicago.

Whilst it might not be an obvious choice of places to visit in the US with kids (with many UK families overlooking the Windy City for the likes of New York, Orlando, Boston and Los Angeles) they are missing out – Chicago is one of the most underrated cities in the USA.

Since our visit, Chicago has easily become one of our favourite cities in the world. There is so much to see and do for families, you could spend a fortnight here and still not see everything.

Here’s a look at what we got up to during our five days in Chicago.

Day 1

We stayed the night before our flight at the impressive Hilton Heathrow T5 (you can read our review here). I would really recommend this hotel especially if you are flying from Terminal 5 with British Airways but for Terminal 3 it was a little more complicated to get to, especially when our Sat-Nav got us lost and added another 15 minutes to the standard 20 minute transfer time.

Getting there

We flew out of London Heathrow Terminal 3 with American Airlines for our 9 hour flight to Chicago.

This was our first time flying as a family with American Airlines and apart from the check-in process at Heathrow which was a little chaotic, the flight on their new Dreamliner planes was really good with on-board wifi, friendly crew (they gave the girls American Airlines crew pin badges) and a huge range of entertainment options to keep all of us entertained.

If you are flying American Airlines, I would strongly recommend that if you don’t have enough air miles to stretch to fly business, then you book into their Premium Cabin, which offers more space and better amenities compared to economy which at nine seats across on the Dreamliner is a little cramped.

We arrived into a snow covered Chicago O’Hare airport much to the delight of Chloe and Holly after a storm had dumped a record-setting snow amount for Chicago for Halloween.

While you can get a train or taxi into the city, we skipped the hassle and had a pre-booked SUV (approx. $115 through our hotel) which was waiting for us. A 50 minute ride later, we checked into the Swissotel Chicago, which was our accommodation for 5 nights.

Checking into the Swissotel Chicago

We spent a lot of time researching where to stay in Chicago and we were really happy with our choice at the Swissotel Chicago.  If you are planning a stay at the Swissotel, I highly recommend booking one of the kids suites if available.

We walked into our room on the 35th floor, which could be best described as our own private apartment with two bedrooms, 3 bathrooms and a huge living area. Best of all, from the kids perspective, was that their double room had age appropriate toys, books, games and a really cool tepee and skittles set up in the living area.

Because of the unique triangular design of the hotel our rooms also had some of the best views of the city of Chicago from its numerous vantage points. One of my favourite things to do each morning was opening the curtains to see the sunrise over Lake Michigan and the magnificent skyline of the city.

After enjoying the treats left for us in our kids’ suite at the Swissotel Chicago, we headed for the Magnificent Mile.

Magnificent Mile

The mag mile is the main shopping street in Chicago and home to some of the best shopping in the world – much to our delight!

This street is also home to buildings such as the Chicago Water Tower which survived the Great Chicago Fire of 1871.

As it was Halloween, combined with the snow on the ground, the streets and shops of the Mag Mile were deserted, so we basically had a VIP experience at each store we visited. The Magnificent Mile is a shoppers dream and we loved it, with over 460 stores to choose from along with lots of luxury hotels and great restaurants.

Before our trip, Chloe and Holly had found out that the biggest American Girl store in the world was in Chicago, and they couldn’t wait to re-visit after having so much fun at the New York store last year.

En-route we stopped off at the Disney store and for some Halloween candy at Dylan’s Candy Store. This is no ordinary candy store, launched by Ralph Lauren’s daughter. It’s like visiting a store that Willy Wonka himself would be proud of, with a huge range of sweets and chocolates to choose from.

American Girl Place

When we finally got to American Girl Place the look of excitement on the girls’ faces was priceless.

For kids who love dolls, there is no better place than this and it’s huge. Spread over two floors it’s the size of a department store in the UK with everything your doll would ever need.

Our plan was to have a quick look at the store so we knew where to go for the morning yoga and breakfast experience in two days’ time that we had pre booked at American Girl before we left, but we had to coax the girls out over an hour later with their first of many AG shopping hauls here so we could get dinner.

La Pizza & La Pasta at Eataly

With the jet lag starting to take effect we had dinner at Eataly before we called it a night. This isn’t your typical Italian restaurant – it’s an Italian dining concept and we love it here after visiting the New York restaurant.

