72 hours in Chicago: where to eat, stay and play

72 hours in Chicago: where to eat, stay and play

With stunning architecture, delicious food and plenty of sport on offer in Chicago, there is much to delight visitors in America’s third-largest city.

Due to a tragic fire in 1871, which destroyed about 8.5 square kilometres of the city, Chicago had to rise from the ashes. The result: a wonderfully laid out city, with tall towers set next to a wide river, for people to easily navigate and enjoy.

Dining experiences will be high on your agenda when visiting the ‘Windy City’ – Chicago-style hot dogs, deep-dish pizza pies and Italian beef sandwiches are all synonymous with the city.

This 72-hour itinerary in Chicago gives you the chance to sample the culture, indulge in the food and enjoy the entertainment, which continues to attract visitors from all over the world.

Day 1

9am – Uber to hotel

Arriving into Chicago O’Hare airport, the best way to transit to your hotel will be with an Uber.

I was fortunate to get a friendly Uber driver, Michael, on my recent visit, who also happened to work at the Art Institute of Chicago, a famous art and culture museum in the city.

He suggested several great eateries to try and the styles of food to add to my list. Top tip: Always chat to the locals – they’ll give honest advice on the best spots to visit.

I dropped off my luggage at the Freehand Hotel and headed out for a bite nearby.

Uno Pizzeria & Grill Chicago
Uno Pizzeria & Grill Chicago

11am – Lunch at Uno Pizzeria & Grill

For a traditional Chicago-style deep dish pizza pie, there’s no other like the 75-year-old establishment Uno Pizzeria & Grill on East Ohio.

The pizza pie combines stretchy cheese, perfectly spiced sausage and a rich tomato sauce all layered into a crumbly, buttery crust. Paired with a local beer, this makes the perfect first meal in Chicago.

A lesson I learned from my first experience of this style of pizza back in 2009 is to trust the waiters’ recommendations. Also, always order a small – they may look tiny, but these babies will fill you up.

Freehand Hotel Chicago
Freehand Hotel room Chicago

1pm – Check in at the Freehand Hotel and nap

It’s time to head back to the hotel because after that meal, a nap is needed.

Fortunately, I was able to check in early at the Freehand Hotel – boutique and centrally-located accommodation housed in a classic 1927 building.

This charming hotel has a coffee shop, cafe and bar located on the ground floor.

The history of the building is maintained in its structure and design, while the vibrant and uplifting decor gives it a youthful makeover.

Large beds and sweet little touches make this a cosy stay, and the perfect place to catch up on some rest after a long journey.

NHL Ice Hockey Chicago

7pm – NHL (ice hockey)

Whether you’re a sports fan or not, the National Hockey League (NHL) is an experience like no other.

Held in the United Center, I joined thousands of fans to support the local Chicago Blackhawks play the LA Kings.

Pumping music, colourful lights and cheering fans add to the electric atmosphere in the stadium as you watch the two teams skilfully navigate the ice.

Beers and hot dogs seemed to be the cuisine of choice and made me feel like a local.

If you’re lucky, you may even get to experience the excitement of overtime and a penalty shoot-out.

Chicago city and river

Day 2

9am – Stroll through the city

Start your day with a walk to admire the incredible architecture that Chicago is famous for.

From the central hotel district, enjoy a 2km walk past the river to view the epic skyscrapers such as The Willis Tower and the John Hancock Building. If you have a clear day, be sure to head to the top for an incredible view.

If visiting in the winter, as I did, the walk may be a bit intense in the cold. If so, opt for an Uber as an affordable and comfortable way to travel short distances.

Art Institute of Chicago
Art Institute of Chicago
American Gothic at Art Institute of Chicago
Art Institute of Chicago Museum Cafe

10am – Art Institute of Chicago

Voted as the Traveller’s Choice of top 25 museums in the world on TripAdvisor three years in a row, the Art Institute of Chicago allows guests to experience a range of art, from ancient treasures to modern icons.

The highlight for me was seeing American Gothic (pictured, above). The painting is instantly recognisable as it’s one of the most frequently parodied pieces of art in pop culture.

At my Uber driver’s recommendation, I enjoyed lunch at the Museum Cafe and tried the famous Chicago-style hot dog.

