Cheap Flights to Chicago

Chicago overview

When is the best time to fly to Chicago?

Peak season:

If you’ve been to New York then why not book cheap flights to Chicago, the nation’s second city? The skyscraper metropolis is a feat of modern architecture, as well as home to what was once the world’s tallest building, Sears Tower. It is not a traditional tourist destination but as the hub of the Midwest, Chicago much to offer as a holiday destination. Featuring world-class art galleries and science museums, huge parks and sandy beaches, it also has a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups). Peak tourist season is summer (June to August). This coincides with the festival season with many major events taking place in Chicago parks and neighbourhoods every weekend, in spite of the heat and humidity. Taste of Chicago, an outdoor food festival which showcases the variety of cuisines and local flavours, is in mid-July at the lakefront. If you book flights to Chicago during this popular festival, expect crowds of visitors in the area and a rise in the price of flight tickets. August is host to another popular event – the Chicago Air and Water Show. With its free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.

Off season:

Chicago is least busy in January through March making cheap flights to Chicago and hotel deals attainable. However, true to its reputation as the ‘Windy City’, cold temperatures and brisk winds will make you want to stay inside for most of your visit.

When is the best time to book a flight to Chicago?

Savvy travellers are always on the lookout for the cheapest flights to Chicago but one of the biggest challenges for figuring out when to go can be the weather. If you don’t enjoy extreme temperatures, fiercely hot summers and bitterly cold winters, then give these two seasons a miss. April through May or September through October are the most enjoyable and mild months of the year in Chicago. You’ll still get warm weather and the hotel rates are more reasonable.

How long is the flight to Chicago?

Flights from London to Chicago: 8 hours 50 minutes.

Flights from Manchester to Chicago: 8 hours 40 minutes.

Flights from Birmingham to Chicago: 10 hours 30 minutes.

Flights from Glasgow to Chicago: 10 hours 10 minutes.

Which airlines operate flights to Chicago?

There are plenty of direct daily flights to Chicago departing from London Heathrow with airlines such as British Airways, United Airlines and Virgin Atlantic. Connecting flights with various European airlines are available but will add a couple of hours to the flight time. The quickest direct flight to Chicago from Manchester is with American Airlines. Flights from other UK cities will require a connecting flight.

How to get from the airport to the city centre?

Flights to Chicago land at O'Hare International Airport (ORD) located in the city's northwest corner, about 17 miles away from the CBD or Chicago Loop. Trains and buses provide efficient transportation to city centre and suburbs. The Blue Line of the Chicago subway (known as the 'L' to locals) connects O'Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available from the airport.

Chicago insider information

  • Before you arrive in Chicago, familiarise yourself with this handy airport guide for a smoother transition.
  • Whether you're in Chicago for a for days or weeks, here's a fun 24-hour guide for sightseeing, eating and shopping!
  • Calling all theatre-lovers, Chicago's downtown scene is bustling with live entertainment which is why it's made the top ten cities for live theatre list.
  • Chicago's festive cocktails come back into vogue during the winter months. Here are 7 places in the city you can sip on more than just eggnog this Christmas.

Find the best prices for you!

Prices found by our users for South African departures to Chicago

Airports for Chicago

Cheapest flights to USA

How much do things cost in Chicago?

Coke/Pepsi (0.33 litre)
R 27.79
R 59.62
One-way ticket (local transport)
R 35.11
Petrol (1 litre)
R 11.45
1 km taxi journey
R 17.45
Taxi - fixed fee
R 50.71
Clothing & Shoes
Pair of jeans
R 742.07
Pair of Nike shoes
R 1301.97
Loaf of white bread
R 42.10
Large bottle of water
R 27.57
Pack of Marlboro cigarettes
R 171.63
How much does a beer cost in Chicago?
Bottle of beer (imported beer)
R 29
Local draught beer (0.5 litre)
R 78
Bottle of local beer (0.5 litre)
R 21
Imported beer (0.33 litre)
R 94

More information about Chicago

  • Treat yourself one evening to a show at Chicago’s renowned McCormick Place or Chicago Theatre
  • The third-largest city in the USA, Chicago has plenty for anyone wanting an exciting American city break
  • Spend your evenings enjoying live blues and jazz bands in Chicago’s legendary lounge bars
  • Make your way up to the 103rd floor of the Willis Tower (previously Sears Tower) for amazing views out across the city
  • Let the kids enjoy meeting countless birds and animals at magnificent Lincoln Park Zoo in the city centre
  • Watch out for great deals on one way flights to Chicago and then get domestic flights to anywhere across the US
  • Book direct flights to Chicago now, and enjoy a trip to one of America’s most vibrant and entertaining cities
  • Relax after a day’s sightseeing in Lincoln Park – the city’s largest, and second most visited in the US
  • Have a wander around the magnificent shops and boutiques along Chicago’s State Street and the ‘Magnificent Mile’
  • In the summer, relax on one of Chicago’s 33 golden beaches that stretch along the waterfront

International departures to Chicago