
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $150 (Delta) |
One-way from | $76 (Frontier) |
Popular in | April |
Cheapest in | January |
Average price | $285 |
Good round-trip deal | $234 or less |
Good one-way deal | $133 or less |
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/9
8:45 pm-10:42 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sat 6/13
4:30 pm-8:11 pm
Nonstop2h 41m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/30
9:00 am-1:21 pm
1 stop5h 21m
Chicago O'Hare Intl
Mon 6/1
5:19 pm-11:29 pm
1 stop5h 10m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/28
5:51 am-11:47 am
1 stop6h 56m
Chicago O'Hare Intl
Tue 6/2
7:05 am-2:15 pm
1 stop6h 10m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
8:10 am-10:06 am
Nonstop2h 56m
Chicago O'Hare Intl
Tue 7/7
8:20 pm-11:51 pm
Nonstop2h 31m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/10
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Wed 5/27
9:36 am-4:28 pm
1 stop5h 52m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/9
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Thu 6/11
9:26 pm-12:59 am
Nonstop2h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/9
7:27 pm-11:26 pm
1 stop4h 59m
Chicago O'Hare Intl
Sat 6/13
3:55 pm-7:30 pm
Nonstop2h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/10
8:10 am-10:08 am
Nonstop2h 58m
Chicago O'Hare Intl
Sun 9/13
6:00 am-9:23 am
Nonstop2h 23m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/21
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 5/25
6:15 am-9:39 am
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/27
8:10 pm-10:06 pm
Nonstop2h 56m
Chicago O'Hare Intl
Sun 8/30
7:00 am-10:28 am
Nonstop2h 28m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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*3 stars |
To ensure you get the cheapest price possible for a flight from Boston to Chicago O'Hare Intl Airport, you should look to book at least 41 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.
Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $197). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of $285). 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.
It’s optimal to fly from Boston to Chicago O'Hare Intl Airport in the evening. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight at noon.
Travelers seeking maximum savings on their Boston to Chicago O'Hare Intl Airport 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 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 172 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening 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, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Jim,Nov 2025
AVL - ATL
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Jim,Nov 2025
AVL - ATL
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Jim,Nov 2025
AVL - ATL
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Jim,Nov 2025
AVL - ATL
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Jim,Nov 2025
AVL - ATL
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Jim,Nov 2025
AVL - ATL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$32 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$258 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$263 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$130 | Average$258 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$156 | Average$156 | FlexibilityNo cancel fee | On-time63% |