Flights to Chicago

Best Anytime fares to Chicago

Cheap round-trip flights to Chicago

Departure Arrival Travel dates Airline Round-trip
Boston Chicago Tue, Sep 29 - Tue, Oct 6 THIS IS AN UPDATED VERSION Spirit Airlines $81
Newark Chicago Thu, Oct 1 - Mon, Oct 5 Delta Airlines Delta Air Lines $188
Philadelphia Chicago Mon, Oct 26 - Sat, Oct 31 new F9 logo Frontier Airlines $79
Portland Chicago Wed, Sep 30 - Tue, Oct 6 THIS IS AN UPDATED VERSION Spirit Airlines $197
Denver Chicago Sat, Oct 24 - Mon, Oct 26 THIS IS AN UPDATED VERSION Spirit Airlines $81
Portland Chicago Thu, Sep 3 - Sat, Sep 5 THIS IS AN UPDATED VERSION Spirit Airlines $197
Atlanta Chicago Thu, Oct 1 - Sat, Oct 3 new F9 logo Frontier Airlines $58
Washington DC Chicago Thu, Sep 17 - Mon, Sep 21 new F9 logo Frontier Airlines $58
Seattle Chicago Wed, Sep 23 - Wed, Oct 7 airline logo United Airlines $276
Philadelphia Chicago Thu, Oct 22 - Sun, Oct 25 THIS IS AN UPDATED VERSION Spirit Airlines $81
Los Angeles Chicago Mon, Sep 21 - Wed, Sep 23 new F9 logo Frontier Airlines $99
Denver Chicago Wed, Sep 30 - Tue, Oct 6 new F9 logo Frontier Airlines $81
New York Chicago Tue, Sep 29 - Wed, Sep 30 THIS IS AN UPDATED VERSION Spirit Airlines $81
San Francisco Chicago Sat, Oct 3 - Mon, Oct 5 new F9 logo Frontier Airlines $138
Minneapolis Chicago Sat, Oct 10 - Sun, Oct 11 THIS IS AN UPDATED VERSION Spirit Airlines $87
Boston Chicago Fri, Oct 23 - Sat, Oct 24 THIS IS AN UPDATED VERSION Spirit Airlines $81
Newark Chicago Tue, Oct 13 - Tue, Oct 20 airline logo United Airlines $166
Washington DC Chicago Tue, Sep 15 - Mon, Sep 21 new F9 logo Frontier Airlines $58
Atlanta Chicago Tue, Oct 6 - Wed, Oct 7 new F9 logo Frontier Airlines $58
New York Chicago Thu, Sep 17 - Mon, Sep 21 THIS IS AN UPDATED VERSION Spirit Airlines $107
Seattle Chicago Fri, Sep 25 - Sat, Sep 26 airline logo Sun Country Airlines $284
Minneapolis Chicago Mon, Sep 14 - Tue, Sep 22 airline logo Sun Country Airlines $81
Los Angeles Chicago Thu, Oct 22 - Mon, Oct 26 new F9 logo Frontier Airlines $105
San Francisco Chicago Wed, Sep 30 - Mon, Oct 5 new F9 logo Frontier Airlines $138
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Best weekend fares to Chicago

Best weekend fares to Chicago

Departure Arrival Travel dates Airline Round-trip
Newark Chicago Thu, Oct 1 - Mon, Oct 5 Delta Airlines Delta Air Lines $188
Boston Chicago Fri, Oct 23 - Sat, Oct 24 THIS IS AN UPDATED VERSION Spirit Airlines $81
Denver Chicago Sat, Oct 24 - Mon, Oct 26 THIS IS AN UPDATED VERSION Spirit Airlines $81
Portland Chicago Thu, Sep 3 - Sat, Sep 5 THIS IS AN UPDATED VERSION Spirit Airlines $197
Atlanta Chicago Thu, Oct 1 - Sat, Oct 3 new F9 logo Frontier Airlines $58
New York Chicago Thu, Sep 17 - Mon, Sep 21 THIS IS AN UPDATED VERSION Spirit Airlines $107
Washington DC Chicago Thu, Sep 17 - Mon, Sep 21 new F9 logo Frontier Airlines $58
Seattle Chicago Fri, Sep 25 - Sat, Sep 26 airline logo Sun Country Airlines $284
Philadelphia Chicago Thu, Oct 22 - Sun, Oct 25 THIS IS AN UPDATED VERSION Spirit Airlines $81
Los Angeles Chicago Thu, Oct 22 - Mon, Oct 26 new F9 logo Frontier Airlines $105
Minneapolis Chicago Sat, Oct 10 - Sun, Oct 11 THIS IS AN UPDATED VERSION Spirit Airlines $87
San Francisco Chicago Sat, Oct 3 - Mon, Oct 5 new F9 logo Frontier Airlines $138
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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 International Airport (ORD)

    Distance from City Center: 15.1 miles