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Cheap Flights to Chicago

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Chicago flights

Bargain flights to Chicago are a good way to get you into a city that is full of art, culture, and history.

Flights to Chicago

Generally, flights to Chicago land at O'Hare International Airport, although Midway International Airport is gaining popularity. Midway International is located just 10 miles from the downtown center, and there are shuttle buses to hotels as well as the Transit Authority's Orange Line. Chicago flights that land at O'Hare International Airport put you about 17 miles northwest of the city, and transportation options include regional trains and buses, car rentals, and transit lines. Music in the terminals is listed and you can log into the airport website to find out exactly what you were hearing! Just be aware that if you do this from the airport, the available Wi-Fi is charged at $6.95 a day.

Chicago Weather

The term "Windy City" may actually refer to politicians' speeches, but that doesn't change the fact that the weather is often blustery. Whenever you visit, you will want to keep a jacket on hand for the lake breezes. Weather becomes nasty between November and March, especially in January, when temperatures drop to 24°F (-4°C), and are emphasized by that ubiquitous wind, as well as snow! Plan for indoor activities if you visit during this time period! You'll probably prefer the weather between April and October, when everyone rushes outside. During the peak tourist season, temperatures hover around 85°F (29°C).

Getting Around Chicago

Driving in downtown Chicago is a hassle best avoided. Traffic is overwhelming, pedestrians often don't follow the rules of the road, parking spaces are expensive, and tickets and towing are strict for violations, especially in the snow! The best way to get around Chicago is public transit. With several different agencies in the Chicago area all overseen by the RTA (Regional Transportation Authority), you can plan trips online with their planner. Once your Chicago flights have landed, navigating the city is easy. The city is consistent in street numbering and block lengths and organized on a grid that is easy to get used to. There are, however, some notable exceptions, avenues like Milwaukee and Ogden that go diagonally or meander through the city.

Chicago Attractions

Chicago is a bustling city, with many things to do and see within its city limits. Explore the arts, the night life, and even some natural areas to keep busy. Below are some suggestions to get you started:

  • The Adler Planetarium, with astronomy shows and neat interactive space exhibits.
  • DuSable Museum of African American History, with exhibits of the history and achievements of people of African descent in Chicago.
  • Rogers Park beach, with miles of sand to remind you that you're on the largest freshwater lake entirely in the United States.
  • Shedd Aquarium, with exhibits that cover the Caribbean and the Pacific Northwestern United States.
  • Milennium Park, with ice skating, cultural programs, and exhibitions in the new Chicago town square.
Best Anytime fares to Chicago

Cheap round-trip flights to Chicago

Departure Arrival Travel dates Airline Round-trip
New York Chicago Tue, May 13 - Wed, May 14 airline logo Spirit Airlines $188
Los Angeles Chicago Tue, May 13 - Sat, May 24 airline logo Spirit Airlines $268
Washington DC Chicago Tue, Jun 17 - Wed, Jun 25 airline logo JetBlue Airways $226
Denver Chicago Tue, May 20 - Wed, May 21 airline logo Spirit Airlines $164
Boston Chicago Tue, May 6 - Tue, May 13 airline logo Spirit Airlines $148
San Francisco Chicago Tue, May 20 - Wed, May 28 airline logo United Airlines $278
Minneapolis Chicago Tue, May 6 - Wed, May 7 airline logo Spirit Airlines $72
Seattle Chicago Sun, May 25 - Sat, May 31 airline logo Frontier Airlines $313
Philadelphia Chicago Wed, Jun 18 - Wed, Jun 25 airline logo JetBlue Airways $283
Newark Chicago Sat, Apr 26 - Tue, Apr 29 airline logo United Airlines $221
Portland Chicago Wed, May 28 - Mon, Jun 9 airline logo Spirit Airlines $238
Atlanta Chicago Mon, May 19 - Tue, May 20 airline logo AirTran Airways $211
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Best weekend fares to Chicago

Best weekend fares to Chicago

Departure Arrival Travel dates Airline Round-trip
New York Chicago Thu, May 1 - Sat, May 3 airline logo Spirit Airlines $208
Los Angeles Chicago Thu, May 8 - Sat, May 10 airline logo Spirit Airlines $268
Washington DC Chicago Thu, Jun 5 - Sat, Jun 7 airline logo JetBlue Airways $226
Denver Chicago Thu, May 8 - Mon, May 12 airline logo Spirit Airlines $188
Boston Chicago Thu, May 8 - Mon, May 12 airline logo Spirit Airlines $168
San Francisco Chicago Fri, May 30 - Sat, May 31 airline logo Virgin America $323
Minneapolis Chicago Thu, Jun 12 - Mon, Jun 16 airline logo Spirit Airlines $88
Seattle Chicago Fri, May 9 - Sun, May 11 airline logo Sun Country Airlines $322
Philadelphia Chicago Thu, May 8 - Sat, May 10 airline logo United Airlines $314
Newark Chicago Sat, Apr 26 - Mon, Apr 28 airline logo United Airlines $221
Portland Chicago Sat, May 24 - Sun, May 25 airline logo Spirit Airlines $238
Atlanta Chicago Thu, May 8 - Mon, May 12 airline logo AirTran Airways $280
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