The ultimate Route 66 flights: London → Chicago, LA → London 🚗 🇺🇸 ✈️

Always fancied driving Route 66? This flight combo makes it surprisingly easy to plan your own classic American road trip, just in time for the highway's 100th anniversary!

Right now you can fly London Heathrow → Chicago, then return Los Angeles → London Gatwick for just £518, giving you 3+ weeks to explore the USA at your own pace.

Even better, these flights are all in September, one of the best months for a road trip with warm weather, clear skies, and fewer crowds.

💡 Act fast: the same flights jump to roughly double the price just one week later. If you’ve been dreaming of a Route 66 adventure, this could be one of the most affordable windows to make it happen.

💥 This is a DIY itinerary, meaning you'll book each leg separately using Skyscanner, giving you maximum flexibility to design your own route.

Details

Details:

✈️ The Route: London ➝ Chicago ➝ Route 66 ➝ Los Angeles ➝ London

Example booking.

London Heathrow ➝ Chicago (one way) = £369:

Los Angeles ➝ London Gatwick (one way) = £149

Alternative flights/dates:

London ➝ Chicago one way

Los Angeles ➝ London one way

Additional Information

We might be pirates, but we’re an honest bunch. We check all our deals when we review them to make sure everything is available. However, with deals this hot, things change quickly—flight prices fluctuate, hotel rooms sell out, currencies yo-yo. But mainly, demand for the best deals means the lowest prices don’t last long. If you’ve missed out this time, don’t worry, we’re working on more great offers.

Interested in offsetting your carbon emissions for this flight? Read our guide to help you make an informed decision.

Travelling solo? Check out our single-travel deals here.