It takes a special kind of city to make you feel at home almost immediately. There aren’t many that have ticked that box during my years of travelling, but in Chicago I found a home away from home. Perhaps it was because it reminded me a lot of Melbourne. It’s very liveable, with great food, lots of cool individual neighbourhoods, and arty with strong cultural veins that give the city its lifeblood. The people were so friendly that I was taken aback at times. They really seemed to want to help me out so that I saw what they see in their amazing city. And I did. From the gangland prohibition era to the rich multiculturalism of the city’s immigrant populations, Chicago really stole my heart for a couple of days in April.
Here’s my rundown on what you can fit into 48(ish) hours in the Windy City. (Times unaccounted for probably mean I was napping or rewatching The Untouchables. More on that in a separate post coming soon.)
48 hours in Chicago: Itinerary Snapshot (more detail below)
Thursday evening: Famous pizza, shopping strip stroll and sleep
Friday morning: Big brunch, Millennium Park and public art
Friday afternoon: Self-guided architectural walk and Art Institute of Chicago
Friday night: Jazz at the Green Mill, Al Capone’s old gin house
Saturday morning: Lincoln Park and Zoo, North Avenue Beach and Lake Michigan
Saturday afternoon: Eating and shopping in trendy Wicker Park
Saturday night: Ribs at Rokit

Deep dish pizza at Giordano's
Thursday, 5pm – Deep dish and dreams
After more than 14 hours travelling from London, the only things on our minds were comfort food, some fresh air and an early night. We got lucky on all counts.
Hotel: We chose Hotel Felix – a friendly boutique eco-hotel – which was both affordable (for Chicago) and in a great location, whether you want to explore the north or south of the city.
Dinner: Chicago is famous for ‘deep dish’ pizzas (imagine a deep, bready quiche shell rammed with pizza toppings) and it just so happened we were a couple of minutes walk from Giordano’s, a Chicago institution. We managed to eat just a third of the smallest size pizza plus a salad, so definitely err on the side of caution when ordering! Boy was it good, but we haven’t been able to look at cheese since.
Stroll: While we waited for our table we took a walk in the sun down the Magnificent Mile, the part of Michigan Ave lined with the city’s upmarket shops. But it was the magnificent tulips that stole the attention. Spring in Chicago, we quickly discovered, means thousands upon thousands of tulips.

Yolk cafe, Chicago
Friday, 10am – Yolk folk
If you’re a brunch fan, then you’ll love Chicago. Being from Melbourne, brunch is a much-loved and respected eating tradition in its own right, but when you’re travelling and need to watch the pennies it comes into its own as one meal that replaces two. Chicago offers a plethora of options, with some dedicated specifically to brunch.
We fell in love with Yolk. Be prepared to queue on weekends, but we swanned in on a Friday morning and blew a few brain cells trying to decide what to order from probably the best breakfast/brunch menu I’ve ever seen. We opted for one of the famous omelettes (the Garden Delight) and a Countryside skillet, both of which were huge and delicious. Just in case you need more food (pah!), everything comes with your choice of fruit and toast, pancakes or English muffins (I’m not joking). Man the Americans can eat. And so can I, it seems. I scoffed the fruit and the rest, and returned the next day for more. I also loved the fresh-squeezed strawberry-orange juice.

Anish Kapoor's Cloud Gate, Chicago
Friday, 11.30am – Public art park (aka Millennium Park)
In the heart of downtown Chicago lies Millennium Park, bursting with the gifts of public sculpture. I was in awe of Anish Kapoor’s Cloud Gate masterpiece – also known as the Bean – which is perfect for clever reflective photography and general pondering. You’ll also find Frank Gehry’s 120 ft-high Pritzker Pavilion and Jaume Plensa’s fantastic 50ft-high fountain displaying larger-than-life video images of locals’ faces. If you’re there in summer, you can do tai-chi, yoga, pilates or dance classes in the park for free on Saturdays.
Friday, 1pm – Architectural ambling
Chicago is a paradise for architecture and design nerds. Home to the tallest building in the US and responsible for the world’s first skyscraper, even those people spoilt by Europe’s big cities and beautiful buildings would be hard-pressed not to be impressed by Chicago’s architecture and skyscraper smorgasbord. We decided to do a self-guided walking tour to see the sights and walk off brunch. Do it yourself, try the free tours by Chicago Greeter or InstaGreeter, or download a free audio tour by the Chicago Tourism Office. We did a recommended route by Lonely Planet and took in Tribune Tower, the Wrigley Building, Willis Tower (tallest building), the Rookery, and the 1930s art-deco delight the Chicago Board of Trade, ending at the Art Institute of Chicago.

Wrigley Building, Chicago
Friday, 3pm – Art art art
As a bit of an art history buff, I couldn’t resist the opportunity to explore America’s second-largest museum, the Art Institute. I was lured by the thought of seeing Seurat’s pointillist triumph A Sunday Afternoon on the Island of La Grande Jatte in the flesh and Grant Wood’s American Gothic. It’s open late on Thursday nights until 8pm.
Friday, 8pm – Nudging Capone
To get a hit of Chicago’s prohibition past and its deep history of jazz and blues all in one go, we hit the Green Mill. This jazz club was a favourite speakeasy of Al Capone but still packs a mean punch attracting top musicians and a renowned poetry slam on Sundays. Buddy Guy’s Legends also came highly recommended for blues, Southern food and a great night out.
Saturday, 11am – Lions and tigers and bears, oh my
The sprawling Lincoln Park was alive with people relishing the warm weather (as you would after a harsh six-month winter) and is a great place to hire bikes, go for a run or stroll and check out the other attractions in the area. Lincoln Park Zoo is free and home to lots of exotic species, and the North Avenue Beach is a great urban spot for eating, drinking and lounging.

Jaume Plensa's Crown Fountain, Millennium Park, Chicago
Saturday, 1pm – Neighbourhood chic
Chicago doesn’t have one beating heart, but is composed of a myriad of different neighbourhoods. With their diverse identities and cultures, they are a key part of what makes the city feel like home. We walked a solid 45-minutes from Lincoln Park through the picturesque Old Town (so named after the Great Fire of 1871) to the trendy Wicker Park. Once a working-class immigrant hub, it’s now packed with restaurants, bars, galleries and boutiques and felt very much like Melbourne’s Brunswick St. We took a break from meat and fries by lunching at the delightfully hippyish Native Foods Cafe. Its hot chai, salads, health bowls, burgers and wraps dragged us back to health and were excellent – try the Moroccan Bowl and the Ebel’s weiss beer. As an alternative, try the Storefront Company for weekend brunch or The Southern for outdoor cocktails and bites inspired by the south.
Saturday, 7pm – Ribbing it with the locals
At the last minute, we found out some friends were in town for the night. On the spur of the moment we stumbled onto Rokit Bar and Grill without a reservation. With a more sophisticated dining space downstairs and a first-in-first-served eatery upstairs that mixes drinking and dining, it was quite a good find. Excellent ribs, pulled pork, coleslaw and pork chops, plus attentive waiting staff, impressed us. A heady crowd of locals playing snooker and watching ice hockey made us feel in the thick of it. Atmospheric and loud, I wouldn’t go for a romantic dinner but it was a nice spot for a random night of eating and drinking (and being entertained by the disproportionately high number of hen parties!).