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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 Wed, Jun 11 - Tue, Jun 17 airline logo Spirit Airlines $208
Los Angeles Chicago Mon, May 12 - Tue, May 13 airline logo Spirit Airlines $274
Washington DC Chicago Tue, May 6 - Tue, May 20 airline logo JetBlue Airways $220
Denver Chicago Mon, May 12 - Tue, May 13 airline logo Spirit Airlines $174
Boston Chicago Wed, Jun 4 - Tue, Jun 10 airline logo Spirit Airlines $158
San Francisco Chicago Wed, May 28 - Wed, Jun 4 airline logo Alaska Airlines $318
Minneapolis Chicago Wed, Apr 23 - Tue, Apr 29 airline logo Spirit Airlines $72
Seattle Chicago Sat, May 3 - Tue, May 6 airline logo Frontier Airlines $307
Philadelphia Chicago Mon, May 5 - Thu, May 8 airline logo United Airlines $270
Newark Chicago Mon, May 19 - Tue, May 20 airline logo United Airlines $233
Portland Chicago Sat, May 24 - Sun, Jun 1 airline logo Spirit Airlines $218
Atlanta Chicago Tue, May 6 - Wed, May 7 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 Fri, Jun 6 - Sat, Jun 7 airline logo Spirit Airlines $228
Los Angeles Chicago Thu, May 29 - Sat, May 31 airline logo Spirit Airlines $288
Washington DC Chicago Sat, May 3 - Sun, May 4 airline logo United Airlines $215
Denver Chicago Sat, May 10 - Sun, May 11 airline logo Spirit Airlines $174
Boston Chicago Thu, May 8 - Mon, May 12 airline logo United Airlines $186
San Francisco Chicago Thu, May 1 - Sat, May 3 airline logo Sun Country Airlines $320
Minneapolis Chicago Thu, Jun 12 - Mon, Jun 16 airline logo Spirit Airlines $88
Seattle Chicago Fri, May 9 - Mon, May 12 airline logo Sun Country Airlines $312
Philadelphia Chicago Sat, May 24 - Mon, May 26 airline logo United Airlines $270
Newark Chicago Sat, Apr 26 - Mon, Apr 28 Delta Airlines Delta Air Lines $288
Portland Chicago Thu, Jun 5 - Mon, Jun 9 airline logo Spirit Airlines $218
Atlanta Chicago Thu, May 8 - Sat, May 10 airline logo United Airlines $280
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