United's Economy Plus offers extra legroom, ideal for comfort on short flights.
United's MileagePlus allows pooling miles, useful for family travel.

Most accurate provider | eDreams 3 stars  | 
|---|---|
Most trusted provider | eDreams 3 stars  | 
Round-trip from | $117 (JetBlue)  | 
One-way from | $59 (United Airlines)  | 
Popular in | April | 
Cheapest in | September | 
Average price | $230 | 
Good round-trip deal | $158 or less | 
Good one-way deal | $88 or less | 
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 12/10
1:30 pm-4:45 pm
Nonstop2h 15m
Boston Logan Intl
Sat 12/13
5:20 am-7:05 am
Nonstop2h 45m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 12/4
7:10 am-10:36 am
Nonstop2h 26m
Boston Logan Intl
Sun 12/7
7:52 pm-9:47 pm
Nonstop2h 55m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 12/24
6:15 pm-9:35 pm
Nonstop2h 20m
Boston Logan Intl
Sun 12/28
5:15 am-7:00 am
Nonstop2h 45m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 11/8
1:55 pm-5:15 pm
Nonstop2h 20m
Boston Logan Intl
Thu 11/13
9:40 am-11:40 am
Nonstop3h 00m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 11/24
7:10 am-10:35 am
Nonstop2h 25m
Boston Logan Intl
Thu 12/4
4:05 pm-6:02 pm
Nonstop2h 57m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 11/13
7:15 am-10:34 am
Nonstop2h 19m
Boston Logan Intl
Sat 11/15
6:23 pm-8:23 pm
Nonstop3h 00m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 12/4
6:15 pm-9:35 pm
Nonstop2h 20m
Boston Logan Intl
Sun 12/7
6:50 pm-11:30 pm
1 stop5h 40m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 11/15
9:50 am-1:10 pm
Nonstop2h 20m
Boston Logan Intl
Sat 11/15
4:45 pm-6:30 pm
Nonstop2h 45m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 12/23
7:50 pm-11:05 pm
Nonstop2h 15m
Boston Logan Intl
Sat 12/27
5:20 am-7:05 am
Nonstop2h 45m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 12/25
6:15 pm-9:35 pm
Nonstop2h 20m
Boston Logan Intl
Sat 1/3
6:55 pm-11:20 pm
1 stop5h 25m
| Provider | Price Accuracy | Trust Score* | 
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | 
The price you pay for your flight from Chicago to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 89 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, November is the cheapest month in which you can book a flight from Chicago to Boston (average of $71). Flying from Chicago to Boston in February is currently the most expensive (average of $137). 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 typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 43% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to BOS are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 on average).
Food
Entertainment
Comfort
Crew
Boarding
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Food
Entertainment
Comfort
Crew
Boarding
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Food
Entertainment
Comfort
Crew
Boarding
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Food
Entertainment
Comfort
Crew
Boarding
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Food
Entertainment
Comfort
Crew
Boarding
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Food
Entertainment
Comfort
Crew
Boarding
Overall
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$68 | Average$151 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$76 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$102 | Average$230 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$104 | Average$115 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$231 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$118 | Average$272 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$250 | FlexibilityNo cancel fee | On-time63% |