United's Economy Plus offers extra legroom, ideal for comfort on short flights.
United's MileagePlus allows pooling miles, useful for family travel.
Round-trip from | $132 (Priceline) |
---|---|
One-way from | $68 (FlightHub) |
Popular in | April |
Cheapest in | August |
Average price | $225 |
Good round-trip deal | $137 or less |
Good one-way deal | $68 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/9
11:45 am-11:55 pm
1 stop11h 10m
Boston Logan Intl
Sat 9/13
8:38 am-4:49 pm
1 stop9h 11m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/2
12:20 pm-12:39 am
1 stop11h 19m
Boston Logan Intl
Thu 8/7
6:00 am-1:56 pm
1 stop8h 56m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/11
8:40 am-12:04 pm
Nonstop2h 24m
Boston Logan Intl
Wed 7/16
6:00 am-7:55 am
Nonstop2h 55m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 8/16
3:55 pm-7:15 pm
Nonstop2h 20m
Boston Logan Intl
Mon 8/18
5:15 am-6:45 am
Nonstop2h 30m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/29
5:05 am-7:34 pm
1 stop13h 29m
Boston Logan Intl
Tue 7/29
8:39 pm-8:55 am
1 stop13h 16m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 9/19
6:21 am-8:11 am
1 stop24h 50m
Boston Logan Intl
Mon 9/22
10:53 am-3:58 pm
1 stop6h 05m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/15
11:05 am-2:42 pm
Nonstop2h 37m
Boston Logan Intl
Tue 7/15
7:04 pm-11:41 pm
1 stop5h 37m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/22
2:55 pm-10:35 pm
1 stop6h 40m
Boston Logan Intl
Tue 8/26
5:40 am-11:50 am
1 stop7h 10m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/29
8:25 pm-11:59 pm
Nonstop2h 34m
Boston Logan Intl
Tue 9/2
8:35 am-10:30 am
Nonstop2h 55m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/30
2:10 pm-5:54 pm
Nonstop2h 44m
Boston Logan Intl
Sun 8/31
7:20 am-9:15 am
Nonstop2h 55m
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 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $218). Flying from Chicago to Boston in June is currently the most expensive (average of $306). 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 26% on the flight price compared to flying in the afternoon, which is usually more expensive.
Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Wednesday 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 CHI to BOS are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$36 | Average$95 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$78 | Average$194 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$90 | Average$222 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$100 | Average$115 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$125 | Average$232 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$130 | Average$289 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$153 | Average$276 | FlexibilityNo cancel fee | On-time63% |