When we visited Chicago over Halloween to see friends, we had zero expectations of what to expect from the city. But to say we completely fell in love with the place is an understatement, and I think it might be our favourite city break in the US. This city was clean, connected with nature and full of incredible things to do as a family and that’s without the picture postcard suburbs and surprise sand dune beaches. If you are reading this because you have already booked a trip to Chicago, then I am so jealous and if you’re curious and not sure whether to book then I cannot recommend enough that you grab those flights and enjoy Chicago to its fullest.
Useful Tips
How to get there
The rumours are of course true in that getting through US customs can be a long drawn-out process, but Chicago O’Hare International airport is a slick operation. Arriving in the airport we had pre-registered for MPC entry, which meant our details were pre-loaded and approved and on-landing we took a picture of ourselves to upload in the app. This photo part has to be done on arrival as the approval times out within four hours. This took us to a short, fast-moving, queue which we cleared in under 15 minutes as opposed to the non MPC line which looked more like two hours long!
When to go
From Spring until Fall is Chicago’s time to shine. In the Autumn the suburbs are resplendent with golden trees and blue skies, but if you wanted to make it a proper beach and city break, head over between June-August.
How to get around
Staying in River North meant that the city was very walkable and we also found it easy and affordable to use taxi and ride apps. If you would like to expand your trip to the suburban beach towns of the North shore, take the double decker UP-N train line to Winnetka.
Where to stay
We split our time between staying with friends in the suburbs and exploring in the city centre of Chicago. Whilst we were in the city we used the chic and super affordable FOUND hotel as a base. FOUND is in the River North area of Chicago and though our family room was a no frills affair it was exactly what we needed to regroup at the end of each day of exploring. The hotel had clean and calm interiors and spacious, well decorated bathrooms. It also had a shared kitchen where you could grab take out coffee or make meals. We didn’t eat in while we were there, but it was great to store our takeout bags when American dinner portions defeated us! Found is a no-frills affair, but for around £100 a night for the three of us, it was extremely good value. If you book this hotel, I would strongly recommend asking for a room at the back of the hotel as the road outside could be quite noisy at night.
We very much only needed somewhere to sleep that was clean and comfortable on this trip due to visiting friends and knowing we would be out a lot so if you are looking for a hotel that is more than just a comfortable base I would recommend elevating your experience at Moxy which is also in River North or Citizen M.
3 day Itinerary
Day 1
Most flights from the UK will arrive around mid-afternoon to Chicago, so by the time you have navigated customs and taken the hour transfer to the city centre you will most likely just want to eat and crash out. We certainly did! We wanted to start our trip in true Chicago (town) style and actually took a recommendation for the best deep-dish pizza from our security officer at the border! Just a short-walk from our hotel was Lou Malnati’s, a local deep-dish hero where we kicked off our stay with the most delicious deep pan pizza. You could be forgiven for thinking the interiors were very ‘Pizza Hut’ but for what it lacked in aesthetic it very much made up for in taste! Jet-lag then kicked in and all three of us were super happy to see our beds that night.
Day 2
Of course, we were up bright and early for the start of our first full day and starving! So we headed to Yolk, a famous brunch joint in Chicago with various spots all over the city. We headed for the most central one in West Loop which was right on the river. Yolk gave us everything we wanted for our first American breakfast of the trip…every order came with a stack of pancakes as a side!! Suffice to say we practically rolled out of there fuelled with pancakes, syrup and bottomless coffee. This brunch spot opened super early which was great for our jet lag clocks.
Our morning activity on the first day was the famous Chicago River boat tour. We opted for the 45 minute version as sometimes keeping the attention of our five year old if he is not on the move can be challenging! The tour was exceptional and an amazing way to see the city in all its glory – it even stops briefly in Lake Michigan so that you can get a lakeside view of the whole skyline. The guides walk you through the architecture but also the history of Chicago. We sat on the top deck in the Autumn sunshine and it was one of the highlights of our whole time in Chicago. If you are on limited time would be the thing I most recommend doing.
After a nine hour flight the day before, we decided to follow the sun and spend the remainder of our day outside. We walked across town to get some photos at The Bean – the quintessential Chicago landmark and then whiled away a few hours in the incredible green spaces and playgrounds of Millennium Park.
This park was another great surprise in the city of Chicago – stretching out over nearly 25 acres – this interconnected series of green spaces delivered some of the most thoughtful children’s playgrounds we have ever come across!
Famished from our very many steps and unsettled body clocks we wanted to dive further into the best of Italian American cuisine and Il Porcellino did not disappoint. I will extol the virtues of this restaurant to anyone who will listen, not only did we dive into their towering lasagne and arm length mozzarella sticks but there was so much left over that we took the food away for lunch the next day. The wine list was also outstanding. A meal we will think about for years to come.
Day 3
Another early start for us on Day 3, and another stand out diner breakfast. The historic Lou Mitchell’s diner had been recommended to us by a friend who had visited their outpost on Route 66 and we were NOT ready for these portions. After deep fluffy omelettes, pancakes and more we barely needed to think about food for the rest of the day!! But it did fuel us up for our day of tackling the many and varied family-friendly museums that Chicago had to offer.
Starting off with the outstanding Shedd Aquarium. Positioned in Millennium Park next to the Cubs Stadium and the Field Museum, this is a museum hotspot to bookmark. On entering the Shedd, do as we were advised and head straight down to see the sharks. This begun an incredible experience of exploring marine wildlife, where we got to see Stingrays and more up close.
Due to proximity, we next made a bee-line for the Field Museum – a cavernous natural history museum that our Dinosaur lover was captivated by. As well as an extensive natural history collection, there was also a sweet (and very quiet) play space that allowed us parents to rest our weary legs for a minute! The City Pass is a really good way to save on these attractions and other must see spots like Chicago Skydeck, the River Tour and the Griffin Science Museum.
It being Halloween, we wanted to make the most of being in America and booked tickets for Jacks Pumpkin Pop Up and oh my – I WISH we had Halloween events like this in the UK! Made as a day to night event, we went for the family friendly early slot before the party got started later on. We were so glad we got the opportunity to dive into an all-American Halloween, but it did mean we had to eschew some other great museums such as the Children’s Museum and Museum of Ice Cream. Check out another amazing blog on Chicago with kids from Bridges and Balloons.
Looking to extend your stay?
One of the things that surprised and delighted us the most about Chicago were the film set-esque suburbs. Just a 40 minute train ride North of the city are the towns of Wilmette, Winnetka and Glencoe. Not only are these the famous filming locations of the Home Alone movie but quite extraordinarily they are also beach towns worthy of far more tropical locations. Bordering Lake Michigan are white sand dune beaches that provide the most amazing balance to city life. These suburbs are also home to the stunning Chicago Botanic Gardens.
If you want to experience a side of Chicago that most tourists will not I fully recommend booking an Airbnb near to Gilson Beach or Lloyd Park for an unexpectedly delightful US beak break.
That Holiday Mum x