Welcome to my documentation of  places I'm wandering & things I'm pondering. 

Stuck in Chicago

Stuck in Chicago

I really didn’t expect to be typing up a blog post about my time in Chicago right now! I wasn't even supposed to spend a night there - just a couple of hours in a music venue before getting back on the road with the band I was touring with. But as the band van departed for Detroit, myself, my luggage and my emotional baggage were stuck in Chicago.

I won’t go into the ins and outs of why it was decided that I’d be leaving tour that day but basically, I had no purpose on the tour. I was pretty much a tag along and everything I did frustrated someone in the band in one way or another. We were all living in such close quarters and touring is tough. I could say that it was a mixture of me asking for dry shampoo when we were running late to a show, answering a few FaceTime calls here and there and wandering off to explore on my own - but it goes much deeper than that so, for times sake, I won’t go into it.

It was 11pm. My eyes were red and swollen from a steady pre-menstrual, sleepless set of tears but my gut was tight with an almost-excited type of adrenaline. I was doing it. I was in an Uber and leaving the safety of the tour for the unknown. I was with Levi, a guy who I did a couple of classes with in uni. In true Ella style, he was having a whole new level of friendship forced upon him! I invited Levi to the show that night, got him and one of his friend names’ on the door and then greeted them at the show with puffy eyes and a flurry of fanatic drama. I asked Levi if I could sleep on his couch for a few days and he said “don’t be ridiculous, Ella! You can have my bed and I’ll go stay with a friend!”. I am eternally grateful!

While Chicago may be the start of Route 66, which ends up in Santa Monica in Los Angeles (where I live) my journey home was not a clearly mapped out road. In fact, I had absolutely no idea how I’d get home because prices of flights were at $700 each for the next week. I didn’t have enough money to stay in Chicago that long either. The day after leaving tour, I got a call from my friend, Andrea, back in LA. We had only hung out probably three or four times before my life took this crazy little turn but she was one of the first to swoop in and help me out. She said that three of her best friends lived in Chicago and she set me up, staying with them until the prices of flights back to Los Angeles dropped a little bit. So, here I was - stuck in Chicago. All up, I spent a week in the Windy City and, oh my, I was blown away!

Located on the shores of the sparkling Lake Michigan, Chicago has it all; impressive architecture, unforgettable food, and masses of entertainment. From its early days as a trading post for fur in the 1800s, Chicago has progressed to become the third most populous city in the U.S. and a booming hub for finance, tourism, culture and the arts. Between the towering skyscrapers, the city is truly alive and packed full of awesome architecture, innovation, cool people and a feeling of festivity. While my stay here may have been unexpected, I'm sure glad I stuck around for a while. It isn't the kind of city you want to just pass through and I had a better time exploring the sun-soaked streets than I would have if I were trapped in the tour van, anyway!

Here’s a little bit of what I got up to in one of my new favourite cities during what could have been one of the best weeks of my entire life:


Locals may tell you that this is a tourist trap but in the summer, there is so much going on in the park that you’d be silly to scoff at it! Check out Cloud Gate, affectionately nicknamed “The Bean” to see the city from a new perspective - reflected in this massive metal sculpture. It’s pretty much always swarmed with tourists, so I’d recommend getting there early in the morning and then moving on to take in everything else the park has to offer. Between the lovely landscape design, innovate installation art and awesome architecture, you’ll find plenty of activities and events, which are usually free and always a tonne of fun!


The city’s recently added River Walk spans between Lake Street and Lake Shore on the south bank of the Chicago River. It features wide pedestrian paths and brilliant bars and restaurants, which sprawl onto the sidewalk. It’s the perfect way to spend a summer afternoon strolling or sipping a glass of wine, taking in the architecture, history and beauty of the area. You could rent a bike, or even a boat if you want, too!


There are so many museums and cultural things that I want to check out in Chicago but the weather was just so dang good and all I wanted to do was be outside! I know I’ll be back one day to see a show at this iconic theatre but this trip I just walked past and admired the sign. 



When I found myself alone in the streets of Chicago, the night after escaping tour, I had no idea what to see or do. My stomach rumbled and as much as I wanted to go and find a deep dish pizza, it was far too early for that! So, I headed to the one food place in Chicago that I knew was good - a donut place recommended by a new friend I made in Minneapolis, the day before.


This cosmopolitan strip on Michigan Avenue (between the Michigan Avenue Bridge and Oak Street) is Chicago’s premier shopping destination. Here, the remains of an old water tower and pumping station, which were burned in the Great Chicago Fire of 1871, stand between high-end brands and mega malls ready to burn through your bank account! Those in need of some serious retail therapy could spend hours on hour here. As for me, I just quickly wandered through and window-shopped because I was already broke and stuck in Chicago with my life up in flames!


