Lifestyle // Chicago Travel Diary #3 – Boozy Brunches, Baseball Games & Big Goodbyes

July 27, 2016

Drinking downtown, brunch in Boystown, Chicago Cubs at Wrigley Field, Lake Front Trail

My last Chicago Travel Diary left off on Friday afternoon, about to meet Sarah after a day of sightseeing and ready to celebrate the weekend and my friends being off work and two other baes flying in to join the party. Hold onto your butts, things are about to get boozy! (Also includes A LOT of food, excellent bars, a baseball game and an oh so candid photo shoot…)

DAY 4 CONTINUED – Friday 6th May PM 

I picked Sarah up from her office and she took me to one of her favourite drinking spots in the city – Cindy’s Rooftop Bar. It was amazing! They have a really extensive cocktail menu, cool DJ and a beautiful terrace overlooking Millennium Park where we managed to nab a space and admire the view whilst devouring our drinks. It’s a really lovely place to stop for a drink or two, and great to see The Bean and Millennium Park’s other attractions from this angle. After a few mojitos we started to feel peckish so headed down stairs where a Shake Shack is conveniently located – another reason to love Cindy’s and grabbed ourselves some tasty burgers and fries. (Side note – read my review of Shake Shack Covent Garden here). On the hunt for more booze (drink responsibly kids) Sarah then whisked us off to the Virgin Hotel Rooftop bar, Cerise. Again it was absolutely packed as office workers spilled out to celebrate the end of the working week and enjoy the amazing sunshine, but we managed again to find a table and settled in. Sarah pointed out the buildings that surrounded us, including where Al Capone used to have a prohibition bar in which cars drove in at street level and straight into a lift that took them to the top floor where the bar was held, and also my favourite building – the Carbide & Carbon Building which was modelled after a bottle of champagne. So pretty! Our view then got even prettier as our friend Hilary arrived! Cue lots of excited squeals and hugs! Hilary is another of my summer camp friends who actually masterminded this whole trip, so big big love to her, thanks HilsBils! We hadn’t seen each other for about eight years so it was incredible to be reunited and catch up on all her news over a couple of glasses of rose in the sunshine. That night we were off to a leaving party for one of Amy and Sarah’s friends who was moving to Colorado, so we headed home to spruce up before venturing out to an Irish pub in the local neighbourhood.

DAY 5 – Saturday 7th May

Feeling pretty hungover (last night’s bar was $30 all you could drink…) and now joined by Bridget (whose plane from Boston last night had been delayed, meaning she sadly arrived to a house of drunken messes chewing down on left over pizza and shovelling Cheez It’s, rather than being able to join us on the night out) But we had all weekend for fun and frollicks and we wasted no time in heading for a bottomless brunch at Taverna 750 in Boystown. This place was AMAZING and again, super cheap. For the equivalent of Β£28 you get a two course brunch, all you can drink mimosa and two luxury cocktails too. London could learn a thing or two about these prices! The food was really delicious – I opted for a spicy crab dip with scallion, bacon, sriracha and toast to start, which was incredible – really flavoursome and rich. I then moved on to scrambled egg and bacon for my main course. The restaurant itself was so buzzy and vibrant with an amazing soundtrack of perfect songs for a girlie boozy brunch – Kylie, Cindi Lauper, Lady Gaga – you name the diva, they played her! 

We then headed over to Wrigley Field where the Chicago Cubs would be playing a baseball game later that day. Whilst we didn’t have tickets to the game we wanted to go over and soak up the atmosphere, and the beer! We started off at Murphy’s Bleachers, a sports bar just across from Wrigley which was heaving with fans wearing Cubs kit. Keen to feel like a true local, I decided to buy myself a baseball cap which I wore with pride for the rest of the day (and a surprising amount since actually!) After a few rounds of beer we bit the bullet and picked up some cheap tickets from a tout and headed into the stadium. Goooooo Cubs! I’ve seen the San Francisco Giants play before and have to say baseball is not my favourite game as it just seems to go on for HOURS, but I do love the live atmosphere of any sports game. Of course we headed to the kiosk to buy some more drinks and a ton of food (what bottomless brunch?!) Lucy went all out and got the Big Slugger Nachos which were probably the best thing I’ve ever seen – heaped high and served in a blue plastic full sized replica Cubs baseball hat, which she kindly let me keep and now sits proudly on my shelf, just crying out to be filled once again with tortillas and plastic cheese! 

We found our seats and watched some of the game whilst chowing down on our nachos. It did get very cold though as we were fairly far back and covered by the bleachers above so thrown completely in the shade. After posing for a few photos by the pitch (y’know, to prove we were there – if you didn’t gram it, did it even happen?!) we decided to head back out to some bars to warm up and allow us to be a bit more sociable.

We decided to go to Sluggers, a renowned bar in Wrigleyville which has a ball cage upstairs as well as several arcade games and trampolines (none of which we went on!) The bar downstairs is great – really big with lots of big screens showing the game and fun pop music being played over the top. After a few hours of drinking and singing we decided that more food was definitely in order and we jumped in a taxi to Lou Malnati’s home to the best deep dish pizza in Chicago. YASSSSS!