At La Pizza & La Pasta at Eataly there was a wide selection of freshly made and delicious varieties of pizza and pasta – the food here is amazing.

Get a CityPASS

Tip – I would recommend taking a look at the Chicago CityPASS especially if you are planning on visiting several of the city’s top attractions. It not only saved us money it also provided us with ideas of where to take the kids that we might have overlooked. 

Day 2

The next morning because of the time difference (-6 from the UK) we were up bright and early. We had breakfast at the hotel before making our way to the 100-storey John Hancock Center, one of the tallest and most distinctive skyscrapers in the city.

360 Chicago

The 360 Chicago Observation deck on the 94th floor offered breathtaking 360 views of the skyline of Chicago and Lake Michigan but our highlight was ‘Tilt’ Chicago’s tallest thrill ride which literally tilted us out 1000ft above Michigan Avenue as we hung onto the bars of the panes of glass.

Okay, Tilt at the John Hancock centre is not for the faint hearted, but it’s easily one of the most unique and fun things you will do at the top of one of the world’s tallest buildings.

Tuk Tuk Chicago Tours

To get to our next attraction, we travelled in what has to be one of the coolest and eco-friendly ways to explore the city. Who needs taxis or Uber when you have a Tuk Tuk – one of Chicago’s newest forms of transportation.

We pre-booked an hour tour with Tuk Tuk Chicago before we arrived in the city and right on time our 3 wheeled electric vehicle arrived along with our personal tour guide and TukTuk captain Shaun, who was really friendly and knowledgeable, pointing out landmarks and points of interest to us, as we zipped through the streets.

On a freezing cold day it was a really fun and warm way to get around the city. It’s the little touches that stood out like the heated seats and blankets plus the puzzled looks of pedestrians and cars as we whizzed past at 25mph.

Cloud Gate – the Bean

Our Tuk Tuk stopped off so that we could wander around Millennium Park and visit one of Chicago’s most popular attractions, Anish Kapoor’s Cloud Gate or as it is better known as “The Bean”, a 12ft high iconic piece of modern art made from 168 highly polished stainless steel plates.

The girls loved walking under it, touching its shiny mirrored surface and seeing their image reflected. We had lots of fun here taking photos especially with the city’s famous skyline as a background – it’s the perfect selfie spot.

Our Tuk Tuk was waiting to take us to our final destination – the Shedd Aquarium, which is not to be missed when visiting Chicago.

We used our CityPASS to gain entry which was super easy and something I would highly recommend if you want to save money. We use these wherever they are available at cities across America. (you can find out more about our Chicago CityPASS experience here).

Shedd Aquarium

It’s one of the largest indoor aquariums in the world, with over 30,000 different species of marine life from all over the globe and was one of our favourite things to do in Chicago.

The Caribbean Reef offered views of marine life including stingrays, sharks, colourful fish and sea turtles but our highlight was at the Abbott Oceanarium, home to dolphins and Beluga whales.

The 4D theatre is also worth stopping by as we learnt about Sea Monsters (although we got a little wet with the 4D special effects much to the delight of the kids).

Adler Planetarium

A short walk along the coastline from the aquarium was the Adler Planetarium, the first of its kind in the Western Hemisphere. Along this walkway you can get some of the best views of the city skyline.

Our CityPASS booklets provided us entry and its exterior is just as impressive as the amazing space exhibits inside with lots of interactive displays and activities to learn about the universe and space travel.

Make sure you don’t miss the Sky Theatre show, which is projected on the 68ft dome of the historic Zeiss planetarium, where we took an interactive space mission around our solar system.

Robert’s Pizza and Dough company

After some down time to recharge our batteries at the Swissotel, we took an Uber to Robert’s Pizza and Dough company for dinner.

We’d heard great things about the pizzas here at this trendy new restaurant favoured by locals (always a good sign) plus the setting was perfect, next to the Chicago River in Streeterville.

It’s famous for its artisan pizza and I can see why it’s so popular. The food here is delicious coupled with great friendly service so it’s well worth visiting. The Garvey family, who run the restaurant, have a secret recipe dubbed ‘Za Dough’ providing a pizza crust which was really unique.