My life is insanely ironic. It was the morning after leaving tour and I had not slept after thinking “Well, what the heck now?” all night. I was desperately in need of a coffee so I asked my mate from Minnesota and he led me to The Allis. I sipped my iced Americano on a velvet couch beneath an elaborate chandelier at this pretty and proper café and just stopped to take the world in for a while. I noticed people heading to a desk and going up an elevator so I asked the person who was sitting alone on the table next to me if he knew where they were going. He told me that it was a SoHo House. Living in Los Angeles, I knew exactly what that was - an exclusive members-only club that I should never be allowed to enter in my entire life. Sure enough, this guy was a member and let me up as a guest!! My day was made. Actually, my entire life was made, when I got up there and was greeted with a “hi” from Chance the Rapper - Chance the Mother Freaking Rapper! You’re not allowed to take photos up there, so I put my phone away and just mingled. Sure enough, I managed to meet enough people up there to be let in three days in a row! I guess that’s the plus side to being stuck in a city where you know no one, so you're forced to go out and make friends on your own!


As my stomach rumbled and I realised that I’d skipped lunch, I was lured down this beautiful brick-paved side alley in the West Loop. It was a combination of the scent of house-smoked meats and twinkling fairy lights that drew me in but I’m sure glad I decided to park up on a picnic bench and stay a while. I chowed down on some backyard Texas barbecue with a side of life-changingly delicious frito pie on my own and just sat and took in the atmosphere that felt like a mix between lunch in the school playground and a happening warehouse party!


 I loved exploring the colourful streets of this eclectic East Lakeview neighbourhood, where Levi lives. The tree-lined streets of Chicago’s “gaybourhood” in are home to funky coffee shops, groovy record stores, and a rainbow of dining options. It is also right on the edge of Lake Michigan, which made for some pretty spectacular sunset runs.


Food lovers, like myself, can't visit Chicago without tucking into a few slices of their famous deep-dish pizza, stick to the no-frills pizzerias that are scattered on every street as there really isn't a bad option among them. To express my utmost appreciation for a Levi and the fact that he quite literally saved my life, I wanted to take him out to dinner. As a first-timer in Chicago, Levi insisted that I try the city’s iconic deep dish pizza. Apparently, when it comes to who makes this Chicago classic the best, the rivalry between two establishments (Giordano’s and Lou Malnati’s) runs as deep as the crusts of the pizzas themselves. Levi’s local was Giordano’s, so we headed over and ordered the Chicago Classic. We washed the mushrooms, pepperoni, green peppers, rich tomato sauce and cheese (soooooooo much cheese!) down with a pint of 312 Urban Wheat Ale. Call it emotional eating if you want to but between the two of us, we managed to finish an entire large pie!


The summer months are pumping at this popular city beach where people come sunbathe, challenge one another beach volleyball and take a dip in the deep blue waters of Lake Michigan. Unlike Freshwater Beach in Sydney, where I grew up - this lakeside beach near the heart of Downtown Chicago actually has fresh water! However, the expansive blue horizon makes it feel like you’re by the ocean. You could literally come down from an office tower on your lunch break, swim and not be salty when you return to your desk! I always said that I couldn’t live anywhere that wasn’t by the ocean but as I rode a bike around the lake's edge and observed the surprising “beachiness” of this Midwestern city, I may have changed my mind a little.


This central neighbourhood is a breath of fresh air, right below the city’s skyline. Here, you’ll be able to wander down the Nature Boardwalk, birdwatch by the tranquil waters of North Pond or the Alfred Caldwell Lily Pool and visit the Lincoln Park Zoo, which is one of the oldest zoos in the country and, best of all, free! After exploring the park, there are a bunch of great bars and restaurants in the neighbourhood. I obsessed over J.Parker - the rooftop bar at Hotel Lincoln.


If I didn’t already have a pizza hangover from deep-dish Giordano’s the night before, lunchtime had me in the fairy light lit outdoor courtyard of this seriously cool bar, which serves delicious pizza. Don’t get me wrong, the food here is good but I came here on my own and left with a hoard of new friends because the crowd here was just so lovely and the place has a highly-social atmosphere. It also worked in my favour that when people asked, “So, what are you doing in Chicago?” My answer was, “You know, just got kicked off touring with a band”.


With vibrant vintage stores, pretty little boutiques and great places to grab a drink or a bite to eat - this is one of the hippest neighbourhoods and a hub of creativity. Exploring this area doesn’t just make for a great day out but a great night out too! There are Michelin-star restaurants, marvellous mixologists, gorgeous galleries, a thriving live music scene and pumping nightlife.


