Cheap Flights to Chicago

Chicago overview

When is the best time to fly?

Chicago’s seasons are intense – it’s hot in the summer and cold in the winter – but savvy travellers can always find cheap flights to Chicago.

Peak Season:

Summer is between June and August and it is the peak of the festival season in the Chicago area with major events taking place in the parks and neighbourhoods every weekend, in spite of the heat and humidity from the Lake. Taste of Chicago, taking place mid-July at the lakefront is an outdoor food festival which showcases the variety of cuisines and local flavours accompanied by live music. If book a flight to Chicago during its most popular festival, expect crowds of visitors in the area and a rise in flight prices. 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 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.

Why visit Chicago?

Book a flight to Chicago and visit a skyscraper metropolis and a feat of modern architecture as well as home to what was once the world’s tallest building, Sears Tower. Chicago may not be a traditional tourist destination but you will find that the Second City is well worth a visit. As the hub of the Midwest, Chicago is not to be overlooked. Its picturesque skyline is reflected in the waters of Lake Michigan. World-class museums of art and science, fine public art, huge parks and sandy beaches and a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups) make it an unbeatable destination for a holiday. First stop should be the lakefront, from Lakeview to Oak Street Beach, the entire area is bustling for things for you to do and to see. Whatever your passion, Chicago will match it.

Chicago has long been thought of as the nation's second city - indeed, Chicagoans only grudgingly admit that New York occupies first place. The city's central area, including the Loop and the Magnificent Mile, is famous for its combination of modern and historic architecture. Chicago is also home to many of the country's best museums and art galleries, including the Field Museum of Science and Industry and, reflecting the city's industrial heritage, the Museum of Science and Industry.

Chicago climate

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.

Getting around Chicago

Chicago's regular, grid-like layout makes navigation straightforward, but the "City With Big Shoulders" can be a little too large to get around easily on foot. Fortunately, the city's public transportation system, including the famous "L" (short for "elevated train tracks"), is efficient, with especially good coverage in the city centre area. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Cycling is a popular way to get around and with all of Chicago’s lakefront property, it can be a great way to enjoy the city.

Getting to the city

Flights to Chicago land at O'Hare International Airport (ORD) located in the city's northwest corner, about 17 miles away from the Loop. 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.

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Prices found by our users for local departures to Chicago

Airports for Chicago

Cheapest flights to USA

How much do things cost in Chicago?

Transport
Petrol (1 litre)
£ 0.55
One-way ticket (local transport)
£ 1.60
1 mile taxi journey
£ 1.16
Taxi - fixed fee
£ 2.08
Markets
Large bottle of water
£ 1.26
Bottle of local beer (0.5 litre)
£ 0.92
Bottle of beer (imported beer)
£ 1.27
Loaf of white bread
£ 1.52
Clothing & Shoes
Pair of Nike trainers
£ 55.23
Pair of jeans
£ 29.50
Restaurants
Imported beer (0.33 litre)
£ 3.84
Small bottle of water (0.33 litre)
£ 1.02
Local draught beer (0.5 litre)
£ 2.56
Coke/Pepsi (0.33 litre)
£ 1.07
How much does an apartment cost in Chicago?
1 bedroom flat in city centre
£ 1017
3 bedroom flat in city centre
£ 2004
1 bedroom flat outside of centre
£ 626
3 bedroom flat outside of centre
£ 1359

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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