The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Boston to Chicago

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the beginning of December. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.

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week: 7 Dec - 13 Dec

Flights from just £82

£102

£98

£94

£120

£115

£82

£119

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NovemberDecemberJanuary

Flight Duration3 h and 17 mFlights between Boston and Chicago take, on average, 3 h and 17 m minutes, but the time can vary according to other factors

Cheapest flight£95Cheapest price for a flight between Boston and Chicago found by our customers in the last 72 hours

Origin airportLogan International AirportWhen flying from Boston to Chicago

High seasonMarchAccording to search data from our customers, March is the busiest time to fly from Boston to Chicago

Airlines flying this routeAmerican AirlinesAirline(s) with flights between Boston to Chicago

One-way average Price£115The average price for a flight Boston - Chicago at Opodo is £115, based on the price of last 6 months

Best time to bookOctoberAccording to real data May is the most popular time to book a flight to Chicago when departing from Boston

Airlines that fly from Boston to Chicago

American Airlines

471£

United Airlines

Distance: 854 mi

Boston airports

Logan International Airport (BOS)How far from city centre: 3 mi

Chicago airports

O'hare International Airport (ORD)How far from city centre: 13 mi

Book your Boston to Chicago flight

Search direct and connecting flights from Boston to Chicago (United States) with Opodo. When your results appear, sort them by timing or fare and book whichever option fits your plans best.

The cheapest fare booked on this route in recent days was £95, although the price you're shown will vary with your travel dates and departure times.

Flying non-stop from Boston to Chicago takes roughly 3 h and 4 m, whereas journeys with a layover will take longer.

Airports and airlines on the Boston–Chicago route

Plan your trip with confidence by checking the relevant airports and comparing the airlines that fly this route.

Departure airport: Logan International Airport (BOS)
Arrival airport: O'hare International Airport (ORD)

The weather in Chicago

The best time to go may come down to the kind of weather you most enjoy. In Chicago, temperatures average around 28ºC in the warmest months and roughly -7ºC in the coldest. Bear this in mind when deciding what to pack and planning time outdoors.

Highs: up to 29ºC
Lows: down to -9ºC
Hottest month: July
Coldest month: January
Driest month: January
Wettest month: August

Tips for cheaper flights from Boston to Chicago

A few ways to bring down the cost of your flight from Boston to Chicago:

Flexible dates: check fares across two or three departure days. Going a day earlier or later can make a real difference to what you pay.
Baggage allowance: see what's included in each fare before booking, so you're not stung by unexpected charges at the airport.
Airports on your route: double-check which airports you'll fly from and into, particularly if the city has more than one. It makes it easier to plan transfers and work out the full cost of getting around.

After a bigger saving? Book a Flight + Hotel package to combine the two in a single booking and unlock exclusive discounts on your stay in Chicago. Adding car hire to the same booking can save you money too.

Frequently asked questions about flights from Boston to Chicago

On average, how much is the price of a flight from Boston to Chicago?

When you fly from Boston to Chicago the average price is £115. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.

How can I find cheap flights from Boston to Chicago at Opodo?

The cheapest price for a flight from Boston to Chicago is 95 £. At Opodo we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.

When is the best time to book a flight from Boston to Chicago?

The most popular months to book a flight from Boston to Chicago are May, April and January, based on the searches of our customers.

When is the best time to travel from Boston to Chicago?

The best time of the year to go to Chicago when flying from Boston depends on several preference factors like climate, seasonality and, of course, price. When it comes to popularity, October is the top 1º month to fly to Chicago from Boston in terms of searches from our customer, followed by June and September. If you prefer to avoid high peaks of turism, however, and escape a crowded period, January, April and February are the months with less volume of searchs for the route Boston - Chicago.

How long does the flight take to go from Boston to Chicago?

The total flight time between Boston and Chicago is of around 3 h and 17 m on average, considering an average distance of 854.07 mi, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).

How is the weather in Chicago compared to Boston?

While in Boston temperatures can reach an average of 22º ºC in summer, Chicago can experience temperatures up to 22º ºC during the hot season. In winter, however, the weather shows around -3º ºC in Chicago, compared to the 0º ºC average in Boston.

Which airports have flights between Boston and Chicago?

The main airport route flying between Boston and Chicago is: Logan International Airport (BOS) to O'hare International Airport(ORD). This route is covered by the following airline(s):

Which are the airlines with flights from Boston to Chicago?

Airlines with direct flights departing from Boston to Chicago are:

American Airlines.

American Airlines

Frontier Airlines
SUN COUNTRY

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