We ordered three pizzas – cheese and tomato for the kids, pepperoni for Ian and caramelised onion for myself, all of which were amazing – we were a little ambitious though, the pizzas here are huge!

Disney’s Nightmare Before Christmas at the Auditorium Theatre

We wanted to experience Halloween in the USA and to end the day we had tickets for Disney’s Nightmare Before Christmas at the historic and beautiful Auditorium Theatre.

The girls arrived in their costumes to enjoy the pre-show trick or treat event where they filled their bags with American candy in readiness for the performance.

Watching this classic movie with the orchestra of the Chicago Philharmonic performing the music live, which was such a unique Halloween experience that we won’t ever forget. We loved it.

Day 3

Morning Yoga at American Girl Place

We began our third day with a morning yoga session with a difference. We booked the girls onto learning yoga with their dolls at their favourite store American Girl, which provided lots of laughs and giggles as they came up with some of their own poses.

After the class, breakfast snacks and drinks were provided. If you are visiting Chicago and your kids are American Girl fans they will love this unique and fun way to start their morning, but make sure you pre-book as these events can sell out quickly.

It’s these little moments when you look at how much fun they are having which is why travelling is so worthwhile. These are memories that they will hopefully remember forever.

Riverwalk Chicago

We did a little more shopping on the Magnificent Mile and just enjoyed walking the streets of the city taking in the sights.  Chicago is also home to the worlds largest Starbucks (which was opening a few days after we left the city.)

Chloe and Holly loved being at the Friends set, which was on the Mag Mile and we had to stop in Ghiradellis chocolate store (why don’t they have these in the UK?)  However in Chicago you also have to try the chocolates at their most famous chocolate store Fannie May, their creations are delicious!

Two of my favourite buildings were on the mile including the beautiful Wrigley Building and the Tribune Tower, the architecture in Chicago is breathtaking.

We headed down to the Chicago Riverwalk home to restaurants, cafes and bars ready to catch our cruise. We much preferred the Chicago Riverwalk to the one at San Antonio Texas.

First Lady Sightseeing Cruise

The First Lady Architectural cruise was another highlight of our stay in the city, so thanks for this recommendation.

This cruise was a really good way to see the city from a different perspective. Ian and I spent the majority of our time on deck and it was very hard not to keep looking up at the neck-straining skyscrapers – they are so impressive, the newest of which is the Trump Tower, dominating the city skyline.

The girls meanwhile were happy in the warmth of the inside cabin as they enjoyed hot chocolate whilst taking in the views.

We did manage to coax them out onto the chilly open air deck of the boat so we could get some family photos along with Instagram worthy snaps of the skyline.

Our knowledgeable guide offered us insights into the city’s past and future as well as the history and architecture of the buildings, as we explored a wide area of the city on our 90 minute journey.

Apple Store

The Apple store on the banks of the Chicago River was mentioned on the cruise and is one of the most expensive stores Apple has built, costing a cool $60 million so after the cruise, we went to check it out.

It was the most impressive Apple store that we have been to, being next to the river is amazing and inside we watched some of the photography masterclass by pro photographer Nigel Barker, who I remember from the TV show America’s Next Top Model.

Navy Pier

We took an Uber over to Navy Pier, a 3,300ft pier stretching out onto Lake Michigan and home to the cities iconic ferris wheel and the children’s museum.

As the majority of the fairground attractions at the pier were closed because of the winter season (apart from the wheel) we called into the Crystal Gardens, a beautiful indoor garden with fountains at the pier to warm up from the cold.

Looking at our CityPASS for inspiration we headed over to the city’s tallest building, the Willis Tower, to take in the views from its skydeck. What we didn’t factor in was that on weekends unless you arrive early, expect to wait at least 90 minutes. So we left with a plan to revisit when it opened the next morning.

The Chicago Theatre and Macy’s Santaland

The lure of the nearby iconic Chicago theatre sign was too hard to resist, and after taking the obligatory photos we called into Macy’s on State street in the heart of the theatre district.

Christmas had just arrived in store, so we got to experience the holiday windows, the magnificent tree in the Walnut room and the amazing Tiffany dome ceiling.

