$63+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Jan 17 — Jan 241
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Maine with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 December 18, 2025.
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 December 18, 2025.
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/14:15 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/17![United Airlines logo]()
$127
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Mon 1/56:23 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 12/17![United Airlines logo]()
$132
This JetBlue deal was found by Cheapflights users on 12/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:15 pmORD - BOS
Nonstop2h 29mJetBlue
Sun 12/284:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17![JetBlue logo]()
$137
This JetBlue deal was found by Cheapflights users on 12/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:41 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 12/304:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17![JetBlue logo]()
$147
This Southwest deal was found by Cheapflights users on 12/17. 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.
Wed 12/248:25 amMDW - BOS
1 stop7h 55mSouthwest
Thu 1/15:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/17![Southwest logo]()
$153
This Priceline deal was found by Cheapflights users on 12/17. 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.
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Thu 1/14:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17![JetBlue logo]()
$157
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Sun 12/219:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/86:21 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/15![United Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:21 pmORD - BOS
1 stop4h 33mUnited Airlines
Thu 1/16:29 pmBOS - ORD
Nonstop3h 06mUnited Airlines
Deal found 12/17![United Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:21 pmORD - BOS
1 stop4h 33mUnited Airlines
Mon 1/56:23 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 12/17![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 12/16. 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.
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Tue 1/137:55 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 12/16![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Wed 12/3112:20 pmBOS - ORD
Nonstop3h 03mUnited Airlines
Deal found 12/16![United Airlines logo]()
$179
This JetBlue deal was found by Cheapflights users on 12/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:15 pmORD - BOS
Nonstop2h 29mJetBlue
Wed 12/315:05 pmBOS - ORD
1 stop5h 59mJetBlue
Deal found 12/17![JetBlue logo]()
$181
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 December 18, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $124 (Kiwi.com) |
One-way from | $63 (Super.com) |
Popular in | April |
Cheapest in | September |
Average price | $266 |
Good round-trip deal | $300 or less |
Good one-way deal | $358 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 December 18, 2025.
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
Sat 1/17
7:45 am-11:10 am
Nonstop2h 25m
Boston Logan Intl
Tue 1/20
3:35 pm-5:43 pm
Nonstop3h 08m
$127
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 1/20
5:35 pm-8:50 pm
Nonstop2h 15m
Boston Logan Intl
Thu 1/22
5:30 am-7:20 am
Nonstop2h 50m
$132
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 1/17
5:15 am-4:28 pm
1 stop10h 13m
Boston Logan Intl
Tue 1/20
3:35 pm-5:43 pm
Nonstop3h 08m
$136
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 1/7
5:00 pm-8:21 pm
Nonstop2h 21m
Boston Logan Intl
Sun 1/11
7:55 pm-10:01 pm
Nonstop3h 06m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 1/9
7:30 am-10:52 am
Nonstop2h 22m
Boston Logan Intl
Sun 1/11
10:30 am-12:34 pm
Nonstop3h 04m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 4/18
6:26 pm-9:51 pm
Nonstop2h 25m
Boston Logan Intl
Wed 4/22
3:39 pm-5:31 pm
Nonstop2h 52m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 1/10
2:00 pm-5:29 pm
Nonstop2h 29m
Boston Logan Intl
Sun 1/11
7:55 pm-10:01 pm
Nonstop3h 06m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 1/12
7:30 am-10:52 am
Nonstop2h 22m
Boston Logan Intl
Wed 1/14
4:16 pm-6:16 pm
Nonstop3h 00m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 1/7
7:45 am-11:10 am
Nonstop2h 25m
Boston Logan Intl
Wed 1/14
3:35 pm-5:43 pm
Nonstop3h 08m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 1/24
7:05 am-10:40 am
Nonstop2h 35m
Boston Logan Intl
Sun 1/25
7:30 am-9:41 am
Nonstop3h 11m
$137
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 December 18, 2025.
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 40% versus a flight in the morning.
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 December 16, 2024.
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.
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 December 18, 2025.
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.
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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 December 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$163 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$221 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$411 | FlexibilityNo cancel fee | On-time63% |