Holidays in Chicago

Holidays from as little as £577

3 nights in The Pittsfield Hotel, Chicago, departing London Gatwick on 10 / Dec / 2019 with British Airways

Subject to availability, prices correct of the last 24 hours
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Welcome to Chicago

If you're looking for a cheap holiday to Chicago, you've come to the right place. We search and compare loads of deals every day, to help you find that best price. What are you waiting for? Find the best Chicago trip for your budget with Netflights.

Our holiday guide to Chicago

Price hacks, travel tips and more

Fancy a city break to Chicago? At Netflights, we compare hundreds of holidays to Chicago to help you get more bang for your buck. Whether you’re after a romantic getaway, a family holiday or a trip with your mates, we’ve got just the thing.

Chicago is a popular holiday spot in USA but prices vary throughout the year. If you want a cheap deal, try looking for holidays in January, when prices are at their lowest. September is the most popular time to visit Chicago so, if you want to go then, it’s best to book in advance.

If you’re flexible on travel dates, try searching for holidays to Chicago by month to find the cheapest deals. It’s also worth considering different flying days – flights will probably be cheaper on a Tuesday than a Friday, for example.

There are roughly 1,559 flights from the UK to or via Chicago every week, so you’ve got plenty of options. KLM often have the best flight deals, so keep an eye out for them in your holiday search results.

Flights to Chicago from the UK

from £332 pp
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from £433 pp
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from £454 pp
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from £389 pp
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from £620 pp
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from £399 pp
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Holidays to other cities near Chicago

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