What is the cheapest airline that flies from Chicago to Maine?

Delta, Southwest, and JetBlue are the most popular carriers operating from Chicago to Maine

How many flights depart from Chicago to Maine on average per week?

389 flights are operational weekly from Chicago to Maine as of September 2026. The most popular departure day for this route is Fri, with 24% of flights per week taking off on this day.

How many flights depart from Chicago to Maine on average per day?

As of September 2026, there are 55 flights per day flying from Chicago to Maine. The most common time of day flights depart is 7:00PM, with 42% of flights taking off in the afternoon.

When did momondo last update prices for flights from Chicago to Maine?

Prices for flights from Chicago to Maine were last updated today.

How many operators does momondo search for flights from Chicago to Maine?

The number of operators available for flights from Chicago to Maine is 5 as of September 2026.

How old do you have to be to fly from Chicago to Maine?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maine.

What documentation or ID do you need to fly to Maine?

The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$108 Cheap Flights from Chicago to Maine in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Maine

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:24 pm - 12:23 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 59mnonstop

11:47 am - 7:31 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

20h 44m1 stop Orlando

$212Multiple Airlines

Tue, Oct 6 - Sat, Oct 17

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

11:57 am - 1:11 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

26h 14m1 stop Orlando

$212Multiple Airlines

Sat, Dec 5 - Mon, Dec 7

9:39 am - 1:07 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$213JetBlue

Wed, Oct 7 - Mon, Oct 12

8:24 pm - 12:23 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 59mnonstop

5:12 pm - 7:14 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$214JetBlue

Wed, Oct 7 - Tue, Oct 13

9:00 am - 12:39 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

5:45 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 20mnonstop

$216American Airlines

Tue, Sep 29 - Tue, Sep 29

7:00 am - 10:33 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

7:23 pm - 9:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

$217American Airlines

Tue, Oct 6 - Wed, Oct 7

7:50 pm - 11:24 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

6:43 pm - 8:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

$217United Airlines

Thu, Oct 1 - Mon, Oct 5

1:59 pm - 5:24 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

8:25 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$217United Airlines

Tue, Oct 27 - Mon, Nov 2

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

4:25 pm - 6:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

$217Delta

Sat, Oct 24 - Tue, Oct 27

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

1:35 pm - 3:27 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$217Delta

Thu, Oct 22 - Sat, Oct 24

Cheap last minute flights

Enter your travel dates to find the best prices.

3:50 pm - 10:51 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 01m1 stop Orlando

12:52 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 31m1 stop Atlanta Hartsfield-Jackson

$243Frontier

Fri, Sep 11 - Tue, Sep 22

3:50 pm - 10:22 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

17h 32m1 stop Orlando

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

$246Frontier

Wed, Sep 9 - Sat, Sep 12

6:45 pm - 10:27 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

8:33 am - 10:35 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$266American Airlines

Fri, Sep 11 - Tue, Sep 22

9:38 am - 1:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

5:00 pm - 7:01 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

$286JetBlue

Wed, Sep 9 - Tue, Sep 15

8:24 pm - 12:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

5:00 pm - 7:01 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

$286JetBlue

Thu, Sep 10 - Tue, Sep 15

5:45 am - 9:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

5:50 am - 7:25 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$287Southwest

Mon, Sep 7 - Mon, Oct 5

5:18 pm - 9:00 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

7:00 am - 9:06 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

$295American Airlines

Wed, Sep 9 - Sat, Sep 19

5:45 am - 9:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

8:40 am - 10:15 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$295Southwest

Fri, Sep 11 - Sat, Sep 19

10:29 am - 2:05 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

8:50 pm - 10:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

$295Delta

Fri, Sep 11 - Wed, Sep 16

7:30 pm - 11:09 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

$295Delta

Wed, Sep 9 - Thu, Sep 17

Cheap direct flights

Enter your travel dates to find the best prices.

9:39 am - 1:07 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$213JetBlue

Wed, Oct 7 - Mon, Oct 12

8:24 pm - 12:23 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 59mnonstop

5:12 pm - 7:14 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$214JetBlue

Wed, Oct 7 - Tue, Oct 13

9:00 am - 12:39 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

5:45 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 20mnonstop

$216American Airlines

Tue, Sep 29 - Tue, Sep 29

3:48 pm - 7:33 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

5:54 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

$217American Airlines

Sat, Oct 10 - Mon, Oct 12

7:50 pm - 11:24 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

6:43 pm - 8:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

$217United Airlines

Thu, Oct 1 - Mon, Oct 5

1:59 pm - 5:24 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

8:25 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$217United Airlines

Tue, Oct 27 - Mon, Nov 2

5:30 am - 8:55 amMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

5:50 am - 7:25 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$217Southwest

Mon, Oct 5 - Thu, Oct 8

6:00 pm - 9:25 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

6:40 pm - 8:25 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$217Southwest

Tue, Sep 22 - Thu, Sep 24

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

6:45 pm - 8:46 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

$217Delta

Wed, Oct 28 - Sat, Oct 31

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

6:45 pm - 8:46 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

$217Delta

Sat, Oct 31 - Sat, Oct 31

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Frontier flights from Chicago to Maine