Even if shopping isn’t on your agenda, it’s well worth calling in here to see this stunning store.

We love choosing Christmas decorations for our tree back home and had great fun picking decorations from the Holiday Lane section of Macys.

However for Chloe and Holly the lure of Santaland was the main attraction of their Macy’s experience.

This was a fun and interactive Christmas journey as we reached the home of Santa, where they girls got to share their wishlists with him. It’s hard to beat the Santaland New York experience but Santaland at Macys Chicago store will be better than anything that you would experience at a store in the UK, apart from Harrods in London.

Dinner at Texas de Brazil

That evening we headed to Texas de Brazil for dinner. This was recommended to us when we were in Chicago and I now know why.

It was an amazing dining concept that we all loved where gauchos carve charcoal-grilled meat at your table.

This allowed the kids to try a variety of dishes and even Chloe who would typically order chicken, sampled everything from pork, beef tenderloin to leg of lamb and for me the highlight was the fillet of beef – the food here is wonderful.

We were all given a two-sided card to indicate whether the gauchos should bring more meats to the table but make sure you leave room for dessert.

There is a wide range to choose from. I had pecan pie, Ian had the Brazilian cheesecake and the girls selected their favourites – Creme Brûlée for Chloe and chocolate mousse cake for Holly. Texas de Brazil Chicago is a definite recommendation when in the city.

Day 4

Breakfast at Wildberry Pancakes

Wildberry Pancakes was a 5 minute walk from our hotel and is a must visit for breakfast. The pancakes here are some of the very best you will ever have.

The menu is extensive and our pancakes were delicious. The trouble is the pancakes are so good that you have to reserve your place in line and with a 30 minute wait we headed to nearby Maggie Daley Park until our table was ready.

Maggie Daley Park

Maggie Daley Park was one of the girls’ favourite areas of the city. If you were designing the perfect playground then this would be it, with lots of huge slides, ice skating rink, climbing walls and a giant suspension bridge – best of all it is framed by the iconic city skyline.

After a filling breakfast at Wildberry Pancakes, where we had delicious pancakes ranging from Oreo to their Signature Berry Bliss, we hailed a cab to take us to the Museum of Science and Industry, a 20 minute journey away.

The Museum of Science and Industry

The Museum of Science and Industry (included with CityPASS) is the largest science museum in the Western Hemisphere and is the most impressive museum that we have ever visited.

Highlights of your visit should include a U-505 submarine, the only German U-boat captured during World War II and experiencing what it’s like for miners by going down into a coal mine.

One of our favourite areas was Science Storms where the girls got to walk inside a 40ft tornado and learnt about how a giant Tesla coil can produce electricity; this was interactive learning at its very best and much more fun than a classroom. We also really enjoyed getting lost in the mirror maze and the amazing baby chick hatchery.

Our girls loved ToyMaker 3000, where they learnt about robotics as they watched 12 robots assemble the colourful gravitron toy that they had just designed on screen. They were both so proud of their little creations when their toy came off the production line.

There is so much to see and do here in this cavernous museum we spent nearly the full day here and still didn’t get to see everything.

Hair styling at the AG Salon

We took an Uber back to the Swissotel before heading out in the evening for some more retail therapy and Chloe and Holly had an appointment at the AG salon for their dolls to have their hair styled and ears pierced.

Cheesecake Factory

We ended the evening at one of the kids’ favourite restaurants when we visit the USA – the Cheesecake Factory located on the ground floor of the John Hancock center. I still don’t understand why they don’t have these restaurants in Britain. They would be so popular and we left happy with two celebration cheesecake slices.

Day 5

The weather started to warm up towards the end of our trip and we started the day back at Maggie Daley Park, crossing the impressive curved BP bridge designed by Frank Gehry into Millennium Park..

Millennium Park

What we loved about this 24 acre park in the heart of the city was that it offered so much green space for the kids to run around and have fun. The fabulous Pritzker Pavilion hosts outdoor concerts and the Crown Fountains must be the coolest works of public art anywhere in the world. We loved watching the faces in the two 50-foot glass block towers change.

