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Cheap Flights from Boston to Chicago
BOS → CHI • About 2h 40m nonstop • 4 airlines
Adults
+12 years old
Children
2-11 years old
Infants
Under 2 years
Fares shown are the lowest we have recorded recently on this route and are not a live quote. Run a search above for today's availability, or call (800) 399-8818 and an agent will price it with you.
Flights from Boston (BOS) to Chicago (CHI)
The Boston to Chicago route covers roughly 850 miles and takes about 2h 40m nonstop. 4 airlines compete on it — United Airlines, American Airlines, JetBlue Airways, Delta Air Lines — which keeps fares moving and makes it worth comparing carriers rather than defaulting to the one you usually fly. We have seen one-way fares on this route start around $98.
Chicago earns its architecture reputation the moment you look up. The city invented the skyscraper and has spent 130 years refining it, and a river cruise past the Loop remains the single best introduction to the place.
It is also one of the great American eating cities — deep dish is the tourist headline, but the Italian beef, the Mexican food in Pilsen, and the fine dining in West Loop are what locals actually argue about.
Airlines flying BOS to CHI
- United Airlines
- American Airlines
- JetBlue Airways
- Delta Air Lines
Airports on this route
- Departing: Boston Logan International Airport (BOS)
- Arriving: Chicago O'Hare International Airport (ORD)
- Arriving: Chicago Midway International Airport (MDW)
Best time to fly to Chicago
May through October. September and early October deliver the best combination of warm days, thin crowds and moderate fares.
Top things to do in Chicago
- Millennium Park and Cloud Gate
- Art Institute of Chicago
- Chicago Riverwalk
- Navy Pier
- Willis Tower Skydeck
- Wrigley Field
- Museum Campus
How to save on Boston to Chicago flights
- Shift your departure by one or two days — midweek departures on this route are consistently cheaper than Friday and Sunday.
- Book four to eight weeks ahead. Last-minute fares on BOS to CHI routinely run double the advance price.
- Compare all 4 carriers rather than checking one airline's own site.
- Midway is closer to downtown than O'Hare and usually cheaper on Southwest-served routes.
- The lakefront is genuinely cold and windy well into May — pack a layer even in spring.
- January and February fares into Chicago are the lowest of the year by a wide margin.
About flights from Boston to Chicago
Fares on the BOS to CHI route move with demand, so flexibility is worth more than timing tricks. Shifting your departure by a day or two, flying midweek instead of Friday or Sunday, and booking four to eight weeks ahead all reduce the fare on this route. Our agents also hold consolidator and unpublished fares that do not appear in online results.
United Airlines, American Airlines, JetBlue Airways, Delta Air Lines all operate on this route. United Airlines typically offers the most frequencies, with American Airlines and JetBlue Airways providing competing schedules. Availability varies by season and by which Boston airport you depart from, so it is worth comparing all carriers before booking.
A nonstop flight takes about 2h 40m. Itineraries with a connection typically add two to four hours depending on the layover city and the length of the stop.
The two cities are roughly 850 miles apart by air.
Departures leave from Boston Logan International Airport (BOS). Arrivals land at Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW).
May through October. September and early October deliver the best combination of warm days, thin crowds and moderate fares.