
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
So 7/26
5:01 am-8:50 am
1 stop4h 49m
Chicago O'Hare Intl
Do 8/27
5:27 pm-11:59 pm
1 stop5h 32m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mo 8/31
4:16 pm-6:20 pm
Nonstop3h 04m
Chicago O'Hare Intl
Fr 9/4
7:30 pm-11:00 pm
Nonstop2h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mi 7/22
4:31 pm-9:58 pm
1 stop6h 27m
Chicago O'Hare Intl
Fr 8/28
10:56 am-2:23 pm
Nonstop2h 27m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sa 7/25
5:01 am-8:51 am
1 stop4h 50m
Chicago O'Hare Intl
Fr 8/28
5:27 pm-11:59 pm
1 stop5h 32m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Do 7/2
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
Sa 7/11
6:59 am-10:30 am
Nonstop2h 31m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Do 8/13
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Mo 8/17
7:59 pm-11:34 pm
Nonstop2h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mo 8/3
5:10 pm-9:58 pm
1 stop5h 48m
Chicago O'Hare Intl
Fr 8/14
8:20 pm-11:51 pm
Nonstop2h 31m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Do 7/23
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Di 7/28
6:00 am-11:16 am
1 stop4h 16m
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sa 9/5
1:31 pm-4:45 pm
Nonstop3h 14m
Orlando
Di 9/8
9:34 pm-12:42 am
Nonstop3h 08m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fr 6/26
4:15 pm-6:20 pm
Nonstop3h 05m
Chicago O'Hare Intl
Sa 7/18
4:30 pm-8:11 pm
Nonstop2h 41m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star |
Currently, October is the cheapest month in which you can book a flight from Boston (average of $328). Flying from Boston in December will prove the most costly (average of $532). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
For flights departing from Boston check dates and pricing for the following: Delta, Alaska Airlines, JetBlue, American Airlines, Hawaiian Airlines. These airlines depart to the following popular destinations: Seattle.
Some of the most frequent flights departing from Boston everyday are: New York (1,215 flights per day), Chicago (713 flights per day), and Washington, D.C. (563 flights per day).
The cheapest city to fly to from Boston is Presque Isle, with prices starting at $43. Explore other affordable destinations below.
To ensure you get the cheapest price possible for a flight from Boston, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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Anonymous,Jun 2026
RDU - SEA
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Food
Overall
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RDU - SEA
Food
Overall
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RDU - SEA
Food
Overall
Comfort
Crew
Boarding
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Anonymous,Jun 2026
RDU - SEA
Food
Overall
Comfort
Crew
Boarding
Entertainment
Reviews
Anonymous,Jun 2026
RDU - SEA