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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 Sat, Oct 11 - Sat, Oct 18 THIS IS AN UPDATED VERSION Spirit Airlines $195
Los Angeles Chicago Mon, Sep 22 - Tue, Sep 23 THIS IS AN UPDATED VERSION Spirit Airlines $269
Washington DC Chicago Wed, Oct 8 - Sat, Oct 11 airline logo Frontier Airlines $105
Denver Chicago Tue, Oct 21 - Sat, Oct 25 airline logo Frontier Airlines $155
Boston Chicago Wed, Sep 24 - Sat, Sep 27 THIS IS AN UPDATED VERSION Spirit Airlines $155
San Francisco Chicago Tue, Oct 21 - Tue, Oct 28 airline logo Virgin America $265
Minneapolis Chicago Wed, Oct 1 - Wed, Oct 8 THIS IS AN UPDATED VERSION Spirit Airlines $95
Seattle Chicago Wed, Oct 29 - Sat, Nov 1 airline logo Frontier Airlines $290
Philadelphia Chicago Wed, Oct 1 - Wed, Oct 8 airline logo jetBlue $280
Newark Chicago Tue, Oct 21 - Wed, Oct 22 airline logo jetBlue $226
Portland Chicago Tue, Oct 28 - Sat, Nov 1 THIS IS AN UPDATED VERSION Spirit Airlines $255
Atlanta Chicago Tue, Oct 28 - Tue, Nov 4 airline logo Frontier Airlines $125
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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, Oct 2 - Sat, Oct 4 THIS IS AN UPDATED VERSION Spirit Airlines $205
Los Angeles Chicago Sat, Sep 27 - Sun, Sep 28 THIS IS AN UPDATED VERSION Spirit Airlines $269
Washington DC Chicago Fri, Sep 26 - Sat, Sep 27 airline logo Frontier Airlines $125
Denver Chicago Sat, Sep 20 - Mon, Sep 22 airline logo Frontier Airlines $165
Boston Chicago Sat, Oct 4 - Mon, Oct 6 THIS IS AN UPDATED VERSION Spirit Airlines $165
San Francisco Chicago Fri, Oct 24 - Sat, Oct 25 airline logo Virgin America $285
Minneapolis Chicago Fri, Oct 31 - Sat, Nov 1 THIS IS AN UPDATED VERSION Spirit Airlines $100
Seattle Chicago Fri, Oct 17 - Sat, Oct 18 airline logo Frontier Airlines $309
Philadelphia Chicago Thu, Oct 2 - Mon, Oct 6 airline logo jetBlue $334
Newark Chicago Thu, Oct 2 - Mon, Oct 6 airline logo jetBlue $308
Portland Chicago Sat, Oct 25 - Sun, Oct 26 THIS IS AN UPDATED VERSION Spirit Airlines $265
Atlanta Chicago Fri, Oct 24 - Sun, Oct 26 airline logo Frontier Airlines $185
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