Art Institute of Chicago

At the Art Institute of Chicago we stopped for a photo with the famous lions that guard the entrance. The girls recognised this from the 80s classic movie – Ferris Buller’s Day Off! We grabbed a quick breakfast at Starbucks opposite which provided us with amazing views of the Art Institute and the artwork of Andy Warhol.

Route 66

Chicago is home to the start of the iconic Route 66 and the road begins right next to the Starbucks where we had just had breakfast. We followed the route, taking numerous selfies and taking in more of the gorgeous architecture that is everywhere in this city on our way to the Skydeck.

Skydeck Chicago

No visit to Chicago would be complete without a visit to the Willis Tower, formerly the Sears Tower, and home to the Skydeck on the 103rd floor.

Our experience began with an interactive walk through, book where we learnt about the tallest buildings in the world, including one of our favourites the Burj Khalifa in Dubai and the history of the Willis Tower.

One of the worlds longest elevator rides whisks you at an ear popping speed to 1,353 feet to the highest building observation deck in North America.

During our visit we learnt that although the new One World Trade Center in New York is now the tallest building, its only because of its spire on the top. The Willis Tower and the Skydeck is the tallest viewing platform in the Western Hemisphere so the 360 degree views of the skyline of Chicago, the coastline and its neighbourhoods are amazing.

On a clear day, which it was when we visited, we were able to see the neighbouring states of Indiana, Michigan and Wisconsin.

The highlight of our visit to the Skydeck was ‘The Ledge’ I would highly recommend you try this once in a lifetime experience. I did and I’m really scared of heights!

There are four 4 ft glass floor balconies 1.5 inches thick that extend 1600 feet above the city below. I was so scared but the children had no such fear, especially Holly who did a handstand! – look away if you have a fear of heights.

Deep Dish Pizza at Giordano’s

For lunch we tried one of the city’s signature dishes, the deep pan pizza at Giordano’s Pizza within a 5 minute walk of the Willis Tower.

This restaurant wins awards for their creations which can take up to 45 minutes to prepare and it’s easy to see why. The deep pan cheese and tomato pizzas we had were amazing.

Garretts Popcorn

Along with pizza, when you are in Chicago you have to visit a Garrett Popcorn shop and try their famous cheese and caramel classic Chicago mix – their popcorn is so good.

Learn about the Chicago Bears on a VIP Tour of Soldier Field

Whether you are an NFL fan or not you should try to visit the historic Soldier Field home of the Chicago Bears.

Ian is a massive fan of American Football and booked us onto one of the VIP tours that run several times a week.

Our 2 hour tour was excellent and really enjoyable especially for the kids. We learnt about the history of the stadium. The highlight was being able to walk out onto the field, (Holly in particular loved it. I think she could be a future sports star)

This was an all access tour so we got to see behind the scenes in the dressing rooms, commentary boxes and the amazing views from the executive lounges where tickets start at $900 per person!

Field Museum of Chicago

Across the street from Soldier Field is the Field Museum of Chicago and was available on our CityPASS. Like the other world-class museums in Chicago, this natural history museum will be one of the very best that you will visit anywhere in the world.

Inside we made our way to the museum’s most famous resident, SUE the largest, most complete, and best-preserved Tyrannosaurus Rex ever discovered. Other highlights included being able to walk into the ancient Egyptian tomb and having a selfie with the huge Titanosaur.


We rounded off our trip with one of my favourite things to do in the USA, shopping. Chicago is a dream shopping destination with every store imaginable, so it’s perfect for shopping even with the weaker pound to dollar exchange rate!

Chicago is home to the world’s largest Ralph Lauren store much to the delight of Ian and there were some amazing deals to be had especially at Macy’s and my favourite Bath and Body Works.

All in all, Chicago has been one of our favourite trips so far. If you’re looking for a family friendly destination with plenty to keep all the family entertained, you’ll love visiting Chicago with kids.

Before our visit we found that the official online guide to Chicago was really helpful to give us inspiration and to help plan our trip so it’s well worth checking out

1 Comment
  1. You certainly experienced some of the BEST that Chicago has to offer and I’m so happy to see that you and your family has such an enjoyable time. I’m incredibly proud of “my” town and hope your readers will be inspired to visit soon. Anytime of the year. Cheers!

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