People stay through the Chicago winter to enjoy the summer. As soon as the temperatures start to reach new heights, so too do Chicagoans - with a drink in hand at one of the city’s vibey rooftop bars. The bars are not only a great place to see the city but to meet the people who inhabit it. I concluded that people from Chicago are cool but they don’t talk about how cool they are, like people in L.A. do, which makes them even cooler! I hopped between spots to mix, mingle and sip margaritas in the Chicago sunshine. The first rooftop I checked out was RAISED an Urban Rooftop Bar by the edge of the river on the third floor of One West Upper Wacker in the Renaissance Chicago Downtown Hotel. Next stop was Cindy’s Rooftop at the top of the Chicago Athletic Association Hotel, which has a fabulous view of Millennium Park, Cloud Gate, Lake Michigan and beyond. The LondonHouse is a luxury lifestyle hotel in a historical 1920’s highrise and the view from the bar on the 22nd floor is insane. From the classical architecture of the rooftop, you can look out over the Chicago River, Lake Michigan and Magnificent Mile. And of course, there was the J.Parker, 13 floors high, atop of Hotel Lincoln, with views across the park and out to the lake.



After leaving Levi’s house, I dropped my bags at Andrea’s friends’ house and quickly met Olivia. She was super sweet but had no time to hang because she had to go to work but she gave me a time and a place to meet for dinner. Let’s just say I had no idea what I was in for when I got to this restaurant in the Fulton River District. Olivia didn’t just treat me to the most delicious three-course dinner and cotton candy cocktails but we got to watch a live samba performance as we ate. This restaurant made me seriously reminiscent of Carnaval in Rio de Janeiro but equally as excited to be in Chicago in that very moment. The night was a blast, the food was heavenly and the atmosphere was electric.


It’s kind of ironic that I got stranded in Chicago with no plan, no money and no friends and ended up parting on the lake with people who I now want in my life forever! Olivia and her roommate Amanda were invited to a private boat party and they extended the invite to me too. We had the best time anchored in this panoramic party spot near Navy Pier as the sun shone on the city’s skyline. This was the perfect way to welcome the summer after two the consecutive winters I’d had moving hemispheres! I’ll trade a stuffy van for a beautiful boat any day!



When I thought of Chicago, I thought of a cool but cold city where not much goes on so getting unexpectedly dropped here in the middle of the summer was a shock to the system! Between March and September, there are over 200 shindigs that unfold around the city. I was there on the first weekend of June, which is when the annual Do Division Street Fest is held. Division Street in West Town Chicago was blocked off between Damen and Leavitt and people poured in to enjoy the live music and DJs, local brands and vendors, live runway fashion shows and insane street food (hello, lobster mac and cheese balls!). Levi, my new friends and I had such a blast at the festival that we went two days in a row!


Boats and boujie bars are a great way to take in the sweeping views of the Windy City. If you’re after chilled out way to see the skyline then you can’t beat sitting in Grant Park on a sunny day. You can pack a picnic, throw a frisbee and you won't need to pull out your ID, leave a tip or engage in small talk with strangers. The best part is - it’s free!


Unlike the $1 dirty (but delicious) dogs on the streets of New York, a Chicago-style dog is a beef frank in a seeded bun, drizzled with yellow mustard and topped with chopped onions, tomato slices, pickles, relish and a hint of celery salt. To get the ultimate Chicago hot dog experience, I headed to Weiner’s Circle where my order was taken by a foul-mouthed server, who hurled an insult at every customer in the long line. Mine was too explicit to post but my hungry belly was in stitches before I even got my hands on my food. Maybe Chicago dogs are dirtier than I thought!


Stretching 3300 feet into Lake Michigan, this fun-filled pier is a Chicago icon and it truly comes alive in the summer months. The pier was built in 1914 and pilot and navy training took place here from 1942-1945. Around 200 WWII planes are wrecked at the bottom of Lake Michigan as a result of this training. In the late ’90s, the pier began its metamorphosis into Chicago’s playground and one of its top tourist attractions. There are thrilling attractions, a 150-foot high Ferris wheel, and fireworks on summer nights. The pier boasts free admission and fun for all ages.


While I wasn’t too phased about doing all of the shows and cultural things in Chicago because the weather was so glorious, I wanted to get in some giggles at the most influential comedy theatre in the world. It opened its doors in 1959 and hosts a range of sketch comedy and improvisation shows. While they do have a Second City back home in Hollywood, I couldn’t resist spending a night in stitches. 


The summer air was scented with the sweet smell of chocolate, luring me into this Downtown factory, which was established in 1939. I am such a sweet-tooth, so I stocked up on goodies at the factory store to get me through the days of exploring.



I made a friend called Austin in Chicago who gave me some city-seeing tips. The best one he gave me was to book a table for one at this popular bar through Open Table to skip the line and enjoy some sweeping views of the city. For just the cost of an overpriced drink or a snack, you’ll be able to look out over the lake and the loop from the 96th floor of the John Hancock Centre. Just one storey below the bar is the upscale Signature Room restaurant, which offers similarly stunning views. SO, whether you want to sit down for a decadent meal or grab a quick drink, you don't want to miss "The Top of the 'Cock"!



It doesn’t matter which city I’m in, I somehow always end up gravitating to the markets. There is something about a collection of locals who are passionate about what they make, pick or produce that just makes me so happy. In Chicago, I checked out the fresh food and flowers at Logan Square Farmers’ Market, discovered the downtown Green Square Market and people watched at the eclectic Maxwell Street Market.

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