(Last Updated On: June 13, 2021)

Spending 3 days in Chicago was one of the best times of my travelling life. The Illinois capital city is full of amazing surprises in the form of gorgeous architecture, galleries, museums, jazz bars and amazing food. I visited in February, so it was super cold, but that was all part of the magic of exploring this spectacular metropolis at this time of year.

It’s the first time I’ve ever been in an urban area and experienced it snowing, so for this Aussie girl it was quite a remarkable thing to see. To help you fall as in love with this unique city as I did, I’ve compiled a list of the best way to spend three days in Chicago.

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Where to stay in Chicago

Chicago is a huge city with no end of options for accommodation. I loved staying at the W on Lake Shore which offered incrediblew views over the frozen Lake Michigan on one side and the beautiful architecture of the city on the other.

Staying around the Loop area or the Magnificent Mile are great options to be centrally located.

3 Days in Chicago

Day One

Coffee at Dollop Coffee Co.

There’s no better way to begin our three days in Chicago than with a piping hot coffee. Dollop Coffee Co. are a great chain in Chicago serving up decent lattes. When its winter in this city, a good coffee place nearby is important so you can escape the chill and warm up by wrapping your hands around a hot cup of java. I stayed out near Lakeshore at the W, and there’s a Dollop Coffee Co. about two blocks away. 

Three Days In Chicago - Emma Jane Explores

Millennium Park

Chicago’s most iconic sight in modern times would have to be the famous Cloud Gate sculpture, or as its more affectionately known, The Bean. Since it was woven into the fabric of Chicago’s charm in 2006, this work of modern art by Sir Anish Kapoor has become a favourite photo spot for tourists and locals alike. Millennium Park is a wonderful space to take in the Chicago skyline and enjoy the architecture that has made this city one of America’s most beautiful.

And the park’s beauty doesn’t stop at the Cloud Gate, either. The Crown Fountain which is also located in the park, arguably, is even more fascinating than The Bean, with two pillars at either end of a reflecting pool which display video of socially and ethnically diverse Chicagoans. It’s truly a work of interactive modern art that represents the diversity at the heart of Chicago.



Deep Dish Pizza at Giordano’s

Giordano’s is a Chicago institution and if you’re looking to experience the Chicago Deep Dish Pizza, then finding your nearest Giordano’s restaurant is the best way to experience a tried and true interpretation of the famous dish. Lunch is a good time to go, because they seem to offer a lunch special with a smaller size pizza – this helps because the full size ones are HUGE and you need a few people to really make a dent in them. The lunch deal is cheaper and you get a mini pizza (still big) and a side salad, soup or fries to go with it. You can’t spend 3 days in Chicago without trying one of these!

Chicago Cultural Center

There’s few spots in Chicago to see amazing Beaux Arts buildings more beautiful than the Chicago Cultural Center. Built in 1893, the center’s gorgeous, decorative interior is truly breathtakingly decadent. High glass domes let in natural light and hanging lamps complete the warm glow inside the building. A visit to the Cultural Center is totally free and there are usually exhibitions in the upper galleries that travellers and locals alike can roam around and mull over. The Chicago Cultural Center is right opposite Millennium Park, so it’s only a short walk from  where you’ve been exploring this morning. 


See a Show

Chicago has a brilliant theatre district, so why not experience a Broadway-quality show for (usually) a cheaper price. I surprised Matt with a ticket to Hamilton, which I’d seen in LA previously, but he’d never seen and our tickets were a fraction of the price of the Broadway production or even what I’d paid in LA. Dear Evan Hansen was also playing and both shows had their online lottery, so if you want to save some money, but still see a show, make sure you download the Hamilton app and enter the lottery to win!

Day Two


Coffee and Churros at Xoco

For a sweet treat to start the second of your 3 days in Chicago, Rick Bayless’ Xoco (pronounced SHO-ko) is to die for. Freshly cooked churros with chocolate dipping sauce are a pretty decadent way to kick off the morning, but if you’re on holiday, who cares, right? The restaurant also serves up excellent Mexican street food including zingy empanadas and beautifully cooked tortas. The coffee here isn’t as great, with it being your stock standard American pot coffee, but today I’d recommend branching out (hell, you’re already having doughnuts for breakfast!) and try a chocolate cappucino! 


Take in the view at Signature Lounge

A beautiful view of Lakeshore, all the way up to the Gold Coast and beyond can be spotted from the Signature Lounge on the 95th floor of 875 North Michigan Avenue (the former John Hancock Center). The observation deck of the tower, 360 Chicago, is the floor below and thrill seekers might be keen to pay the extra cash in order to experience the Tilt, but if you’re looking for a more relaxing drink whilst you take in the view, then skip the Observation Deck and head up to the 95th floor to grab a beverage. In winter, the frozen lake Michigan looks spectacular from up high and to see it all with a local beer in hand is a brilliant way to escape the cold. 


