Long weekend in Chicago

Long weekend in Chicago

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Earlier this month Ollie and I escaped on a lovely long weekend in Chicago – BABY FREE!!! The whole reason for the trip was because Ollie had a spot to take part in the Chicago Marathon combined with a generous offer of along weekend of childcare from the mother in law and it didn’t take us much thought to book those flight and start planning our Chicago adventure.

weekend in Chicago
A weekend in Chicago

When did we go

We went early October and the weather was definitely turning from end of Summer (the week before we went it had been mid twenties…) to Autumn time. Which feels close to winter in the UK but I know not anywhere near as extreme as a mid west winter gets. The weather wasn’t bad but definitely a case for layers and a decent coat.

Getting there

We flew with British Airways direct from Heathrow to Chicago, as it was just the two of us flying we did something very special and upgraded our flights which really did set the trip off to a special start. I may now have ruined travel for myself going forward as it really was such a good experience I’m going to miss it when travelling as we normally do! The experience of the First class check in at Heathrow Terminal 5 and the Concorde Lounge just takes all the stress and hassle out of the start of a journey and makes a trip away feel even more exciting. We also pre-booked to use the Elemis Spa to have mini treatments before we took off. All in all, I couldn’t have wished for a better way to start the trip.

weekend in Chicago
weekend in Chicago

Where did we stay?

We booked to stay at the Chicago Athletic Association Hotel*, the location was just perfect for the marathon as it was right across from the starting area in Millenium Park. We had a view of the Chicago Bean from our hotel window. I chose the hotel as I’d previously read lovely things about it and knew the location worked. I also knew it had some great food options within the hotel as Cindy’s was a recommendation that came up time and time again.

Chicago Athletic Association Hotel

Overall, for location I couldn’t fault the hotel. But there were a few things about the hotel that I didn’t love. Within the room there’s a lack of plug sockets and mirrors so doing things like drying hair was trickier than maybe it should have been. There was quite a lot of street noise from our fifth floor room and the entrance area felt very public (there’s a Shake Shack and a coffee shop there) so did make me wonder about security a little.

However the room was stylish and the bed really comfortable and I love the athletic touches like the gymnastic bench as the end of the bed stool etc. The building is full of history and Cindy’s on the rooftop is well worth a visit too.

weekend in Chicago
Marathon morning sunrise view from our hotel room

Getting about in Chicago

We booked a taxi to collect us from the airport and take us to the hotel and had planned to just use taxis to get around. But we ended up defaulting to using Uber or walking as found taxis harder to find (which we think was largely down to the location of our hotel being so close to all the marathon activity). I used the L on marathon day to get up to China town to cheer on from there and it was really easy to navigate so wouldn’t hesitate to use that if we go back. But having Uber/Lyft on your phone comes in really handy and we found that easiest way to get around.

Things to do

One of my favourite things to do when on a city break holiday is to simply wander around. Explore the area around the hotel or venture out to new neighbourhoods to see what there is to see or do there. This is largely what we did, although on the pre-marathon days walking miles wasn’t on the cards as much as it would be normally and post marathon it was more of a slow hobble (for one of us…)

Shopping is pretty ace in Chicago too – as the centre is fairly small there’s a huge selection of big name stores (plenty of Sephoras… ) in a small area (the Magnificent Mile). We didn’t venture to other neighbourhoods for shopping but I’m sure if more independent brands is your thing then this would be a great thing to explore.

The number one thing I would really strongly recommend everyone do who visits Chicago is the Architecture Boat Tour. I found this absolutely fascinating, loved every moment of it and there were so many interesting buildings with stories galore to be told. I felt like I learnt a lot and really got to know the city and it’s history a little more in just a couple of hours.

Places to eat

Now I’m splitting this into two sections because in Chicago the deep dish pizza needs it’s own category. So if you want specifically pizza related points then scroll on. However, we didn’t *just* eat pizza so have a few more suggestions to share.

Ollie and I both love our food so we had done a fair amount of research and pre-planned a few places we wanted to try. One of my favourite things about Chicago is how it really is a foodie city, for all tastes. With the perfect mix from high end fine dining to down and dirty gooey pizzas and beefy hotdogs… and cheese fries….oh the cheese fries.


Portillos: For Chicago signature hot dogs and dirty-but-in-a-good-way food (beef hotdogs, cheese fries and shakes) this was the post-marathon stop and it was PERFECT.

Spiaggia: Upmarket Italian famous for both the Truffle Gnocchi and the fact the Obamas apparently go there. I can’t confirm any Obama spotting but I can confirm the Gnocchi is a very rich delicious plate of creamy goodness.

Acadia: A two Michelin star restaurant we booked to go to on our first night in the city. A 10 course tasting menu was a stretch on jet lag but beyond worth working through. A incredible meal of truly phenomenal food.

weekend in Chicago

Cindy’s: The bar/restaurant on the rooftop of the hotel we stayed at. The food was good but the real wow is the view. We went for dinner but if we went again I’d have to go for brunch as that’s apparently pretty epic.

Little Goat Diner: Another one I got on recommendation and it was well worth an adventure out of the downtown area. If there’s one thing I am a sucker for in America, it’s an American Diner breakfast. So there was no way I was having a weekend in Chicago without my own dose of pancake goodness.

This place is like a kitchy cool updated version of a diner with a menu of traditional diner food with a twist. I stuck with my favourite pancakes and Ollie had their fried chicken waffle. He was iffy about chicken for breakfast but then tasted it and SOLD.

weekend in Chicago
Brunch at Little Goat Diner
weekend in Chicago

The Pizza

Ok, so if you think Chicago and don’t think pizza then you’re a more cultured person than me. The signature Chicago deep dish is the thing of legend and when you’re going to visit a city famous for a certain dish then you do it right. On doing our research into where to get the ultimate deep dish Chicago pizza and without fail one of two names came up. So we did what was the only option to bring a true pizza review. We tried both.


For both pizza options they have multiple locations around the city and we opted for one just off Millenial Park which was mega busy. If eating at Giordanos be prepared for a wait. The pizza itself takes nearly an hour to cook and there’s often a line outside waiting for a table. It’s the norm to pre-order your food so when you sit down you won’t have another wait for it to arrive.

weekend in Chicago
Chicago Deep Dish – Giordanos

But what about the Pizza? It was pretty phenomenal. Gooey, cheesy. Crispy deep base. We had a combination of meatball, pepperoni and cheese with garlic. I have to say I highly recommend the garlic addition. SO GOOD.

Lou Manalti’s

Lou Manalti’s was the other name that repeatedly came up. A new location has just opened up really close to the river downtown but it only opened the day we were leaving but looked really cool. I loved the base of the Lou Manalti’s pizza as it was crispier than the base from Giordaos.

weekend in Chicago
Chicago Deep Dish – Lou Manalti’s

My overall recommendation for pizza in Chicago? Try both. I’d say the filling and the Giordanos filling was my favourite but the atmosphere and base at Lou Manalti’s was better. So the decision between the two is a hard one to make. All I can suggest is try both!

Apparently Uno Pizzeria is also worth a try… so if we go back I’ll have to explore more pizza experiences. I know, I’m selfless and just willing to take one for the team…

A weekend in Chicago…

Chicago is a great city, loads to do and amazing food to try, definitely one I’d love to visit again. Except not in January or February as the weather sounds horrific then… but I’d definitely go back. Overall I’d describe it as a like a smaller, cleaner alternative to New York.

For more information on things to do/places to eat/where to stay for a weekend in Chicago see: Trip Advisor/Chicago*

For more travel posts: A beauty junkie in London on Travel


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