$66+ Cheap flights from Chicago (CHI) to Maine
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
févr. 28 — mars 71
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maine
Cheapest flights from Chicago to MaineExplore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janvier 29, 2026.
Explore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janvier 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/177:00 am
ORD
- BOS
1 stop9h 15m
Multiple Airlines
ven. 2/276:00 am
BOS
- ORD
1 stop29h 51m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$131
This Priceline deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/256:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
sam. 2/287:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/247:23 pm
ORD
- BOS
1 stop20h 22m
Multiple Airlines
mar. 3/36:00 am
BOS
- ORD
1 stop11h 52m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/55:01 pm
MDW
- BOS
1 stop7h 12m
Frontier
lun. 2/96:00 am
BOS
- MDW
1 stop6h 45m
Frontier
Deal found 1/26![Frontier logo]()
$133
This Cheapflightsfares deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 1/317:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
lun. 2/23:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 1/28![JetBlue logo]()
$134
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/1811:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
sam. 2/214:25 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 1/28![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 1/305:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
dim. 2/15:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 1/27![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
mar. 3/33:50 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 1/27![Delta logo]()
$136
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
mer. 2/257:45 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 1/27![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/256:40 pm
ORD
- BOS
Nonstop2h 29m
Delta
sam. 2/289:05 am
BOS
- ORD
1 stop8h 49m
Delta
Deal found 1/28![Delta logo]()
$138
This Kissandfly.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 1/307:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
dim. 2/16:10 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 1/27![JetBlue logo]()
$139
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 2/2811:45 am
MDW
- BOS
1 stop6h 30m
Delta
mar. 3/36:55 am
BOS
- MDW
1 stop6h 04m
Delta
Deal found 1/28![Delta logo]()
$139
Find flight deals from Chicago to Maine
Keep the following information in mind while searching for Chicago to Maine flight deals. Data was last updated janvier 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (Kiwi.com) |
One-way from | $66 (Kiwi.com) |
Popular in | April |
Cheapest in | March |
Average price | $398 |
Good round-trip deal | $234 or less |
Good one-way deal | $195 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maine that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated janvier 29, 2026.
Use the filters below to find and compare flights from Chicago to Maine that are best for you.
Fly from
Chicago
Fly to
Maine
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
mer. 4/29
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
sam. 5/2
7:35 pm-9:36 pm
Nonstop3h 01m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
sam. 2/28
7:05 am-10:37 am
Nonstop2h 32m
Boston Logan Intl
mar. 3/3
3:50 pm-5:53 pm
Nonstop3h 03m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
mer. 6/3
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
sam. 6/6
6:00 am-7:58 am
Nonstop2h 58m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
mer. 5/27
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
sam. 5/30
7:00 am-8:58 am
Nonstop2h 58m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
mar. 4/21
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
mer. 5/13
6:52 am-8:51 am
Nonstop2h 59m
$135
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
sam. 2/28
11:45 am-7:15 pm
1 stop6h 30m
Boston Logan Intl
sam. 3/7
5:29 am-8:54 am
1 stop4h 25m
$139
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
mer. 2/25
10:00 am-1:20 pm
Nonstop2h 20m
Boston Logan Intl
mer. 3/4
7:07 am-12:04 pm
1 stop5h 57m
$151
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
mer. 4/22
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
mar. 4/28
7:35 pm-9:36 pm
Nonstop3h 01m
$151
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
mer. 2/25
10:49 am-5:32 pm
1 stop5h 43m
Boston Logan Intl
sam. 2/28
5:29 am-8:54 am
1 stop4h 25m
$152
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
sam. 2/28
1:02 pm-7:08 pm
1 stop5h 06m
Boston Logan Intl
lun. 3/2
6:28 pm-8:30 pm
Nonstop3h 02m
$153
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Maine
Have a flexible travel schedule? Discover the best time to fly to Maine from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maine
What is the cheapest month to book a flight from Chicago to Maine?
Currently, October is the cheapest month in which you can book a flight from Chicago to Maine (average of $205). 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.
What is the cheapest time of day to fly from CHI to ME?
Find hourly flight availability from Chicago to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated janvier 29, 2026.
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 21% versus a flight in the evening.
What is the cheapest day to fly from Chicago to Maine?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Maine. Price data was last updated on January 24, 2026.
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.
Weekly flight availability from Chicago to Maine
Explore weekly flight availability from Chicago to Maine. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated janvier 29, 2026.
The most flights from CHI to USME are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chicago to Maine?
Reviews of airlines servicing Maine
Get insights into the airlines that provide service to Maine. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maine. Reviews last updated janvier 29, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Maine by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maine. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Chicago to Maine
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Chicago to Maine
Discover the top 4 airlines that operate flights from Chicago to Maine. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated janvier 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$210 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$460 | FlexibilityNo cancel fee | On-time63% |