Ohio Street Beach

In the winter, this might seem a strange thing to suggest, but a walk down to the shore of Ohio Street Beach is pretty magical. When I visited in early March, Lake Michigan was frozen over in shades of blue and white. For this Aussie girl, who doesn’t live anywhere near this cold, the spectacular sight of one of the great lakes solidified is worth braving the perishing Chicago wind to walk along the shore. 

Navy Pier

As the sun starts to wane, a walk along Navy Pier is a lovely way to see out the last of the day’s light. There’s a ferris wheel, food shops and in winter the pier is often mostly deserted. A lone wanderer here or there aside, winter at Navy Pier seems to be the perfect place to watch the sky turn colour against the chrome of the Chicago skyscrapers as if you’re the only person on earth. Either side of the pier is frozen water, broken up in parts by large boats moored against the boardwalk. The air gets chillier as the sun goes down, but nestled in my Chicago-bought down jacket, I’m warm and in no rush to leave.


Italian at Il Porcellino

I can’t think of a better dinner for the Chicago winter than a great, hearty Italian meal and for an Italian meal I’m not sure you can go past any restaurant better than Il Porcellino in River North. We waited for a table at the bar where two friendly bartenders started up a conversation over our Australian accents. With wine in hand, we were ushered to our table in the cosiness of the candlelit restaurant.

Hand made gnocchi in red sauce with a hefty taste of garlic and parmesan, accompanied by arancini and a bottle of a heavy Italian red wine is definitely my winter go-to and Il Porcellino did not disappoint. Even better, the bartenders sent us over a free apertivo after dinner. Beautiful food and even better service makes this restaurant a favourite for Chicago Italian. If you go out to dinner once during your 3 days in Chicago, let it be here. 

Day Three


Coffee at Goddess & The Baker

We definitely saved the best until last when it comes to coffee in Chicago. Goddess and the Baker is a colourful, caffeine haven full of beautiful edible goodies. The coffee here is wonderful, but the really special part is looking in the cakes and cookies windows to see what magical creations have been baked that morning. 

Wrigley Field

If you’re a sports fan then the iconic Wrigley Field will be a Chicago attraction you’ll be itching to see. Home of the beloved Chicago Cubs, the Wrigley Field area is quiet in Winter as baseball is out of season, but even just to walk around this stalwart of US Baseball is a great way to spend the mid-morning. Its hard to believe that this stadium has been around since 1914, making it the second oldest field in the major league behind Fenway Park. If you’re there in the off-season as I was, then I recommend a wander around the perimeter and a stop in at the Cubby Bar nearby for a drink. 


Al’s Italian Beef

It may be a chain, but everyone in Chicago we asked about the best Italian Beef roll told us to go without delay to Al’s Italian Beef. The concept is simple: a roast beef roll with optional green peppers and provolone dipped in gravy and it is oh so tasty. They have lots of things on the menu, but don’t get overwhelmed – the Italian Beef is what people keep coming back for and for good reason. The beef is tender and juicy, the peppers melt in your mouth and the provolone gives it that little zing. It may not look pretty, but it is delicious.


The Rookery

For architecture, Chicago is THE city in the US to visit. For my money, the best display of architecture in the city is the beautiful Rookery building in The Loop. It’s possible to enter the Frank Lloyd Wright remodelled atrium free of charge, though it is also possible to take walking tours through the Frank Lloyd Wright Trust during the week. The light filled atrium literally sparkles on entry and the hanging lanterns and sprawling staircases feel majestic. It almost feels like a palace in the heart of Chicago. 

Drinks at The Berghoff

When I found out that the establishment that received the first ever Chicago liquor license after prohibition was still running, I knew I had to go and have a drink there. The Berghoff, located in The Loop area is also a German restaurant, which was in existence before Prohibition and actually dates all the way back to 1898. The awesome thing about The Berghoff is that it is still family owned and run, so all of that amazing history is preserved. 


Eat a Chicago Style Hotdog at Portillo’s 

Another Chicago institution for dinner, this time at the incredible Portillo’s where hot dogs are taken to the next level. The Chicago hotdog is a beef sausage with onion, pickles and mustard, but no ketchup. Locals were very specific in telling me that no ketchup goes on a Chicago-style hotdog. If the pickle-heavy Chicago version doesn’t appeal, then Portillo’s has you covered with a regular hotdog or a chilli dog. In this funky, kitschy setting you’ll want to go back for seconds!


After Dinner

Blue Chicago

A quintessential Chicago night out involves good food, good wine and music. The city is teeming with jazz and blues bars with soulful musicians sharing their gifts with patrons for tips. Blue Chicago is the perfect winter blues hideaway. For a cash in hand entry fee you can relax and enjoy drinks whilst Chicago’s finest serenade you. The bar gets busy, so if you want a seat get there early, otherwise be prepared to stand shoulder to shoulder with locals and tourists alike who are all hear for the music. 

In summing up, there’s obviously so much of this wonderful city to discover and three days in Chicago barely scratches the surface of all the goods it has to offer. As soon as I set foot in the city I knew I was going to love it and it’s very quickly risen to being one of my favourite cities in the US. Hopefully you love it as much as I did!

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