Statistics on Chicago-Boston flights: what is the right price and when to buy your plane ticket?
Best time to go: what is the RIGHT price for a round-trip flight to Boston (from: Chicago)
The average price to go to Boston from Chicago airport is $ 243 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 177 (in september) and $ 306 (in march), which is a saving of $ 67 or a surplus of $ 64 (compared to the average price) depending on the period you leave.
The analysis of all the prices reveals that the most frequent price is between $166 to $221 and that it is generally more economical to leave on a wednesday and return on a wednesday on a direct flight.
Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Boston before booking your flight.
If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Chicago-Boston plane ticket.
How are these data calculated?
We have studied a sample of 60000 airfare prices from previous years for flights to Boston from Chicago and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.
Average price depending on the departure month
Data analysis:
By leaving in september, the price of the plane ticket will statistically be the cheapest ($ 177, saving $ 67 compared to the average price over the year which is $ 243). Conversely, march will be the most expensive ($ 306).
Flight Chicago-Boston: when is the best time to go for the best price?
| Month | Good price* | Average price | Our opinion |
|---|---|---|---|
| January | $ 151 | $ 211 | good price |
| February | $ 155 | $ 212 | good price |
| March | $ 194 | $ 306 the most expensive | very high price |
| April | $ 222 | $ 291 | high price |
| May | $ 197 | $ 236 | fair price |
| June | $ 203 | $ 262 | fair price |
| July | $ 201 | $ 256 | fair price |
| August | $ 161 | $ 210 | good price |
| September | $ 152 | $ 177 the cheapest | very good price |
| October | $ 160 | $ 217 | fair price |
| November | $ 180 | $ 269 | high price |
| December | $ 188 | $ 255 | fair price |
*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!
Price breakdown to travel from Chicago to Boston
Data analysis:
The prices for flights from Chicago to Boston range from $55 to $716. 6% of tickets were purchased at the minimum price (from $56 to $111), 2% at the maximum price (from $661 to $716). The majority of plane tickets were purchased in the range of $166 to $221 (30% of tickets).
Cheapest airlines for the Chicago->Boston flight
There are 8 companies that serve Chicago from Boston airport: jetBlue, United, Spirit Airlines, Frontier Airlines, American Airlines, Delta, Air New Zealand and Alaska Airlines.
Data analysis:
Of the 60000 flights analyzed in previous years, jetBlue was the airline that offered the best fare most often in the flight ticket search results (26% of the time) on the Chicago->Boston route.
Direct flight or flight with layover?
Data analysis:
To get the best price for the Chicago-Boston flight, you should take a direct flight (saving an average of $ 56 compared to a flight with one or more layovers).
Which day of the week to leave?
Data analysis:
Statistically, Chicago-Boston flights departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday as your departure date, you can save an average of $27. On the other hand, departing on a sunday may cost you an additional $72.
Which day of the week to come back?
Data analysis:
Statistically, return flights from Boston to Chicago departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday for your return date, you will save an average of $34. Conversely, departing from Boston on a friday may cost you an additional $47.
Top prices Chicago-Boston
| Round trip | Dates | Price | |
|---|---|---|---|
| Chicago → Boston | 20-04 to 30-04-2025 | $ 103 | direct flight with jetBlue |
| Chicago → Boston | 08-05 to 13-05-2025 | $ 100 | direct flight with United |
| Chicago → Boston | 04-06 to 08-06-2025 | $ 115 | direct flight with jetBlue |
| Chicago → Boston | 06-06 to 10-06-2025 | $ 114 | direct flight with jetBlue |
| Chicago → Boston | 18-07 to 22-07-2025 | $ 98 | direct flight with Southwest Airlines |
| Chicago → Boston | 04-09 to 08-09-2025 | $ 114 | direct flight with jetBlue |
| Chicago → Boston | 08-09 to 16-09-2025 | $ 115 | direct flight with jetBlue |
| Chicago → Boston | 13-10 to 18-10-2025 | $ 116 | direct flight with United |
| Chicago → Boston | 01-11 to 07-11-2025 | $ 100 | direct flight with United |
| Chicago → Boston | 06-11 to 11-11-2025 | $ 114 | direct flight with Spirit Airlines |
When to book your flight Chicago - Boston to get the cheapest price?
