Holidays to Chicago

from as little as £524

3 nights in The Chicago Hotel Collection Magnificent Mile, Chicago, departing London Heathrow on 24 / Mar / 2025 with Austrian Airlines

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

Welcome to Chicago

Chicago holidays are perfect for those looking to venture to the United States and experience a city break like no other.

Nicknamed the Windy City, tourists can experience a captivating mix of history and culture. Dominated by stunning skyscrapers, the Chicago skyline is recognised across the world and contains some of the finest architecture you’ll ever see. From fascinating museums to lush green parks, and trendy restaurants to vibrant nightlife, there's plenty of activities to fill your time in Chicago!

Chicago

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 the 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 1,242 flights from the UK to or via Chicago every week, so you’ve got plenty of options. Icelandair often have the best flight deals, so keep an eye out for them in your holiday search results.

Key facts about Chicago

Holidays to other cities near Chicago

The above prices are guidelines only and are correct at the time of publishing. Subject to availability. Family prices are based on 2 adults and 2 children under 12 sharing a room. Other travel dates are available, supplements may apply. Please use the search box or call for details. For more information please read our Pricing Terms and Conditions.

Context Id: aed64b8a-2237-4406-968e-bdf30a591baf