
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Delta) |
One-way from | $68 (Cheapflightsfares) |
Popular in | February |
Cheapest in | September |
Average price | $254 |
Good round-trip deal | $177 or less |
Good one-way deal | $88 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/1
7:59 pm-11:27 pm
Nonstop2h 28m
Boston Logan Intl
Sun 5/3
6:00 am-8:09 am
Nonstop3h 09m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/6
1:55 pm-5:22 pm
Nonstop2h 27m
Boston Logan Intl
Fri 5/8
7:26 pm-11:37 pm
1 stop5h 11m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 3/12
6:00 am-11:10 am
1 stop4h 10m
Boston Logan Intl
Sun 3/15
7:16 am-9:22 am
Nonstop3h 06m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/13
7:15 pm-10:49 pm
Nonstop2h 34m
Boston Logan Intl
Sun 5/17
7:35 am-9:27 am
Nonstop2h 52m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 3/28
3:40 pm-10:41 pm
1 stop6h 01m
Boston Logan Intl
Mon 3/30
6:00 am-7:59 am
Nonstop2h 59m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/23
4:30 pm-8:03 pm
Nonstop2h 33m
Boston Logan Intl
Mon 5/25
8:40 pm-10:35 pm
Nonstop2h 55m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 3/7
7:05 am-10:37 am
Nonstop2h 32m
Boston Logan Intl
Tue 3/10
11:30 am-1:27 pm
Nonstop2h 57m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 4/11
1:55 pm-10:05 pm
1 stop7h 10m
Boston Logan Intl
Sun 4/12
8:15 am-12:50 pm
1 stop5h 35m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 4/3
4:20 pm-11:59 pm
1 stop6h 39m
Boston Logan Intl
Sun 4/5
5:45 am-9:38 am
1 stop4h 53m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/1
1:55 pm-5:31 pm
Nonstop2h 36m
Boston Logan Intl
Sun 8/16
8:00 am-9:56 am
Nonstop2h 56m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 43 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $91). Flying from Chicago O'Hare Intl Airport to Boston in January is currently the most expensive (average of $117). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
About 23% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 153 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, JetBlue have had the lowest number of delays on this route, with just 19% of flights being delayed.
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$158 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$91 | Average$218 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$231 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$252 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |