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Holidays to Chicago

A vibrant city full of activities, a holiday to Chicago is ideal for shopaholics and sport lovers. With 26 sandy beaches and 46 km of lakefront, it offers the perfect combination of natural beauty and man-made wonders!

SHOPPING - Shopaholics will already know about the Magnificent Mile in Chicago, which crams three indoor malls and 50 flagship stores into just one mile along North Michigan Avenue! American Girl, a multistorey doll emporium, is one of the most-visited store attractions in town - don’t miss it if you’re travelling with kids.

ACTIVITIES - See all the top sights at your own pace by jumping on the hop on hop off bus. For an alternative view of the city take a river tour, or if you’re feeling more active, rent a bicycle and cycle along 42 km of uninterrupted lakefront. Standout buildings include the Wrigley Building, Willis Tower and Trump International Hotel & Tower.

DINING OUT - There are over 5,195 restaurants in Chicago! Take a culinary tour of Chicago’s diverse and delicious ethnic neighbourhood eateries, by heading to Fulton Market, Logan Square and River North. There is a great range of craft beer in bars around the city, or if you fancy something with a view choose one of the many skytop cocktail bars with sparkling views of the city, like Rebar or Roof.

SPORTS – You don’t have to be a diehard sports fan to enjoy a game in the Windy City! Chicago has a range of famous sports teams, and you can watch anything from baseball, football and basketball to hockey, soccer, and horse racing!

NEARBY – Just over 1 hour by car from Chicago, Michigan city is perfect for a day trip, with its opulent mansions, steam locomotives and Historical Societies which give you a glimpse into the past. Alternatively, Milwaukee is just 90 minutes by train!

BEACHES – You may be surprised to know that Chicago boasts 26 sandy beaches! You can dip your toes into the cool waters of Lake Michigan, relax on Montrose Beach, go wild at 31st Street Beach, or chill out at the peaceful and more relaxed 63rd Beach.

At Cassidy Travel, our expert travel team can help you make the most of your holiday to Chicago. We book thousands of holidays to America from Dublin, Cork, Knock and Shannon each year, and we can help you find the best USA holiday deals whether you’re looking for a group trip, a family holiday or travelling with that special someone. Check out some of our deals on Chicago holidays below, or get a quote above!


There are direct flights available from Dublin to Chicago. Want to make the most of your USA trip? Why not add a trip to Miami or LA with a Multi Centre Holiday?

Getting Around

O’Hare Airport is located 24 km from downtown Chicago, and it takes around 40 minutes on the Blue Line train service to get into the city. Trains run every 30 minutes, and there are a number of taxis and shuttle services available.

Deposits from €50pp!