City Guides

72 hours in beautiful Chicago

A quick guide to exploring the Windy City's stunning architecture, hip neighbourhoods and trendy eateries.


Checking in

Stay in the heart of the action at the Hilton Chicago, one of the city’s largest and most iconic hotels. The lobby dazzles with stunning ceiling murals and grand columns. Its prime location on Michigan Avenue means it’s a short walk away from the main attractions (including the beach!) and accessible to all areas of the city via subway. Grant Park is across the street, home to Millennium Park, Buckingham Fountain, the Art Institute of Chicago and Museum Campus.

If you’re craving a more hip and low-key vibe, check out the six rooms on offer at Longman & Eagle, one of the city’s buzziest eating and drinking establishments. Located in Chicago’s hip Logan Square neighbourhood, the rooms feature televisions equipped with Apple TV, designer furniture and rotating works of art from up-and-coming artists. Some rooms even come with vintage cassette players and a selection of mix tapes. The best part? You’re just a few steps away from one of the best places to enjoy a craft cocktail or rare whiskey (there are over 300 on the menu!). Pair it with a dish by their Michelin Star-awarded executive chef, Jared Wentworth.

72 hours in beautiful ChicagoHilton Chicago ceiling mural. Photo, Dominique Lamberton

Dinner hour

If you want to see, be seen and enjoy hot cuisine, reserve a table at the Michelin-recommended Asian fusion restaurant Sunda. The menu is designed for sharing, so gather your group and feast on small fusion plates and specialty sushi. Order the addictive Crispy Brussels Sprouts, served with chilies and fried shallots, Oxtail Pot Stickers and the Spicy “Tail of Two Tunas” rolls. And be sure to save room for dessert – the “Ridiculous” is exactly that and you’ll definitely want to share this creation of vanilla ice cream surrounded in a layer of ginger carrot cake and smothered with caramel sauce. Bonus: They have dedicated gluten-free and vegan menus.

Northwest of downtown in Wicker Park, you’ll know before you even step into Big Star that you’ve arrived at a happening spot. Sip margaritas on the large patio or around the bustling 360-degree bar, and feast on tacos filled with beer-battered tilapia and crispy pork belly.

72 hours in beautiful ChicagoBig Star restaurant. Photo, Dominique Lamberton.

Explore the sights

A trip to Chicago isn’t complete without snapping a selfie in front of the iconic Cloud Gate sculpture, more commonly known as The Bean, in Millennium Park (located in Grant Park). There’s much to see and do in the 24.5-acre cultural playground, and the museum options alone are endless, with the Art Institute of Chicago, Adler Planetarium, Shedd Aquarium and Field Museum of Natural History all within walking distance of one another.

Chicago’s famous architecture is best taken in from the water, on one of the many boats that cruise the river. Book a spot on Chicago Line Cruises, whose guides are informative and entertaining on the 90-minute tour. Come with an empty memory card and be sure to get your fill of the complimentary fresh lemonade and cookies served below deck!



  72 hours in beautiful ChicagoChicago river. Photo, Dominique Lamberton.

Shop till you drop

Even if you’re not dining in Eatly, Mario Batalli’s complex that houses 23 eateries and a cooking school, a visit to its Market is a must. Shop the selection of fresh pasta and cheeses, visit the fishmonger and butcher, and peruse the pastries and chocolate. There are even beauty and housewares departments. Prepare to spend a few hours here.

Back in Wicker Park, stop into Eskell, a charming boutique where you’ll find a curated selection of jewellery and housewares (think potted succulents, Volupsa candles, coffee table books and vintage-looking birdcages), as well as the shop’s own line of clothing.

72 hours in beautiful ChicagoEskell. Photo, Dominique Lamberton.

Classic Chicago eats

The city of many nicknames (Chitown, the Windy City, Paris on the Prairie… the list goes on) also has many classic dishes that one simply must indulge in before leaving the area. For classic Chicago deep-dish pizza, head to Lou Malnati’s (there are 37 locations in the city) and order The Malnati Chicago Classic, featuring sausage, extra cheese and lots of tomato sauce all piled on a butter crust. Get your fork and knife ready – there are no handheld slices here.

For a delicious souvenir, get a tin of Garrett Popcorn in Garret Mix (commonly known as Chicago Mix) – kernels covered in savoury cheddar cheese are mixed with ones covered in sweet caramel. A deadly and addictive combo!

Lou Mainati deep dish pizza ChicagoLou Malnati's Chicago deep-dish pizza. Photo Dominique Lamberton.


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