Booking flights from London to Chicago is less about logistics and more about dreams. The Windy City is the kind of place that fires the imagination. There are tales of gangsters and speakeasies in the city of Al Capone. There are soaring towers that really do scrape the sky. And there are basement blues to swallow your soul. Spending fewer pounds on the flight means more dollars for your stay. So let's talk logistics first, and dream later.
The best months for low prices are February and March. But beware: winter is at its fiercest during these months and you'll need more than a bobble hat to keep warm. September is low cost and far warmer, while July and August are peaks in both price and summer heat. Thursdays are the lowest-cost days for London Chicago flights, and if you choose an evening flight you'll save more than a few cents.
Both Heathrow and Gatwick have cheap options for your flight to the Windy City. Heathrow is well-served by the Heathrow Express train, with a single costing £18. Coaches from central London stops can be as little as £4. Gatwick, 30 miles south of the capital, has both the Gatwick Express and Thameslink trains running to it from London. Fares are £10 for the slower Thameslink and £20 for the faster Express.
Direct isn't always cheapest on this route, so it may be worth stopping over at a Midwest airport like Detroit or Minneapolis. Airlines offering such London Chicago flights include Virgin Atlantic and Delta Airlines. This will add an hour or two to your journey, making it last 10 to 12 hours. Direct flights from United Airlines, Lufthansa or British Airways can get you to O'Hare International in as little as 7 hours. Though, with Chicago 6 hours behind the UK, you'll hardly lose any of your day.
O'Hare International (ORD) is the airport of choice for planes coming from London to Chicago. It lies 17 miles northwest of the city, with good links back to the Loop. The CTA Blue Line train trundles into Chicago in less than an hour every 15 minutes. It runs 24/7 and costs $5. Allow a bit of extra time to get to the station if you're landing at Terminal 5. Taxis are thick on the ground and a good way to see the sights – but will set you back $40.
Chicago is a huge city, packed with surprise and spectacle, and more than a little soul. From the swaying pinnacle of Willis Tower, its highest point, you'll get the scale of it. Down along Lake Michigan's shore you can stroll through the breezy parks of Lakefront and admire the breath-taking Chicago skyline. The museums here, from the Art Institute of Chicago to the Museum of Science and Technology, are full of mind-blowing marvels. To the west, the marvels switch to retail, in what they call the Magnificent Mile. This is the place to flash the plastic and then swing those shopping bags. Or you could just curl up in basement bar, and let the blues sweep you away.
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