Flights to Chicago

Best Anytime fares to Chicago

Cheap round-trip flights to Chicago

Departure
Arrival
Travel dates
Airline
Round-trip

Departure:

New York

Arrival:

Chicago

Travel dates

Wed, Aug 26 - Wed, Sep 2
airline logo Spirit Airlines

Round-trip

Departure:

Los Angeles

Arrival:

Chicago

Travel dates

Wed, Sep 9 - Sat, Sep 12
airline logo Spirit Airlines

Round-trip

Departure:

Washington DC

Arrival:

Chicago

Travel dates

Mon, Aug 24 - Thu, Aug 27
airline logo Frontier Airlines

Round-trip

Departure:

Denver

Arrival:

Chicago

Travel dates

Wed, Sep 2 - Tue, Sep 15
airline logo United Airlines

Round-trip

Departure:

Boston

Arrival:

Chicago

Travel dates

Thu, Sep 24 - Tue, Sep 29
airline logo Spirit Airlines

Round-trip

Departure:

San Francisco

Arrival:

Chicago

Travel dates

Mon, Aug 24 - Tue, Sep 1
airline logo United Airlines

Round-trip

Departure:

Minneapolis

Arrival:

Chicago

Travel dates

Mon, Aug 17 - Tue, Aug 18
airline logo Spirit Airlines

Round-trip

Departure:

Seattle

Arrival:

Chicago

Travel dates

Tue, Sep 29 - Mon, Oct 5
airline logo United Airlines

Round-trip

Departure:

Philadelphia

Arrival:

Chicago

Travel dates

Fri, Sep 11 - Wed, Sep 16
airline logo Spirit Airlines

Round-trip

Departure:

Newark

Arrival:

Chicago

Travel dates

Tue, Sep 1 - Wed, Sep 9
airline logo United Airlines

Round-trip

Departure:

Portland

Arrival:

Chicago

Travel dates

Sat, Sep 19 - Tue, Sep 22
airline logo Spirit Airlines

Round-trip

Departure:

Atlanta

Arrival:

Chicago

Travel dates

Tue, Aug 25 - Sat, Aug 29
airline logo Spirit Airlines

Round-trip

Best weekend fares to Chicago

Best weekend fares to Chicago

Departure
Arrival
Travel dates
Airline
Round-trip

Departure:

New York

Arrival:

Chicago

Travel dates

Sat, Aug 29 - Mon, Aug 31
airline logo Spirit Airlines

Round-trip

Departure:

Los Angeles

Arrival:

Chicago

Travel dates

Sat, Sep 26 - Sun, Sep 27
airline logo Spirit Airlines

Round-trip

Departure:

Washington DC

Arrival:

Chicago

Travel dates

Fri, Aug 28 - Mon, Aug 31
airline logo Frontier Airlines

Round-trip

Departure:

Denver

Arrival:

Chicago

Travel dates

Fri, Aug 28 - Sun, Aug 30
airline logo United Airlines

Round-trip

Departure:

Boston

Arrival:

Chicago

Travel dates

Thu, Oct 1 - Mon, Oct 5
airline logo Spirit Airlines

Round-trip

Departure:

San Francisco

Arrival:

Chicago

Travel dates

Thu, Sep 24 - Sat, Sep 26
airline logo US Airways

Round-trip

Departure:

Minneapolis

Arrival:

Chicago

Travel dates

Thu, Aug 20 - Sat, Aug 22
airline logo Spirit Airlines

Round-trip

Departure:

Seattle

Arrival:

Chicago

Travel dates

Fri, Sep 11 - Mon, Sep 14
airline logo Sun Country Airlines

Round-trip

Departure:

Philadelphia

Arrival:

Chicago

Travel dates

Fri, Sep 11 - Mon, Sep 14
airline logo Spirit Airlines

Round-trip

Departure:

Newark

Arrival:

Chicago

Travel dates

Fri, Sep 25 - Mon, Sep 28
airline logo United Airlines

Round-trip

Departure:

Portland

Arrival:

Chicago

Travel dates

Sat, Sep 26 - Mon, Sep 28
airline logo Spirit Airlines

Round-trip

Departure:

Atlanta

Arrival:

Chicago

Travel dates

Thu, Aug 27 - Sat, Aug 29
airline logo Spirit Airlines

Round-trip

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.

  

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Airports in Chicago IL, US

Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

    Carriers

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Carriers