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Flights to Chicago

Chicago city

Fly to Chicago from £569* and be blown away by all the windy city has to offer.

America’s third largest city, Chicago sits on the shores of Lake Michigan in the heart of the Midwest. The birthplace of the skyscraper, this city is a highlight for architecture enthusiasts. For the easy way to take in the dramatic skyline, jump on a Chicago river cruise.

Millennium Park offers loads of activities for families on holiday in Chicago, along with a spectacular collection of landscape design and art. Enjoy Chicago’s buzzing jazz and blues scene, or scream yourself silly on the wild rides and waterslides at the Six Flags amusement park.

More Chicago attractions

Skydeck building in Chicago

Scale the Skydeck

Get an incredible 360-degree view of Chicago from the tallest building in the Western Hemisphere. Feeling brave? Step out on The Ledge, a knee-trembling glass floor, 1353ft up!

Chicago White Sox baseball game

Watch the White Sox

Live the American dream and check out a Baseball game while in town. The U.S. Cellular Field stadium is the home of the famous Chicago White Sox. Home run!

Deep-dish pizza

Delectable delights

Catch a flight to Chicago and taste a real speciality – the deep-dish pizza! Far from the delicate Italian version, it sports a buttery crust up to three inches tall, full of cheese, toppings and sauce.

Shopping district in Chicago

Shop till you drop

Chicago boasts some excellent shopping spots. Stroll the Magnificent Mile, the city’s chic designer destination. Browse the antiques and homeware shops of River North, or hit the hip boutiques of Bucktown.

Chicago city at dusk

Party with a difference

Dance in a converted church at the spectacular Excalibur club, which was once a makeshift morgue, or sample one of 140 kinds of vodka at the aviation-inspired Jet Vodka Lounge.

Explore the Virgin Atlantic blog for more information:

Here's where you'll find hundreds of ideas and recommendations for all of our destinations, including plenty of tips and stories from our staff and crew.

*Fare correct as of 28 April 2016. Bookings must be made at least 90 days in advance. Travel between 17 August 2016 and 28 October 2016.

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Adult passengers are aged 16 and over.

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Young adult passengers aged from 12-15. Young adult passengers travelling alone can't book online - please contact reservations on 0844 209 7777 for help.


Children must be aged 2-11 on the date of their flight.


Infants don't get their own seat on the plane - they'll need the comfort of your lap.

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