Your Guide to Chicago

City Breaks | | 5 minutes
Aerial view of Chicago | Your Guide to Chicago

Chi-town. The Windy City. Chicago has always been a popular city with the Irish. It’s a big city, but not as overwhelming as cities like New York and equally spectacular to behold. Known for its amazing architecture, its deep-dish pizza, its mobster past and its sports teams, Chicago is a vibrant city with endless things to do, see and eat.

What to Do in Chicago

Willis Tower

Completed in 1973, the Willis Tower is the 12th tallest building in the world. Its Skydeck, at 1,353 feet high, is the highest observation deck in the United State. Step onto The Ledge, a glass observation box, to feel like you’re floating above Chicago’s streets. On a clear day, you can see for 50miles taking in the states of Illinois, Indiana, Wisconsin and Michigan.

Architectural River Tour

Chicago is famous for its architecture and its skyscrapers. From art-deco to modern glassy mammoths, on the Architecture River Tour, you’ll learn about 50 of Chicago’s most iconic buildings. Run by the Chicago Architecture Foundation, this is expert-led tour is a great way to learn about the city’s history.

Visit the World’s Largest Rooftop Bar

On a sunny day, who doesn’t love a nice rooftop bar? Located on Chicago’s famous Navy Pier, Offshore is on the third floor of the Festival Hall at the end of the pier. With unmatched views of Chicago’s skyline and Lake Michigan, it’s the perfect place to watch the sunset, sitting by a fire pit on the outdoor terrace with a cocktail in hand.

Second City

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In 1959, Second City opened its doors. Co-founded by Paul Sills, considered to be the founding father of improvisational theatre, Second City has become an important part of comedy in North America. It launched the careers John Candy, Steve Carrell, Stephen Colbert, Tina Fey, Bill Murray, Mike Myers and many more. During your visit Chicago, an evening at Second City, laughing with future comedic superstars is an evening well spent!

The Green Mill

The Green Mill has been a big part of Chicago’s jazz scene since before Prohibition. In fact, it was a popular hang out for Al Capone and other gangsters from the Prohibition-era! You’ll feel like you’ve stepped back in time here from the smooth jazz to the classic cocktails and (now) antique décor.

What to See in Chicago

Millennium Park

Millennium Park is a gorgeous spot to embrace some nature on your visit to Chicago. Cloud Gate or ‘The Bean’ sculpture is the #1 spot for selfies in Chicago. For a tranquil break, visit Lurie Garden. If you want some lunch, head to Plaza at Park Grill where you can enjoy some food, views of the city and often live music. Enjoy some outdoor art at the Boeing Galleries where outdoor sculptural exhibitions take place throughout the year.

Wrigley Field

The Cubs at Wrigley Field got international attention in 2016 when they ended their 108-year losing streak by winning the World Series. Their 108-year losing streak was the longest in all of the major North American sports. To learn about this iconic ballpark, you can either attend one of the Cubs games or get a tour. Tickets for a game go for as little as $49 or the tour for $30.

The Riverwalk

Stretching for 2km along the Chicago River, the Riverwalk is like another park within the heart of the city. Divided into 6 distinct districts, each part of the Riverwalk has something different to offer you (besides its amazing views of the cityscape).

  • The Marina (State to Dearborn): Here you’ll find lots of seating, plenty of restaurants and views of the iconic “corn cob” buildings.
  • The Cove (Dearborn to Clark): Is the place to go if you want to rent a kayak and explore the city from Chicago River.
  • The River Theater (Clark to LaSalle): A leafy, tree-covered escape in the city, the River Theater is ideal for a sit-down and to chill out.
  • The Water Plaza (LaSalle to Wells): Here you’ll find a fabulous fountain, ideal for adults to relax around or kids to splash in.
  • The Jetty (Wells to Franklin): This is a series of floating wetland gardens, the perfect place to learn about the ecology of the river or do some fishing and bird watching.
  • The Confluence/Boardwalk (Franklin to Lake): Is where you can see the 3 branches of the Chicago River. With plenty of seating and a lawn, it’s a lovely spot to watch the river flow by.

Magnificent Mile

The Magnificent Mile comprises of 13 blocks, 460 shops, 275 restaurants and 60 hotels. From entertainment to dining or retail therapy, it has something for all your needs. It’s also some to some of Chicago’s most famous buildings like the Chicago Water Tower, the neo-Gothic Tribune Tower, the terracotta Wrigley Building skyscraper and the 100-story John Hancock Center.

Where to Stay in Chicago

The 3* Tremont Hotel

Located on the Magnificent Mile, this is the perfect base to explore all Chicago has to offer. From finding the best Chicago deep-dish pizza to exploring the Magnificent Mile, the location couldn’t be better. Rooms are spacious, stylish and comfortable – what more do you need!

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