Statistically, you will make the biggest savings by buying your plane ticket between 1 to 2 months in advance. However, you may end up paying a high price if you book between 10 to 11 months in advance.
Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Chicago-Boston flight, it is recommended to book your ticket on a friday.
How far in advance should I buy my flight?
Data analysis:
To get the cheapest flight ticket from Chicago to Boston, it is recommended to buy it 1 to 2 months before departure (it is then on average 199 $, which is a saving of 44 $ compared to the overall average price). On the other hand, if you buy your ticket 10 to 11 months in advance, you will pay the full price (110 $ more than the average price).
Depending on the departure month
The best time to buy your Chicago to Boston flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.
| Departure on... | How far in advance should I book? |
|---|---|
| January | Best time: 1 to 2 months before departure (average price: 173 $) Other interesting period(s): 0 to 1 month ($ 188), 2 to 3 months ($ 175) |
| February | Best time: 1 to 2 months before departure (average price: 183 $) Other interesting period(s): 0 to 1 month ($ 211), 2 to 3 months ($ 193), 3 to 4 months ($ 203) |
| March | Best time: 1 to 2 months before departure (average price: 243 $) Other interesting period(s): 0 to 1 month ($ 261), 2 to 3 months ($ 271), 3 to 4 months ($ 304) |
| April | Best time: 1 to 2 months before departure (average price: 239 $) Other interesting period(s): 0 to 1 month ($ 283), 2 to 3 months ($ 268), 3 to 4 months ($ 288) |
| May | Best time: 1 to 2 months before departure (average price: 202 $) Other interesting period(s): 2 to 3 months ($ 219), 3 to 4 months ($ 228), 7 to 8 months ($ 234) |
| June | Best time: 1 to 2 months before departure (average price: 227 $) Other interesting period(s): 0 to 1 month ($ 235), 2 to 3 months ($ 241) |
| July | Best time: 1 to 2 months before departure (average price: 213 $) Other interesting period(s): 0 to 1 month ($ 224), 2 to 3 months ($ 240) |
| August | Best time: 1 to 2 months before departure (average price: 191 $) Other interesting period(s): 0 to 1 month ($ 197), 2 to 3 months ($ 194), 3 to 4 months ($ 206) |
| September | Best time: 1 to 2 months before departure (average price: 157 $) Other interesting period(s): 2 to 3 months ($ 169), 3 to 4 months ($ 160), 4 to 5 months ($ 171) |
| October | Best time: 2 to 3 months before departure (average price: 180 $) Other interesting period(s): 0 to 1 month ($ 215), 1 to 2 months ($ 181), 5 to 6 months ($ 205) |
| November | Best time: 1 to 2 months before departure (average price: 204 $) Other interesting period(s): 0 to 1 month ($ 248), 2 to 3 months ($ 217), 3 to 4 months ($ 254), 7 to 8 months ($ 237) |
| December | Best time: 1 to 2 months before departure (average price: 200 $) Other interesting period(s): 0 to 1 month ($ 234), 2 to 3 months ($ 241) |
What day of the week should I book my flight ticket?
Data analysis:
Statistically, friday is the day when plane tickets for Chicago->Boston are the cheapest. So, by buying your plane ticket on a friday, you will save $4. Conversely, by buying it on a sunday, you may end up paying $5 more.
Chicago to Boston: flight price when booking today
Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.
| Month | Current price | Our opinion | |
|---|---|---|---|
| April 2025 | $ 203 $103 to $507 | very good price | Find a flight |
| May 2025 | $ 196 $98 to $402 | very good price | Find a flight |
| June 2025 | $ 161 $108 to $305 | very good price | Find a flight |
| July 2025 | $ 156 $98 to $255 | very good price | Find a flight |
| August 2025 | $ 145 $100 to $200 | very good price | Find a flight |
| September 2025 | $ 124 $114 to $202 | very good price | Find a flight |
| October 2025 | $ 157 $116 to $303 | very good price | Find a flight |
| November 2025 | $ 314 $100 to $545 | high price | Find a flight |
| February 2026 | $ 186 $186 to $186 | very good price | Find a flight |
Data analysis:
Compared to the average price, april, may, june, july, august, september, october and february are cheaper to travel to Boston. So it may be interesting to book now to leave during these months!