United States

Cheap flights to Chicago

The cheapest round trip to Chicago we found today is $167 from Miami, for travel in November 2026. We check fares to Chicago from 7 cities twice a day.

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Airports: ORD · MDW
Currency: US Dollar (USD)
Local time: UTC−6
Languages: English
Best time to visit: May, June, September, and October
Cities we check: 7 cities

About Chicago

Chicago is famous for its architecture, best seen on a river boat tour, plus deep-dish pizza, blues and jazz clubs and the lakefront. O'Hare (ORD) is a major hub with flights almost everywhere, and Midway (MDW) adds low-cost options.

Cheapest fares to Chicago by city

Cheapest round trip per city, from fares seen on November 11, 2026.

Cheapest months to fly to Chicago from Miami

The cheapest round trip we found for each departure month.

Nov 2026$167 (Cheapest)
Dec 2026$372
Jan 2027$212

Questions about flights to Chicago

How much is a flight to Chicago?

The cheapest round trip to Chicago we found today is $167 from Miami, for travel in November 2026. Fares from other cities are in the table above and change every day.

What is the cheapest month to fly to Chicago?

From Miami, November 2026 is the cheapest month right now at $167 round trip. The most expensive is December 2026, at $372.

Are there cheap nonstop flights to Chicago?

Yes. Some of the cheapest fares we found were nonstop, from Miami, Los Angeles, New York, and Madrid.

When is the best time to visit Chicago?

May, June, September, and October usually bring the most pleasant weather in Chicago, often with shoulder-season fares outside the peak holidays.

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