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Cheap Flights to Chicago (CHI)

Flexible flights to Chicago
We've checked 1000s of popular dates for the best deals
Weekend Break Flights in Chicago
Go for a Weekend!
Departing
Nights
Prices from
September 3 £386.07
September 4 £371.07
October 3 £377.60
October 4 £362.07
November 3 £381.80
November 4 £368.27
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Short Break Flights in Chicago
Grab a Short Break!
Departing
Nights
Prices from
September 5 £368.67
September 4 £371.07
October 5 £362.07
October 4 £362.07
November 4 £368.27
November 5 £377.07
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Flights For 7nts in Chicago
Grab a Week Away!
Departing
Day
Prices from
September Mon £362.07
September Sat £417.20
October Mon £362.07
October Sat £393.67
November Mon £366.80
November Sat £396.80
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Travel Tips for Chicago


See all TravelTips for Chicago
 Chicago Blues Festival

posted by hcypret

If you can possibly coincide your visit to Boston with this annual festival, you should definitely check it out. In scale it eclipses all the English festivals and acts that perform are world class.

 City Segway Tours Chicago

posted by DVC_Chris

There are many ways to see the Windy City, the best way I have found to see Chicago is the City Segway Tours. We traveled on the public streets to see the city’s top tourist attractions, and learn about them for our guide, plus learning how to use a Segway is a great experience, and loads of ... more

 The Whitehall Hotel

posted by kumardeal

The whitehall Hotel offers a European sense of grace and grandeur including 222 magnificent guest rooms eight elegantly adorned suites individually controlled Air Conditioning/Heating Each room have satellite TV with a pay-TV, the hotel has 2 swimming pools with garden and solarium near the bar an ... more

 The Parthenon

posted by triplecrown

This is an authentic greek restaurant with great food and atmosphere. They had a varied menu and excellent service. We loved the location and would try the hotel next time we are in town, as it is within walking distance to the main attractions.

 Giordano's

posted by shenkcv

The ultimate pizzeria. Second best pizza i have ever had (Scotland being best). Not coming here while staying in Chicago is the equivalent of not visiting the Eiffel Tower in Paris. A must see, affordable delicious dining experience. Family dining is fairly cheap even though the price of visitin ... more

dealchecker's guide to Chicago


'The Windy City', as Chicago is known, sits on the shores of Lake Michigan in Illinois. It is one of America's busiest cities, a hub for commerce, and a dazzling playground for its visitors.

How to get there
Cheap flights to Chicago take about 8 hours from the UK with plenty of direct Chicago flights heading straight to O'Hare International airport, one of the States' busiest hubs. Scheduled services from British Airways, Virgin Atlantic and the US carriers such as American Airlines and United all operate from London, this is where you'll find the majority of direct flights. Chicago flights are also served with a range of indirect services operating from regional airports such as from Manchester, Glasgow, Birmingham and Belfast.

When to go
Chicago's nickname may or may not be due to the fact that it suffers some icy cold blasts off Lake Michigan during the winter months but whatever the case it's certainly not the best city to visit between December and March. Like many cities in the USA's northern states it does suffer a pretty harsh winter and in contrast a very hot summer with temperatures in July and August often over 30 degrees. The best time for holidays in Chicago depends very much on whether or not cheap flights to Chicago are your major driver. If they are then you're going to have to brave the cold. If you still want a relatively cheap Chicago flight but don't fancy having to take your entire winter wardrobe try April, May, June, September or October as a good time to visit Chicago. Flights are more expensive the closer you get to summer but then of course the weather gets progressively better too. Finally if you like it stinking hot and you don't care how much you pay for your flights, Chicago in July and August is within your grasp, it's also at the peak of festival season with loads to do and see but be warned it really can be very expensive to travel at this time. Make sure you compare Chicago flight deals with dealchecker to get the best possible price.

What to do
Chicago has a fantastic array of cultural attractions to match its breathtaking skyscraper filled city centre. It's also a great place to shop, eat out, watch sport and much more. There's certainly no shortage of reasons to bag yourself a cheap flight to Chicago. For a must see list of attractions try 'The Loop' just to the south of the Chicago River which is the city's traditional centre. You'll find Sears Tower here (the tallest building in the US with views over 4 states), the city's celebrated theatre district and the Art Institute of Chicago, one of the world's finest galleries covering almost five thousand years of art. On the other side of the river the 'Near North' is home to countless shops (try North Michigan Avenue to exhaust your credit cards) wonderful eateries and some fantastic buildings. It's also home to Navy Pier with a host of family friendly attractions. If you have more time why not arrange cheap Chicago car hire and visit Starved Rock State Park, which is an easy day trip from the city.

Whatever your reasons for visiting this great city, let dealchecker find you cheap flights to Chicago, then why not try our hotel search for cheap Chicago hotels too?

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