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Flights to Chicago

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Best Anytime fares to Chicago

Cheap round-trip flights to Chicago

Departure Arrival Travel dates Airline Round-trip
New York Chicago Tue, Feb 3 - Wed, Feb 4 THIS IS AN UPDATED VERSION Spirit Airlines $87
Los Angeles Chicago Tue, Feb 10 - Tue, Feb 17 airline logo American Airlines $237
Washington DC Chicago Wed, Feb 11 - Fri, Feb 20 new F9 logo Frontier Airlines $105
Denver Chicago Tue, Feb 10 - Tue, Feb 17 THIS IS AN UPDATED VERSION Spirit Airlines $97
Boston Chicago Wed, Feb 4 - Sat, Feb 7 airline logo American Airlines $133
San Francisco Chicago Wed, Mar 4 - Tue, Mar 10 airline logo Sun Country Airlines $244
Minneapolis Chicago Mon, Mar 2 - Sat, Mar 14 THIS IS AN UPDATED VERSION Spirit Airlines $81
Seattle Chicago Tue, Mar 3 - Wed, Mar 4 new F9 logo Frontier Airlines $289
Philadelphia Chicago Tue, Mar 24 - Tue, Mar 31 THIS IS AN UPDATED VERSION Spirit Airlines $244
Newark Chicago Mon, Feb 2 - Sat, Feb 14 airline logo American Airlines $177
Portland Chicago Mon, Mar 9 - Wed, Mar 11 THIS IS AN UPDATED VERSION Spirit Airlines $278
Atlanta Chicago Tue, Feb 3 - Wed, Feb 4 new F9 logo Frontier Airlines $78
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Best weekend fares to Chicago

Best weekend fares to Chicago

Departure Arrival Travel dates Airline Round-trip
New York Chicago Sat, Feb 28 - Mon, Mar 2 THIS IS AN UPDATED VERSION Spirit Airlines $97
Los Angeles Chicago Thu, Feb 26 - Mon, Mar 2 THIS IS AN UPDATED VERSION Spirit Airlines $237
Washington DC Chicago Sat, Feb 28 - Mon, Mar 2 new F9 logo Frontier Airlines $105
Denver Chicago Sat, Feb 7 - Mon, Feb 9 airline logo American Airlines $97
Boston Chicago Thu, Feb 5 - Sat, Feb 7 airline logo United Airlines $133
San Francisco Chicago Thu, Feb 19 - Mon, Feb 23 airline logo Sun Country Airlines $244
Minneapolis Chicago Thu, Feb 26 - Sat, Feb 28 THIS IS AN UPDATED VERSION Spirit Airlines $81
Seattle Chicago Fri, Feb 27 - Sat, Feb 28 airline logo American Airlines $329
Philadelphia Chicago Fri, Feb 27 - Mon, Mar 2 airline logo United Airlines $261
Newark Chicago Sat, Feb 7 - Mon, Feb 9 airline logo American Airlines $177
Portland Chicago Fri, Feb 27 - Mon, Mar 2 new F9 logo Frontier Airlines $298
Atlanta Chicago Sat, Feb 21 - Mon, Feb 23 new F9 logo Frontier Airlines $78
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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.
  • Chicago When to Go

    Come summer, Chicagoans head to the beaches, parks, and festivals along Lake Michigan. A chill often lingers in the air in early summer, while late summer can be muggy. Regardless of the season, pack layers, as weather can fluctuate greatly. Summer also brings spikes in hotel rates.

    Fall is pleasant until mid-November, when temperatures plunge, and spring doesn’t get reliably comfortable until late April. Anytime between May and November, you’ll be able to combine season-less indoor attractions with the convivial appeal of the outdoors at the lakefront, on Chicago River boats, and milling around Millennium Park.

    Weather and prices are tradeoffs in Chicago. In January and February, the “hawk” (a local term for the harsh wind off Lake Michigan) sweeps down Michigan Avenue, and snow buries the streets. But hotel rates are bargain basement and attractions uncrowded.

Airports in Chicago IL, US

map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles