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 | $153 (United Airlines) |
One-way from | $79 (Cheapflightsfares) |
Popular in | April |
Cheapest in | September |
Average price | $270 |
Good round-trip deal | $197 or less |
Good one-way deal | $108 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 4/8
4:40 pm-12:47 am
1 stop7h 07m
Boston Logan Intl
Tue 4/15
6:00 am-4:08 pm
1 stop11h 08m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 3/18
4:00 pm-7:20 pm
Nonstop2h 20m
Boston Logan Intl
Mon 3/24
4:17 pm-10:00 pm
1 stop6h 43m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 4/4
7:21 pm-9:29 am
1 stop13h 08m
Boston Logan Intl
Tue 4/8
11:14 am-11:59 pm
1 stop13h 45m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/8
7:21 pm-10:27 am
1 stop14h 06m
Boston Logan Intl
Thu 4/10
6:00 am-8:49 am
1 stop27h 49m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 3/29
10:05 am-1:24 pm
Nonstop2h 19m
Boston Logan Intl
Tue 4/1
3:20 pm-5:19 pm
Nonstop2h 59m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 3/31
8:36 pm-12:06 am
Nonstop2h 30m
Boston Logan Intl
Sat 4/5
8:00 am-10:07 am
Nonstop3h 07m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/1
8:50 am-12:18 pm
Nonstop2h 28m
Boston Logan Intl
Sun 5/4
6:00 am-8:05 am
Nonstop3h 05m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 3/17
7:35 am-10:50 am
Nonstop2h 15m
Boston Logan Intl
Wed 3/19
5:45 am-7:35 am
Nonstop2h 50m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 3/18
9:25 am-12:34 am
1 stop14h 09m
Boston Logan Intl
Sun 3/23
6:00 am-7:44 am
1 stop26h 44m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/23
1:50 pm-7:10 pm
1 stop4h 20m
Boston Logan Intl
Sun 4/27
6:40 am-2:05 pm
1 stop8h 25m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy1 star | Trust Score*3 stars |
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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 79 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 July is currently the most expensive (average of $311). 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 32% 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.
If weather is an important factor for your trip to Boston, 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 30.2 F).
Food
Comfort
Overall
Entertainment
Boarding
Crew
Reviews
Ila,Mar 2025
HOU - DAL
Food
Comfort
Overall
Entertainment
Boarding
Crew
Reviews
Ila,Mar 2025
HOU - DAL
Food
Comfort
Overall
Entertainment
Boarding
Crew
Reviews
Ila,Mar 2025
HOU - DAL
Food
Comfort
Overall
Entertainment
Boarding
Crew
Reviews
Ila,Mar 2025
HOU - DAL
Food
Comfort
Overall
Entertainment
Boarding
Crew
Reviews
Ila,Mar 2025
HOU - DAL
Food
Comfort
Overall
Entertainment
Boarding
Crew
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$38 | Average$96 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$63 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$85 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$86 | Average$113 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$141 | Average$252 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$157 | Average$298 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$157 | Average$284 | FlexibilityNo cancel fee | On-time63% |