Cheap Flights to Chicago

Chicago overview

When is the best time to fly?

Peak Season:

Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the Lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighbourhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals.

Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavours accompanied by live music. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.

September can be the most enjoyable and mild month of the year but there's less going on during this period.

Off-peak Season:

January to March is when Chicago is least busy, making cheap flights to Chicago and hotel deals more 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.

Chicago insider information

One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don't expose skin to the wind; in summer, be sure to drink plenty of water and use sunscreen.

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Prices found by our users for local departures to Chicago

Airports for Chicago

How much do things cost in Chicago?

Clothing & Shoes
Pair of Nike shoes
C$ 102.44
Pair of jeans
C$ 64.87
3 course meal for 2
C$ 81.06
Coke/Pepsi (0.33 litre)
C$ 2.55
Imported beer (0.33 litre)
C$ 8.11
Small bottle of water (0.33 litre)
C$ 2.17
Bottle of beer (imported beer)
C$ 2.33
Large bottle of water
C$ 2.58
Bottle of wine
C$ 20.27
Bottle of local beer (0.5 litre)
C$ 2.05
How much does transport cost in Chicago?
One-way ticket (local transport)
C$ 3
1 km taxi journey
C$ 2
Taxi - fixed fee
C$ 4
Petrol (1 litre)
C$ 1

International departures to Chicago