Our best Frontier deals on Chicago to Maine flight tickets

Frontier

Dec 3

MDW8:07 pmChicago Midway

13h 55m

1 stop

BOS11:02 amBoston Logan Intl

Dec 14

BOS11:57 amBoston Logan Intl

8h 05m

1 stop

MDW7:02 pmChicago Midway

$221

Frontier

Sep 25

ORD3:50 pmChicago O'Hare Intl

18h 01m

1 stop

BOS10:51 amBoston Logan Intl

Sep 29

BOS12:52 pmBoston Logan Intl

6h 31m

1 stop

ORD6:23 pmChicago O'Hare Intl

$222

Frontier

Sep 19

ORD3:50 pmChicago O'Hare Intl

18h 08m

1 stop

BOS10:58 amBoston Logan Intl

Sep 22

BOS12:52 pmBoston Logan Intl

6h 31m

1 stop

ORD6:23 pmChicago O'Hare Intl

$225

Southwest flights from Chicago to Maine

Our best Southwest deals on Chicago to Maine flight tickets

Southwest

Oct 21

MDW7:50 amChicago Midway

2h 20m

BOS11:10 amBoston Logan Intl

Oct 27

BOS5:55 pmBoston Logan Intl

2h 35m

MDW7:30 pmChicago Midway

$217

Southwest

Oct 16

MDW6:45 pmChicago Midway

2h 20m

BOS10:05 pmBoston Logan Intl

Oct 26

BOS10:00 pmBoston Logan Intl

2h 40m

MDW11:40 pmChicago Midway

$226

Southwest

Oct 21

MDW1:10 pmChicago Midway

2h 20m

BOS4:30 pmBoston Logan Intl

Oct 26

BOS7:30 pmBoston Logan Intl

5h 25m

1 stop

MDW11:55 pmChicago Midway

$227

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Tue 10/6

8:24 pm-12:23 am

Nonstop2h 59m

Boston Logan Intl

Sat 10/17

11:47 am-7:31 am

1 stop20h 44m

$212

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sat 12/5

5:46 pm-9:14 pm

Nonstop2h 28m

Boston Logan Intl

Mon 12/7

11:57 am-1:11 pm

1 stop26h 14m

$212

Quickest round-trip

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Wed 10/7

9:39 am-1:07 pm

Nonstop2h 28m

Boston Logan Intl

Mon 10/12

6:55 am-8:47 am

Nonstop2h 52m

$213

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Wed 10/7

8:24 pm-12:23 am

Nonstop2h 59m

Boston Logan Intl

Tue 10/13

5:12 pm-7:14 pm

Nonstop3h 02m

$214

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Tue 9/29

9:00 am-12:39 pm

Nonstop2h 39m

Boston Logan Intl

Tue 9/29

5:45 pm-8:05 pm

Nonstop3h 20m

$216

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Tue 10/6

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Wed 10/7

7:23 pm-9:29 pm

Nonstop3h 06m

$217

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Thu 10/1

7:50 pm-11:24 pm

Nonstop2h 34m

Boston Logan Intl

Mon 10/5

6:43 pm-8:40 pm

Nonstop2h 57m

$217

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Tue 10/27

1:59 pm-5:24 pm

Nonstop2h 25m

Boston Logan Intl

Mon 11/2

8:25 pm-10:29 pm

Nonstop3h 04m

$217

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sat 10/24

7:25 am-11:00 am

Nonstop2h 35m

Boston Logan Intl

Tue 10/27

4:25 pm-6:20 pm

Nonstop2h 55m

$217

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Thu 10/22

7:25 am-11:00 am

Nonstop2h 35m

Boston Logan Intl

Sat 10/24

1:35 pm-3:27 pm

Nonstop2h 52m

$217

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Maine?

The cheapest month to fly to Maine from Chicago is in April. Flight prices, which tend to average around $334, are often lower during this time because this is during the off-season. If you aren’t able to travel to Maine during the month of April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $337.

What is the cheapest day to depart on your flight to Maine?

The cheapest day to depart from Chicago to Maine is on a Wednesday. Travelers who choose to depart for Maine on a Wednesday will often find tickets for as low as $341. Flights from Chicago to Maine on a Sunday will generally be more expensive and average around $455. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Maine?

The cheapest time of day to fly to Maine is in the evening when flights can be purchased for as low as $301. Flights in the afternoon are often more expensive with an average ticket price of $396.

What is the cheapest Chicago to Maine flight route?

Fly from Chicago O'Hare Intl to Portland for the best Chicago - Maine flight prices

How far in advance should I book a flight from Chicago to Maine?

You are more likely to see cheaper flights to Maine from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Maine for around $382 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maine from Chicago for as low as $287 on momondo.

What cabin class options are available on Chicago to Maine flights?

There are 4 cabin classes available to choose from on Chicago to Maine flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to Maine flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maine

Best Price Found	$108
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Maine	49 airports

The best one-way flight to Maine from Chicago in the past 72 hours is $108. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $212.

The fastest flight from Chicago to Maine takes 2h 10m

Direct flights go from Chicago to Maine every day.

There are 49 airports in Maine. From Chicago there are direct flights to Portland (PWM), Boston Logan Intl (BOS).

Search flight deals

Frequently asked questions about flying from Chicago to Maine

When did momondo last update prices for flights from Chicago to Maine?
Prices for flights from Chicago to Maine were last updated today.
How many operators does momondo search for flights from Chicago to Maine?
The number of operators available for flights from Chicago to Maine is 5 as of September 2026.
How old do you have to be to fly from Chicago to Maine?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maine.
What documentation or ID do you need to fly to Maine?
The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Maine?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Maine is Embraer 175, representing 29.27% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 23.01%, Boeing 737 MAX 8 at 17.77%, and Airbus A319 at 10.59%.

Best airlines flying from Chicago to Maine

Compare and see reviews for airlines that fly from Chicago to Maine with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.4 10,171 reviews		Search United Airlines flights
American Airlines	PriceFrom $229	Free Cancellation	Rating 7.1 12,044 reviews		Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maine?

It is quick and easy to find Chicago to Maine flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maine that suits you.

Can I find flights from Chicago to Maine with flexible booking policies on momondo?

Yes. All flights to Maine from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Maine?

Once all potential Chicago to Maine flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Maine right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Maine flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.