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Prepay for checked bags on United to save money. Avoid fees by using MileagePlus Premier benefits.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $117 (JetBlue) |
One-way from | $59 (JetBlue) |
Popular in | April |
Cheapest in | September |
Average price | $289 |
Good round-trip deal | $211 or less |
Good one-way deal | $106 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/8
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Mon 5/12
6:25 pm-9:57 pm
Nonstop2h 32m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/12
5:00 am-6:54 am
Nonstop2h 54m
Chicago O'Hare Intl
Thu 6/19
8:40 pm-12:20 am
Nonstop2h 40m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 9/3
11:56 am-8:40 pm
1 stop9h 44m
Chicago O'Hare Intl
Tue 9/9
7:15 am-3:35 pm
1 stop7h 20m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/11
5:45 am-11:50 am
1 stop7h 05m
Chicago O'Hare Intl
Wed 5/14
1:50 pm-7:10 pm
1 stop4h 20m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/12
7:00 am-8:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Tue 8/12
2:10 pm-5:52 pm
Nonstop2h 42m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/29
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Tue 6/3
7:31 pm-11:00 pm
Nonstop2h 29m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/28
3:49 pm-11:04 pm
1 stop8h 15m
Chicago O'Hare Intl
Sun 6/1
5:14 pm-8:35 am
1 stop14h 21m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/9
12:52 pm-11:11 pm
1 stop11h 19m
Chicago O'Hare Intl
Sun 5/11
4:15 pm-1:05 am
1 stop7h 50m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/5
4:20 pm-6:21 pm
Nonstop3h 01m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/30
6:59 pm-11:37 pm
1 stop5h 38m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy2 stars | Trust Score*3 stars | |
Price Accuracy- | Trust Score*3 stars | |
Price Accuracy- | 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 57 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, August is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $245). Flying from Boston to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 32% on the cost of your flight, compared to a flight in the afternoon.
Travelers seeking maximum savings on their Boston to Chicago O'Hare Intl Airport flight should consider departing on Saturday 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.
The most flights from BOS to ORD are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).
In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Crew
Comfort
Overall
Boarding
Food
Entertainment
Reviews
James,Apr 2025
LAX - SFO
Crew
Comfort
Overall
Boarding
Food
Entertainment
Reviews
James,Apr 2025
LAX - SFO
Crew
Comfort
Overall
Boarding
Food
Entertainment
Reviews
James,Apr 2025
LAX - SFO
Crew
Comfort
Overall
Boarding
Food
Entertainment
Reviews
James,Apr 2025
LAX - SFO
Crew
Comfort
Overall
Boarding
Food
Entertainment
Reviews
James,Apr 2025
LAX - SFO
Crew
Comfort
Overall
Boarding
Food
Entertainment
Reviews
James,Apr 2025
LAX - SFO
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$39 | Average$105 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$83 | Average$220 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$93 | Average$244 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$100 | Average$134 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$139 | Average$261 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$147 | Average$290 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$182 | Average$378 | FlexibilityNo cancel fee | On-time63% |