
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $70 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $320 |
Good round-trip deal | $277 or less |
Good one-way deal | $148 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 4/13
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Wed 4/15
6:00 am-7:59 am
Nonstop2h 59m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Wed 6/3
8:40 pm-10:35 pm
Nonstop2h 55m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 5/6
3:15 pm-6:35 pm
Nonstop2h 20m
Boston Logan Intl
Wed 5/13
7:20 am-9:05 am
Nonstop2h 45m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Tue 8/25
11:00 am-12:52 pm
Nonstop2h 52m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 5/7
9:25 am-12:40 pm
Nonstop2h 15m
Boston Logan Intl
Sat 5/9
3:30 pm-5:15 pm
Nonstop2h 45m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 6/3
12:50 pm-7:40 pm
2 stops5h 50m
Boston Logan Intl
Tue 6/9
5:50 am-10:45 am
1 stop5h 55m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 6/4
9:26 pm-12:59 am
Nonstop2h 33m
Boston Logan Intl
Sun 6/7
6:00 am-7:58 am
Nonstop2h 58m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 4/6
7:35 pm-11:02 pm
Nonstop2h 27m
Boston Logan Intl
Thu 4/9
7:15 am-9:25 am
Nonstop3h 10m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 6/5
4:00 pm-7:20 pm
Nonstop2h 20m
Boston Logan Intl
Mon 6/8
8:00 pm-12:15 am
1 stop5h 15m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 5/28
2:10 pm-11:10 pm
1 stop8h 00m
Boston Logan Intl
Sun 5/31
6:10 am-7:55 am
Nonstop2h 45m
Currently, October is the cheapest month in which you can book a flight from Chicago to Maine (average of $206). Flying from Chicago to Maine in November is currently the most expensive (average of $276). 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.
When flying from Chicago to Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 19% versus a flight in the morning.
Travelers seeking maximum savings on their Chicago to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to USME are scheduled on a Thursday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
Entertainment
Food
Boarding
Overall
Crew
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Boarding
Overall
Crew
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Boarding
Overall
Crew
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Boarding
Overall
Crew
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Boarding
Overall
Crew
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$371 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$460 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$263 | Average$399 | FlexibilityNo cancel fee | On-timeN/A |