Loaded with chopped onions, green pickle relish, pickled peppers, dill pickle and yellow mustard, this is a flavour explosion. Pair it with your choice of a side (the German potato salad was excellent) and this meal will keep any busy traveller going for a day of sightseeing.

Millennium Park The Bean
Millennium Park giant faces

2pm – Millennium Park

After the museum, walk across the road and through the beautifully manicured grounds of Millennium Park. Here you can pose for a photo with the iconic art installation The Bean.

The park also hosts other installations, such as the giant faces on LED screens. They’re as creepy as they are fascinating.

Palmer House Chicago
Drinks at Palmer House Chicago

4pm – Palmer House for afternoon cocktails

Experience the old-world charm of Chicago when you step back in time at the Palmer House Hilton.

Sitting at the bar in the exquisite decor of this hotel, built in 1923, I was transported to an era of class and sophistication.

Ask the bartender for a recommendation, otherwise a champagne cocktail was my drink of choice as I sipped and admired the decadent surroundings.

Chicago Bulls NBA game
Rock Bottom Brewery
Rock Bottom Brewery buffalo wings

7pm – NBA game

Even though I’m not a sports fanatic, experiencing an NBA (National Basketball Association) game, and a team as iconic as the Chicago Bulls, is a must.

Cheerleaders, chants, prizes and big-screen action such as the Kiss Cam will entertain you throughout the night.

Oh and, of course, there’s the talented players showing off their impressive skills on the court too.

10pm – Late night wings and beers at Rock Bottom Brewery

The day isn’t done and a late-night session at a bar is a must in this bustling city.

With a craving for real American chicken wings, Rock Bottom Brewery delivered the goods.

As an actual brewery, craft beers are made on site, and I was delighted by the local offerings paired with delicious buffalo wings.

This is the perfect end to a big day of sightseeing in Chicago.

Cafe Integral Chicago

Day 3

9am – Brunch and coffee at the hotel

The beauty of staying at the Freehand Hotel, which comes complete with a cafe and restaurant, is that it makes breakfast decisions easy.

As Australians, we’re picky about our coffee. But the hipster vibe of Cafe Integral lived up to expectations and I enjoyed the perfect morning brew.

They even offered avocado on toast – I felt right at home.

Shedd Aquarium, Chicago
Shedd Aquarium, Chicago

10am – Shedd Aquarium

With a marine biologist as my travel companion, Shedd Aquarium was a natural choice for a day out, though I didn’t expect the building to be so delightfully on theme or so beautifully in sync with its contents.

The features and facades merged with the building; items were not just stuck on to make the building aesthetically pleasing, they became a part of the building.

With a trident atop the outer dome, lobsters for door handles, dolphins in the alcoves and shells for lamps, this building was always intended to be an aquarium.

The highlight was the belugas. Rarely seen in aquariums, these unusual looking whales swam majestically below the surface and chattered playfully above, making them a joy to watch.

Leave some time to stroll around the Museum Campus, home to five of Chicago’s well-known attractions including the Field Museum of Natural History, the Adler Planetarium, the Chicago Bear’s NFL team home ground Soldier Field, the Lakeside Center of McCormick Place and, of course, the Shedd Aquarium.

Portillo's Chicago

2pm – Lunch at Portillo’s

The only way to finish a visit to Chicago is to eat at local institution, Portillo’s. It is a must-visit for some incredible local eats and traditional service.

This enormous restaurant is home to some of the city’s incredible history in the memorabilia collected over the years. It’s like eating in a museum.

I ordered an Italian beef sandwich – a soft roll stuffed with tender, slow-cooked beef and dipped in meat juice. Yes, and get this: you get to choose how far it’s dipped in the juice.

With a great atmosphere and delicious food, Portillo’s is a true Chicago experience.

Getting to Chicago

Getting to Chicago

Traveling to Chicago from Australia has become easier with Air New Zealand introducing a non-stop flight from New Zealand.

Flights from Sydney now take a more direct route stopping only in Auckland before heading straight to Chicago, avoiding a transit in Los Angeles.

Chicago is also a major domestic hub for connecting to other North American destinations, making it easy to plan your onward journey.

Emma Lovell, She Defined author

Emma Lovell

Emma Lovell is a writer with a passion for travel, social media and adventure.

When she’s not travelling, she’s documenting her stories and planning the itinerary for her next journey.

Based on the Gold Coast, she loves getting to the beach and soaking up the best her local area has to offer.