By clicking, I agree to the terms

Cheap Flights to Chicago

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

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, Sep 3 - Sat, Sep 6 airline logo Spirit Airlines $185
Los Angeles Chicago Mon, Sep 15 - Tue, Sep 16 airline logo American Airlines $213
Washington DC Chicago Mon, Sep 22 - Thu, Sep 25 airline logo Frontier Airlines $105
Denver Chicago Tue, Aug 19 - Wed, Aug 27 airline logo Spirit Airlines $125
Boston Chicago Sat, Sep 20 - Tue, Sep 23 airline logo Spirit Airlines $155
San Francisco Chicago Thu, Sep 4 - Fri, Sep 5 airline logo Virgin America $265
Minneapolis Chicago Wed, Sep 17 - Wed, Oct 1 airline logo Spirit Airlines $79
Seattle Chicago Thu, Sep 4 - Tue, Sep 9 airline logo Frontier Airlines $310
Philadelphia Chicago Wed, Sep 3 - Wed, Sep 10 airline logo jetBlue $289
Newark Chicago Wed, Sep 3 - Wed, Sep 10 airline logo jetBlue $242
Portland Chicago Tue, Aug 26 - Tue, Sep 2 airline logo Spirit Airlines $225
Atlanta Chicago Thu, Aug 21 - Fri, Aug 22 airline logo AirTran Airways $237
Back to menu Return to top

Best weekend fares to Chicago

Best weekend fares to Chicago

Departure Arrival Travel dates Airline Round-trip
New York Chicago Thu, Sep 11 - Sat, Sep 13 airline logo Spirit Airlines $195
Los Angeles Chicago Thu, Sep 4 - Mon, Sep 8 Delta Airlines Delta Air Lines $237
Washington DC Chicago Fri, Sep 19 - Sat, Sep 20 airline logo Frontier Airlines $105
Denver Chicago Thu, Aug 28 - Sat, Aug 30 airline logo Spirit Airlines $145
Boston Chicago Sat, Sep 13 - Mon, Sep 15 airline logo Spirit Airlines $170
San Francisco Chicago Sat, Sep 13 - Mon, Sep 15 airline logo AirTran Airways $282
Minneapolis Chicago Thu, Sep 11 - Sat, Sep 13 airline logo Spirit Airlines $92
Seattle Chicago Fri, Sep 12 - Mon, Sep 15 airline logo Frontier Airlines $310
Philadelphia Chicago Thu, Sep 25 - Sat, Sep 27 airline logo jetBlue $300
Newark Chicago Sat, Sep 6 - Mon, Sep 8 airline logo jetBlue $258
Portland Chicago Thu, Sep 11 - Sat, Sep 13 airline logo Spirit Airlines $240
Atlanta Chicago Fri, Aug 22 - Sat, Aug 23 airline logo AirTran Airways $278
Back to menu Return to top