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Cheap Holidays to Chicago

Book your cheap holiday to Chicago with Flight Centre.

When you book your Chicago holiday with Flight Centre our expert travel consultants can advise you on all the best available holiday packages to suit your needs whether it is for family fun, couples, night life or anything else we will ensure you pay the best possible price.

Cheapest Holidays to Chicago

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Holidays to Chicago

Cutting-edge architecture, legendary blues, and scrumptious dining? Check. Lavish shopping, world-class museums, and lake views? Check. Glorious parks, major-league baseball, and side-splitting improv? Check. Deep-dish pizza, piled-high hot dogs, and Italian beef sandwiches? Check. Chicago's got it all—now all you need to do is book a holiday!

The hub of the midwest and the third largest city in the USA, Chicago might not be as well known as it’s east and west coast city counterparts but those who do take a detour to the vibrant city are never disappointed. Chicago enjoys a picturesque location on Lake Michigan, made even more pretty with the city’s notable parks and incredible architecture - its downtown collection deemed to be some of the finest in the world. With such a celebrated landscape the city has also followed in the footsteps of Los Angeles and New York, Chicago also has a fine grasp on the TV and movie industry with Chicago-centric productions including The Blues Brothers and Ferris Bueller’s Day Off. Such is the charm of Chicago. There are icons to be found and big city moments to be had, but with more mystery than that of New York and LA there’s room to do some exploring of your own.

Fast Facts

Language: English

Currency: US Dollar

Population: 2.8 million

Main International Airport: O'Hare International Airport


As in New York and other large cities, visitors to Chicago are spoiled for choice for sights to see, things to do and places to indulge. Music lovers will love the blues scene, which still thrives in clubs from the South Side to the North Side. If that is not your scene the city also offers classical, folk, rock, alt-country, or whatever genre captures your fancy. The summer's free concert series in Grant Park and Millennium Park consistently draw top-tier performers.

Chicago is also place renowned for its architecture. Frank Lloyd Wright fans will be delighted to see his earliest buildings in Chicago, where he began his professional career. Three out of America's five tallest buildings are in Chicago including the Sears Tower (1st) and the Trump Tower (2nd). The Aon Center Architectural tours cover the landmarks on foot and by popular river boat tours. Another fantastic view can also be found on one of the downtown bridges over the Chicago River. And if music and buildings aren’t your thing, how about a feast of top rate sporting events spanning football, baseball, basketball and ice hockey? Attending one of these games is a great way to get a sense for the Chicago spirit and way of life.

Where to stay

Like any big city in the USA, accommodation in Chicago caters for all types of travellers and budgets. Hotel rates fluctuate wildly according to season, festivals and events and even day of the week – so check for bargains because room rates can drop $50 to $100 overnight—and rise again the next day. Also consider your accommodation based on an area of interest, such as the Magnificent Mile area and the rest of the Near North side.

When to go

Just because they call it the Windy City doesn’t mean you can count on it. When it comes to weather, Chicago is a mixed bag. Cold and windy, warm and humid - whatever the time of year and whatever the weather, there’s always a great reason to visit though. Some of the most consistently good weather occurs in June, September, October, April and May. Be aware, however, that thunderstorms can occur suddenly. July and August are okay but can experience heat wave conditions if the rest of the country succumbs too. Snow is limited to a handful of heavy storms per season. Chicago is a city that's well-accustomed to the winter season, so city services and public transportation are highly unlikely to ever shut down.

Captain's Travel Tips

Like NewYork, Chicago is a big city that is easy to navigate. In general, "avenues" run north-south while "streets" run east-west complete with a logical numbering system. The best way to see Chicago is by public transport, either train or bus or a combination, which is cheap, mostly efficient and quite safe. Just note the name and colour of your home and your destination and the city is yours for the day.

How to book your Holidays to Chicago

Why choose Flight Centre?

At Flight Centre we’re well known as the leading retailer of airfares and worldwide flights and we’re old hands at giving you no-nonsense advice on getting from A to B. With over 30 years of experience in travel, our business has grown into many areas of expertise and simply there’s much more to Flight Centre than flights alone. Round the World Experts are our tailor made specialists, First and Business are experts in premium airfares and hotels and Flight Centre Business Travel (FCBT) offers contract free, low cost business travel service.

We have over 800 travel experts in Flight Centre stores stretching from Scotland to Brighton. They can tailor any flights to your trip, tastes and budget. Tell us how much time you have and your reason for travelling and we’ll do all the legwork. No more poring over travel comparison and review sites for hours trying to second guess small print or fare restrictions, our experts will find all the options available.

Find us in over 85 locations across the UK, open 7 days a week, from Monday to Friday 7am to 11pm or at weekends from 8am to 10pm. Call free on 0800 587 0058 or from your mobile on 0333 333 2211.

Whether you’re after a stopover on a business trip, a city break, beach holiday, adventure safari or simply a great price on a flight, our competitive offers make sure you get the best deal available. Our Fly for Free promise means if we can’t find you a cheaper airfare in the same cabin, you’ll fly for free. We promise to beat any quote from another UK high street travel agent, online travel agent or call centre, for scheduled flights departing the UK.