Pizza is my One True Love (and Sarah, Amy, Bridget and I all originally bonded over our love of food – true story!) so I don’t know how I didn’t prioritise grabbing a slice of deep dish last time I was in town. Still, better late than never my friends! The restaurant was packed and is known as being a favourite with the locals, rather than tourist hot spot chain Giordano’s, so head to Lou’s if you’re looking for a more authentic Chicago experience. The pizza was amazing! We went for a large Cheese Deep Dish and a small Sausage Deep Dish for the table -and they were both incredible. The dough is much more like that of a pie consistency than a traditional crisp pizza base – more buttery and with a nice fried taste around the edges, from where it’s been sat in the tin pan whilst cooking. Deep dish pizzas also have the cheese and fillings layered on top of the base, with the fresh tomato sauce added, and a decadent sprinkle of Parmesan cheese to finish it off. Blimey o Reilly it was a meal and a half! You definitely only need a few slices of this to fill you up, and I’m usually a bottomless pit when it comes to pizza! I think Sarah was right when she said that traditional pizza and deep dish are so different that you have to be in the right mood for either – the craving for one would not be satisfied by a slice of the other. I think I definitely prefer traditional pizza but I’m so glad I finally experienced the famous Chicago dish and will definitely head back to Lou’s for a slice next time I’m in town. 

DAY 6 – Sunday 8th May 

Last full day in Chicago and seeing these babes wahhhh! Deciding we didn’t indulge enough yesterday (ahem) we went to Melrose Diner just around the corner for brunch. It was really cute inside, and exactly like the typical 60’s American diners you see in the movies! I picked the deliciously decadent Meat Lovers Skillet – which was basically a huge plate of hash browns with bacon, sausage, ham, onions and peppers and sunny side up eggs. Oh, and maybe a cheeky side of pancakes too! Well it had to be done didn’t it, when in Rome and all that! It was all absolutely amazing and just what I needed after yesterday’s boozy antics. I didn’t finish it all, which of course meant I didn’t feel too guilty when we then headed to Bobtail ice cream parlour! They had such a huge menu with loads of flavours, toppings, milkshakes, sundaes and shakes to choose from, it was hard to decide what to have, but in the end I went for a scoop of house special white chocolate peanut butter cup. Yep, it was amazing as it sounds!

In need of a good walk to try and counteract some of the calories we’d just eaten, we decided to follow the Lake Front Trail, which I’d walked on Wednesday (read about that here). How different the weather was! Whilst it had been freezing cold with dark and moody skies earlier in the week, the lake was now beautifully calm and reflecting bright sunny skies. Perfect! It was so lovely to see the lake at its best in the stunning weather and we stopped for many a photo opportunity as we chatted and laughed our way down to Lincoln Park. So candid! 

Feeling pretty thirsty, Amy and Sarah took us to the AMAZING rooftop bar, The J. Parker (which was possibly my favourite bar of the weekend!) It was really busy but we were soon able to grab a table and enjoyed the beautiful views out across the lake whilst listening to the great music the DJ was playing. Seriously, he even did a 15 minute Sean Paul set – I was in heaven! Surprisingly (or maybe not…!) after a few cocktails we decided to order some food – hand cut rosemary fries and pretzel sticks with beer cheese. Yep I’ve no idea what beer cheese is either, but it was absolutely bloody DELICIOUS!  Essentially we had a bowl of melted cheese with soft pretzel sticks to dunk. England seriously needs to up its bar snacks game! After a couple of hours soaking up the sun (and gorging on as much plasticy cheese as we could muster) we got a taxi back to the apartment as it was sadly time to say goodbye to Hilary and Bridget sob! 

After lots of hugs and promises of not leaving it another eight years before we all see each other again, the girls got their taxi to the airport and Sarah, Amy and I comforted ourselves the only way we knew how – eating more food of course! (Yep, I’m judging us whilst writing this, too!) We headed round the corner to Wilde, an Irish pub named after Oscar Wilde which was decorated like an old library, with Wilde’s famous quotes written everywhere. “Love and gluttony justify everything” really seemed to sum up our weekend! I chose the Knife and Fork Grilled Caesar with Buffalo Chicken, which was a deliciously grilled whole romaine lettuce with chicken strips coated in hot buffalo sauce, parmesan, croutons and drizzled with Caesar dressing. I’ve never had grilled lettuce before, but will definitely be trying to recreate this at home! The chargrilled flavour was so nice, and really made it a lot more interesting to eat had it been standard salad leaves. Feeling pretty full, and exhausted from having so much fun over the last week, we headed back to the girls’ apartment to watch our favourite episodes of Friends whilst I packed up my suitcase, ready to head home the next morning.

I literally had the most incredible week in Chicago with my friends. It was just what I needed, and a fantastic way to celebrate turning 30 – I couldn’t think of a better present than being in the presence of these girlies! Thanks for the best week darlings! I absolutely loved Chicago – it really is a very special city with so many things to see and do, beautiful scenery and friendly people (and of course, deep dish pizza!) If it’s not already on your Wanderlust List I hope my travel diaries have persuaded you that it absolutely should be. I am already plotting how and when I can go back for another visit!

What would be top of your Chicago To Do list? 

Which other American cities do you love to visit?

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I realise this was quite a boozy post, soz! To follow some more cultural exploits, check out my previous two Chicago Travel Diaries:

Chicago Travel Diary #1 – Adventure, Art & Animals

Chicago Travel Diary #2 – Scaling Skyscrapers, Tacos & Tequila and Understanding Architecture

2 comments so far.

2 responses to “Lifestyle // Chicago Travel Diary #3 – Boozy Brunches, Baseball Games & Big Goodbyes”

  1. Pam Scalfi says:

    ending a trip with friends is the best! so much good food! πŸ™‚ these shots are awesome :)Pam xo/ Pam Scalfiβ™₯

  2. Lauren Konopacz says:

    DUBLIN NEXT (/again)!

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I’m Emma – or Emsypickle!


I live in Brixton in London. I eat out far too much, am always planning my next trip and have a borderline unhealthy obsession with Harry Potter.

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