Chicago City Breaks

Think windy walks along the magnificent Lake Michigan, days filled with awe-inspiring skyline views from towering landmarks, and nights immersed in vibrant live blues melodies. A city break to Chicago offers an unmatched blend of grand architecture, stunning natural vistas, rich history and cultural pursuits that impress families, friends, and couples alike. Be it lazy afternoons at world-class museums or evenings cheering on a legendary sports team, the Windy City caters to every budget, taste and adventure.

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Attractions

From the lofty heights of its celebrated skyscrapers to the bustling energy of its colourful neighbourhoods, Chicago holds a cornucopia of experiences waiting to be discovered. Here are our top recommendations that you simply cannot pass up!

Amble on the Navy Pier

Located on the city's lakefront, Navy Pier is a vibrant hub of attractions, dining, and entertainment. Don't miss the frequent live music events, the iconic ferris wheel, or the chance to taste some famous deep dish pizza in one of the numerous eateries.

Ascend Willis Tower's Skydeck

Assert your dominance over the Windy City by experiencing the Skydeck on the 103rd floor of the Willis Tower. This spectacular observatory lets you enjoy a panoramic outlook over Chicago, and for the daring, stepping out onto the transparent ledge is a must!

Stroll the Chicago Riverwalk

Discover the charm of the city by the waterside. The Chicago Riverwalk offers a stunning path that highlights the city's astounding architectural feats. Relax at one of the open-air cafés or delve into rich local history at the Chicago River Museum.

Discover Millennium Park

Synonymous with the city itself, Millennium Park hosts the famous Cloud Gate, locally known as 'The Bean'. Enjoy free concerts at the Jay Pritzker Pavilion, wander through the beautiful Lurie Garden, or skate at the McCormick Tribune Ice Rink during winter.

Step Back in Time at The Art Institute of Chicago

Home to thousands of works from all corners of the globe, The Art Institute of Chicago is an absolute haven for art enthusiasts. Explore the vibrant contemporary art section or revel in the classic masterpieces that have revolutionised art history.

City Essentials

Every season offers a different charm to Chicago with its unique allure. For pleasant weather and manageable crowds, springtime (April-May) and autumn (September-October) are ideal. These seasons are perfect to explore parks and take pleasure in open-air concerts or baseball games.

The summer season (June-August), although slightly crowded, is excellent for enjoying the glorious beaches, outdoor food festivals and music extravaganzas such as Lollapalooza. Winter in Chicago (November-March) can be bitter but offers sensational deals for those brave enough to stand the chill. Witness the city turn into a snowy wonderland and enjoy ice-skating at Millennium park or explore heated indoor attractions like the Field Museum.

Nightlife

Whether you fancy a jazzy club, an elegant theatre evening or a rich local brew, Chicago’s nightlife caters to every mood and taste. Explore the electrifying blues scene at Kingston Mines or visit The Second City for its famous improv and sketch comedy shows.

Head to Hubbard Street and West Loop for nightclubs that throb with energy until dawn. Looking for a relaxed drink? Try the local craft beer at bars like Hopleaf or Fountainhead.

Chicago's food scene also comes alive at night. Opt for Italian cuisine in Little Italy, mouth-watering BBQ in West Loop, or authentic Mexican fare in Pilsen.

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