Deposits from €25
Deposits From €25pp on USA Holidays
Deposits From €25pp on USA Holidays
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Spread the Cost With Monthly Instalments
Explore exclusive Chicago package holidays from Dublin, Cork, and Shannon. Secure your Chicago Holiday from just €25 today, and spread the cost with monthly instalments. Find great deals on flights and accommodation – book online today!
from Dublin - 17 Jan 2027 4 Nights for 2 adults
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from Dublin - 23 Nov 2026 4 Nights for 2 adults
Book NowDon’t miss the opportunity to visit the city that remains one of the true jazz capitals of the USA, with cheap holidays from Dublin to the heart of Chicago. The third largest city in the United States, Chicago is located on the Southwestern shore of Lake Michigan and makes for an amazing destination for any kind of holiday. Fall in love with the windy city with its dozens of cultural institutions, historical sites and museums on your spectacular Chicago holiday!
There are regular flights from Dublin to Chicago with Aer Lingus, with an estimated flight time of 8 hours and 40 minutes.
To learn more about things to do in Chicago, the best time to go and local info see here.
Chicago is renowned for its iconic house music scene, with the hypnotic electronic records attracting hoards of party goers looking for a good time. With great dance parties, bars and clubs waiting for you, you won’t be short of having a good time in Chicago.
Chicago is famed for its deep dish pizza, but the cuisine stretches past just pizza! Try some of the city's fresh seafood during your visit. There's also plenty of places to try new cuisines like Korean food, but if you're craving some home comforts there's lots of gastropubs too.
Chicago has something to do for the whole family. Enjoy a day trip to Brookfield Zoo where you can see the over 2,000 animals who live there, or visit Millennium Park which hosts a range of different activities throughout the year.
When shopping in Chicago be sure to check out the Magnificent Mile, which boasts more than 460 retailers and is home to many popular brands, major department stores, designer labels and 3 shopping centres. This is the perfect place to pick up some bargains on your Chicago holiday.
A trip to Chicago can be taken year-round, but between April to May and September to October tend to be particularly popular as this is when temperatures are at their most enjoyable and there is an abundance of festivals and events taking place.
The US Dollar is used in Chicago.
Dublin is 6 hours ahead of Chicago.
Chicago is very easy to get around, with public transport options including trams and trains, busses and taxis being readily available. Walking and biking are also enjoyable ways of seeing Chicago, while taking a water taxi can be a fun and memorable experience.
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