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 | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Delta) |
One-way from | $67 (CheapOair) |
Popular in | April |
Cheapest in | September |
Average price | $244 |
Good round-trip deal | $167 or less |
Good one-way deal | $102 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 11/7
2:55 pm-11:15 pm
1 stop7h 20m
Boston Logan Intl
Mon 11/10
6:55 pm-8:45 pm
Nonstop2h 50m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 10/31
4:55 pm-8:10 pm
Nonstop2h 15m
Boston Logan Intl
Tue 11/4
12:20 pm-5:50 pm
1 stop6h 30m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 11/9
9:20 am-12:44 pm
Nonstop2h 24m
Boston Logan Intl
Sun 11/16
7:30 am-9:30 am
Nonstop3h 00m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 10/28
10:25 am-1:55 pm
Nonstop2h 30m
Boston Logan Intl
Tue 10/28
7:30 pm-9:19 pm
Nonstop2h 49m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 11/5
12:55 pm-9:05 pm
1 stop7h 10m
Boston Logan Intl
Sat 11/8
9:20 am-6:30 pm
1 stop10h 10m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 10/25
10:00 am-6:50 pm
2 stops7h 50m
Boston Logan Intl
Tue 10/28
5:40 pm-10:05 pm
1 stop5h 25m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 11/5
12:55 pm-9:05 pm
1 stop7h 10m
Boston Logan Intl
Sun 11/9
6:50 am-3:40 pm
1 stop9h 50m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 11/6
9:35 am-5:15 pm
1 stop6h 40m
Boston Logan Intl
Sun 11/9
6:50 am-3:40 pm
1 stop9h 50m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/23
9:20 pm-12:50 am
Nonstop2h 30m
Boston Logan Intl
Wed 11/5
6:00 am-8:00 am
Nonstop3h 00m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 10/24
7:13 pm-10:46 pm
Nonstop2h 33m
Boston Logan Intl
Tue 10/28
3:55 pm-5:55 pm
Nonstop3h 00m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy2 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy2 stars | Trust Score*2 stars | |
Price Accuracy2 stars | Trust Score*1 star | |
Price Accuracy1 star | Trust Score*3 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 $138). 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 41% 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 Sunday (81 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (50 on average).
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$58 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$79 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$97 | Average$228 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$104 | Average$115 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$118 | Average$231 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$125 | Average$275 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$137 | Average$253 | FlexibilityNo cancel fee | On-time63% |