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Cheap Flights to Chicago

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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 flight tickets 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. Fly to Chicago’s most popular festival so expect crowds of visitors in the area and 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.

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

  • Taste of Chicago 

The nation's premier outdoor food festival showcasing the diversity of Chicago's dining community. The delicious array of food served at Taste of Chicago is complemented by music and exciting activities for the entire family. Every summer since 1980, Chicago's beautiful Grant Park on the city's magnificent lakefront has been home to the world's largest food festival.

  • The Chicago Air and Water Show

 Presented by Shell Oil Products U.S. and the City of Chicago is the largest FREE show of its kind in the United States. The show can be viewed along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point. 

  • Chicago Marathon 
  • Venetian Nights

Almost every year since the event first began in 1958, Chicago has come together to celebrate and take in the amazing displays of Venetian Night. 

Due to the economic downturn, Venetian Night has been cancelled in recent years, but returned in 2013 better than ever at a new venue at the 31st Street Harbor!

Originally, Venetian Night was just a part of the Chicago Lakefront festival that celebrated everything wet and wild about the city. With the Lakefront Festival eventually scrapped, the boat parade proved so popular that it lived on in Venetian Night as an established part of the Chicago festivities calendar, sponsored by the Chicago Yachting Association. Venetian Night in Chicago is the oldest event sponsored by the city. It is both named and modelled after the ever popular boat parades in Venice, which are typically a Christmas event in Venice, while the Chicago Venetian Night is a summer festival. 

Why visit Chicago?

Chicago is 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 to the cityChicago's major airport is 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.

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.

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Useful information about Chicago

Photo of Chicago   Chicago
Avg temperature for this monthChicago17.5 °CSource: World Weather Online
Average monthly rainfall inChicago66 mmSource: World Weather Online
Average flight time toChicago8 hrs 33 mins
Rate of exchange inChicago$1.00 = £0.62Source: Oanda
Airlines that fly toChicagoFinnair, US Airways and Tap Air Portugal
Deals available on flights toChicago1867
Advertisers with deals toChicagoClickaflight, Airbookers and One2One Flights
Advertisers with deals toChicago37
Lowest flight deal toChicago£401
Average flight offer toChicago£693

 How much do things cost in Chicago?

  • One-way ticket (local transport): £1.40
  • A dozen eggs: £1.29
  • Pair of jeans: £27.78
  • 3 course meal for 2: £34.19
  • 1 mile taxi journey: £1.24
  • Bottle of wine: £7.77
  • 1 litre of milk: £0.56
  • Bottle of local beer (0.5 litre): £1.52
  • Small bottle of water (0.33 litre): £0.91
  • 1 bedroom flat outside of centre: £608.48