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Cheap Flights to Chicago
| Most popular in | January | High demand for flights, 3% potential price rise |
| Cheapest in | February | Best time to find cheap flights, 2% potential price drop |
| Average price | $1,719 | Price for this month |
| Cheapest price | $1,440 | From Auckland to Chicago |
Cheapest prices for Chicago flights by month
January
$2,101
February
$1,113
March
$1,517
April
$2,101
May
$1,823
June
$1,941
July
$1,986
August
$1,851
September
$1,719
October
$1,722
November
$1,673
December
$2,068
Currently, February is the cheapest month in which you can book a flight to Chicago. Flying to Chicago in January will prove the most costly. There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
When is the best time to fly to Chicago?
Choose a month below to see average flight price and weather conditions.
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 flights 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.
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Which day is cheapest to fly to Chicago?
The cheapest flights to Chicago are usually found when departing on a Tuesday. The departure day with the highest cost at present is Sunday.
What time of day is cheapest to fly?
Chicago flights can be made cheaper if you choose a flight in the morning. Booking a flight in the evening will likely mean higher prices.
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.