Earlier this year our family of six packed up our suitcases, passports and a lot of excitement for a two-centre holiday that gave us the best of both worlds: a few action‑packed nights in Chicago, followed by a full week of sunshine, sand and relaxation at Iberostar Selection Paraiso Maya Suites on Mexico’s Riviera Maya.

It turned out to be one of those trips that ticked every box: culture and skyscrapers for the grown‑ups, endless fun for the kids, and plenty of time together that we will be talking about for years.

Chicago was our starting point and it set the tone brilliantly. For a family of six, it worked perfectly: big city energy, but compact enough that we could see and do a lot in just a few days. This is now my favourite US city.

We spent our time wandering along the Riverwalk, with coffee for the adults and snacks for the kids, watching the architecture rise up around us. Heading up one of the city’s famous observation decks for those jaw‑dropping views across Lake Michigan and the skyline. Grabbing classic deep‑dish pizza (messy, but a big hit with everyone). Strolling through Millennium Park to see “The Bean” and letting the kids run off some energy in the open spaces. Chicago worked really well as a family city break: easy to get around, plenty of green spaces to balance the urban feel, and lots of simple, low‑effort ways to keep everyone entertained between the “big ticket” sights. After a few full days of exploring, we were ready to swap skyscrapers for palm trees.

From Chicago we flew down to Mexico’s Caribbean coast and checked in to Iberostar Selection Paraiso Maya Suites. This was home for the next week, and it gave us exactly what we wanted after busy days in the city: space to unwind, loads for the kids to do and that lovely all‑inclusive ease that makes family holidays feel like a proper break.

Arriving at the resort, the first thing that hit us was the scale: lush gardens, wide pathways, and pools seemingly around every corner. With six of us, that sense of space really matters. We could spread out, find quieter corners when we wanted, and never felt cramped or crowded. The welcome was warm and efficient, and before long we were in our suite, bags dropped, kids into swimwear, and the pool firmly in their sights.

Travelling as a family of six, room layout is always important. The suites at the Maya gave us plenty of room so we were not living on top of each other. Comfortable beds and a good amount of storage. It felt like a proper base rather than somewhere we were just squeezing into.

The heart of our week in Mexico was very simply: water, water and more water. Between the main pools, the lazy river-style areas and the children’s waterpark, the kids were in heaven. There was always something new to try, whether that was different slides, splash zones, or just drifting and playing. For us as parents, it meant we could actually relax on a lounger, confident that everyone was happily occupied and close by. The beach was another highlight. Soft sand, warm water and enough space to build sandcastles, play games, or just sit and watch the waves. For families, having both the pool and beach so close together is a huge bonus, and we certainly made the most of it.

Feeding six people, several times a day, can be a challenge on holiday. At Iberostar Maya Suites it never felt like hard work. Across the buffet and à la carte restaurants there was always plenty of choice, which made life much easier with different tastes and appetites to cater for. From fresh fruit and simple pasta dishes for the younger ones to more adventurous options for the adults, everyone found something they looked forward to. The all‑inclusive set‑up meant we did not have to think about the bill each time someone wanted a drink, an ice cream or a snack by the pool. That freedom made the whole week feel more relaxed.

Beyond the pools and beach, there were lots of extra touches that helped make it special for the whole family. Evening entertainment so we could all sit together and end the day with a show or live music. Plenty of places just to wander, talk and enjoy being together without needing to “do” anything in particular. Some of our favourite memories are the simple ones: evening walks under warm skies, late‑night chats on the balcony once the kids were asleep, and the shared excitement of planning what to do the next day.

Looking back, this twin‑centre combination was ideal for our family. Chicago gave us culture, energy and a real sense of adventure. Iberostar Selection Paraiso Maya Suites in Mexico gave us space, sunshine and that effortless all‑inclusive comfort that makes it easy for parents and fun for children. Travelling as six can sometimes feel complicated, but this itinerary felt straightforward and rewarding at every step.