A weekend in Chicago

Chicago is an incredibly popular destination for those looking for a city break in the USA and I’ve been looking for an opportunity to go since the day we moved over to the same side of the world as the windy city. Thoughts of skyscrapers, shops, urban sophistication and the sparkly bean filled my daydreams until finally we booked a package on Expedia and we were on our way!

We kicked off our weekend in style using our 500 mile upgrades on American Airlines to shift up to First Class – our flight had been delayed but our spirits were lifted  as we enjoyed a few glasses of wine in our comfy seats, chatting to the airline crew about their top tips for the city.  500 mile upgrades cannot be used on international flights and we have so many of them, I struggle to see how we can ever get any value out of them, so using a few here was a huge bonus.

American Airlines Upgrade

Side note – the AA app has not been working to request upgrades so make sure you have requested them online when you check in or, better still, call customer service to check that you’re on the list!

Arriving at Chicago O’Hare airport, we jumped on the blue line (metro) headed downtown. For $5 a ticket this is absolutely the easiest, and most reliable way of getting from the airport into the city. A cab might be slightly quicker but you always risk getting stuck in traffic while the metro is comfortable and will take you 45 minutes to reach the loop, no matter what time of day. Thanks to the flight delays we didn’t make it to our hotel until late but the staff were amazing and we were checked in, unpacked and heading out into the city lights within 20 minutes. We grabbed a space at the bar at the consistently popular and lively Purple Pig (we’ve heard that lines for tables during peak eating times can be super long, but we got there after 10) ordered a couple of glasses of wine and watched the chefs whip up incredible looking tapas plates. We chose the deep fried, chorizo stuffed olives, the raclette plate and the house made meatballs, which won best dish hands down.

Downing the remainder of our wine we headed for bed to get a good rest, ready for 48 hours of exploring! Day one started strongly with an incredible brunch at Beatrix which has now earned a spot in my list of favourite places to eat in the world! The lemon pancakes are worth travelling to Chicago for (seriously) and the whole restaurant has a very chilled and cosy atmosphere - perfect for a chilly weekend morning. Seriously - just LOOK at these pancakes....

We toasted a few mimosas to a great start to the weekend and set off in search of some landmarks – stopping first at the famous Water Tower on Michegan Avenue. It was constructed in 1869 to house a large water pump, drawing water from Lake Michegan and it's the second-oldest water tower in the US! It's now home to local exhibitions although they're not much to write home about and quite frankly a bit random - I'd stick to admiring it from the outside! 

From there we found ourselves wandering the boutiques of Michigan Avenue and the Magnificent Mile shopping district. There is everything your shopping heart could desire along this road which is a bit like London’s Oxford Street, Bond Street and Totenham Court Road combined into one, mixing high end fashion with high street favorites and 4 storey showrooms of the best furniture retailers in North America. It’s all here and if you’re not careful, you will never leave! By the time we’d browsed through a few of the shops our stomach’s were starting to cry out again so we followed their lead in the direction of Eataly, an Italian (duh) marketplace spanning 2 floors with deli’s, restaurant counters and a cooking school – the perfect place for a snack and a glass of wine….and something sweet for the road!

Eataly is just by the Chicago River and as we were full of food we decided on a sedentary activity so we hopped on one of Windala’s architectural boat cruises. The tours are 75 minutes long – the prefect length to be informative and interesting without taking up too much time on a short trip. They leave every hour, if not more frequently and, from what I understand, rarely sell out so you can show up on the day and buy tickets - I would highly recommend one to anyone visiting Chicago.

We learned so much about the city's history and some funny tidbits about some of the local celebrities while we gawped at the varied skyline. The mix of old and new, clever architecture is really something worth taking some time over. There’s a bar on board so you can drink while you think but make sure you wrap up warm because you’ll want to sit out on the open top deck for the best views and it gets rather chilly! Although this skyline is worth a few shivers if you ask me.

Chicago skyline

Brunch, lunch, a boat tour and some fancy boutiques was just about enough to fill our first day so we scuttled back to the hotel to defrost over some cocktails at the Commons Club Happy Hour where guests drink for free between 7 and 8pm - mega perk! After which you have enough time to freshen up and head back out into the buzzing streets for dinner. One of the things I loved about Chicago was it's European approach to mealtimes. Our dinner reservations varied between 9pm and 10:30pm and all of the restaurants we ate at were still seating guests at midnight! The relaxed attitude made our days feel long and relaxed, quite the opposite of what were surprised to experience in Sydney, where we had to rush from sightseeing all day to make dinner before kitchens closed at 9 and left us scoffing our plates in empty restaurants while waiters tidied up around us, willing us to leave so they could go home!

Our second day began with a good old Sunday lie in before the sun streaming in through the windows eventually won it's battle and convinced us to go outside and play, so we set off for Millennium Park. We got shamefully lost along the way and in a panicked attempt to find a map and directions, we stumbled across the Athletic Association hotel. Their rooftop restaurant, Cindy's, was on my radar and had been recommended by a friend, but I'd dismissed it on the basis that we'd never get a table (they don't take reservations for groups smaller than 6 people). As we were passing I figured we might as well give it a shot and our luck was in - there just happened to be a little spot at the bar so we grabbed it and settled in for a quick breakfast!

Taking (necessary) regular breaks to check out the view for the amazing terrace overlooking the park.

Keen to work off our little "sandwich" we left the restaurant and hit ground level to check out the park and surrounding area from another angle.

We didn't hang around though as we had tickets for some of the hottest seats in town at the Cubs game! Baseball is in the life blood of the people of Chicago and I'd hasten a guess that 25% of the people I passed on that Sunday were wearing at least one item of Chicago Cubs branded clothing! From the moment you arrive at Wirggleyfield, you know exactly why you are there.

Wriggleyfield Chicago

We were treated to some incredible seats by our hosts for the afternoon who also, luckily for us, knew the rules of baseball! As we sat in the sun enjoying a few beers I was once again surprised by how much I loved watching another sport live that I'd previously passed off as "boring" or quite frankly, just ridiculous! Although low scoring the game was very close and exciting to watch until the final ball had been pitched.

If you are planning a trip to Chicago and the Cubs are playing at home, do yourself a favour and make sure you leave time to go to the game. You can pick tickets up online or just find a tout on the day, and if for some reason you can't get inside the ground, there are also countless rooftop bars surrounding the stadium that have seats mounted on them so you can watch the game as if you're part of the stands! It's truly unique and very, very cool. The whole district of Wriggleyfield is really fun with plenty of bars and restaurants for fans to spill out into before and after the game. I loved it and if we go back, I will be going to see another game. And investing in some Cubs gear :)

We made it back downtown just in time for sunset and a quick trip up to the viewing deck of the John Hancock Building where you get an epic view across the city, well worth the $20 entry fee. If you have more time you can queue up for the Signature Lounge bar which is on the next floor up and spend your entrance fee on a cocktail instead, but the wait was too long for our tight schedule.

And so as the sun dipped behind the buildings our trip to Chicago was almost at an end. But not before one last adventure. More on that to come....












Chicago travel guide