How to spend 48 hours in Chicago

Ruben Quesada

Title photography by Rudy Balasko.

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December 2017

Steeped in history yet buzzing with a cool, contemporary vibe, Chicago teems with vibrant shops and galleries, show-stopping restaurants and slick bars, here’s how to make the most of 48 hours in the city. 

Day one

12.00 – Check In

Drop your bags off in your hotel – the four-star Hyatt Regency Chicago towers over the Chicago River and is on the doorstep of Millennium Park, Navy Pier and Lake Michigan. There’s no need to drive in the Windy City, most things are accessible via a quick train ride or on foot. The 29km Chicago Lakefront Trail not only provides dazzling skyline views, but also direct access to many of Chicago’s popular spots.

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With 4.6 billion years under one roof, you won’t be short of things to see - don’t miss Sue, the largest T rex ever found.

13.00 – Culture time

Spend the first part of your stay seeing stars at Chicago’s Adler Planetarium. Founded in 1930, the planetarium is the oldest in the United States and a must-visit for budding space explorers.

If sea life is more your thing, the Shedd Aquarium is just across the street, bringing you eye-to-eye with more than 32,000 aquatic creatures – you can even go behind the scenes on a shark-feeding tour.

Next door to the aquarium you’ll find The Field Museum, which was founded to house the biological and anthropological collections assembled for the World’s Columbian Exposition of 1893. With 4.6 billion years under one roof, you won’t be short of things to see – and don’t miss Sue, the largest T rex ever found.

  • Sleep easy in the comfortable surrounds of the four-star Hyatt Regency Chicago.

    Location location location 

    Head to the plush Big Bar for an evening aperitif. Open from 17.00 each day, take in the views from its panoramic windows. 

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  • Take a snap with the Chicago’s famous Buckingham Memorial Fountain © Getty.

    Make a splash 

    The fountain operates daily from early May to mid October. There’s a 20-minute water display every hour with water shooting 45 metres in the air. At dusk, the spectacle is accompanied by lights and music. 

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  • Sue the T-Rex is one of Chicago’s most famous residents © Chicago Tourist Board.

    Animal magic 

    Sue is the largest, best-preserved and most complete Tyrannosaurus rex ever found. She’s a whopping 12 metres from snout to tail and has 58 scary-looking teeth.  

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17:00 - All that jazz

Stroll through leafy Grant Park, pausing to photograph Chicago landmark Buckingham Fountain, before taking a quick train or cab ride north. Head to The Waterfront Café. Located in Berger Park, locals flock here to bag a table on the outdoor patio, which is partially covered by tropical trees and floral arrangements. Order a drink and a snack and enjoy the toe-tapping live jazz.

19.00 – Steak your claim

If only the best steakhouse will do, then Gibsons Bar & Steakhouse is for you. A Chicago institution since it opened in 1989, one juicy bite of its USDA Gibsons Prime Angus beef and you’ll understand why. Steaks aside, they do excellent burgers, seafood and desserts.

21.00 – Drink in the view

Head to the skies for a digestif at the Signature Lounge, located on the 96th floor of the John Hancock Tower. Floor-to-ceiling glass windows allow you to drink speciality cocktails with 360-degree views. If you only try one? It has to the ‘96 Reasons Why’ with vodka, apricot liqueur and Prosecco. 

  • Stop for dinner at the well-known Gibsons Bar & Steakhouse.

    Steak out 

    Cityfolk and visitors flock to classic American steakhouse Gibsons for its well-seasoned, full-flavoured, juicy steaks; expect huge portions (particularly the desserts) and sunny service. 

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Day two

09.30 – Munch on brunch

Start the day off at The Bongo Room, the place in town for breakfast and brunch. The breakfast burrito and croissant sandwich are classics – but you’ll be tempted by the seasonally changing pancakes and French toast creations, too.

11.30 – Hit the beach

Catch the Red Line train to Bryn Mawr to unwind at one of Chicago’s most popular beaches, Kathy Osterman Beach (aka Hollywood Beach) in the neighbourhood of Edgewater. Hungry beachgoers head to Nacho Mama’s Beach Bar, which serves an array of nacho and taco creations and frozen margaritas.

15.00 – Animal magic

Make your way back down the coast and stop into Lincoln Park for its superlative zoo. From aardvarks to yellow-spotted Amazon river turtles, you’ll discover a world of wildlife amongst the city’s skyscrapers - and the best bit? It’s free admission. 

  • Stroll along the impressive 28-kilometre Chicago Lakefront Trail for epic views of Lake Michigan © Getty.

17.00 – Follow the yellow brick road

A mere stroll away is Oz Park, named in honour of long-time Chicago resident L.Frank Baum, the author of The Wonderful Wizard of Oz. Here you’ll find statues of the Tin Man, Scarecrow, Cowardly Lion, and Dorothy and Toto, as well as the Emerald Garden and Dorothy’s Playlot.

19.00 – Reflect in style

Wrap up your day in the gilt and marble splendour of the lobby at the historic Palmer House. Order a drink, sink back in one of the comfy armchairs before heading for dinner at the in-house Lockwood Restaurant & Bar.

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