Cheap flights from Chicago (CHI) to Maine

CHI — PWM
Oct 4 — Oct 111

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

To save up to 35% on this flight, we recommend booking at least 49 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Maine from $431 1-2 weeks out and tickets from $529 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago to Maine?

September is one of the best times of the year to fly to Maine from Chicago. Prices for September average $388 per person but you can even find prices for as low as $174. The most expensive prices can be found in the month of December. Opting for a September flight can save you 19% on your journey compared to booking in December

When is the cheapest time to fly from Chicago to Maine (CHI - ME)?

When flying from Chicago to Maine, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to Maine in September, October 2022

The best prices found for CHI to Maine flights for September, October
Oct 29 - Nov 1
MDW

Chicago Midway

PWM

Portland

1 stop

12h 50m
PWM

Portland

MDW

Chicago Midway

1 stop

4h 27m
$208

Multiple Airlines

Pick Dates

Deal found 27/9/22

Oct 26 - Nov 2
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 19m
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

4h 55m
$222

United Airlines

Pick Dates

Deal found 26/9/22

Oct 22 - Oct 26
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

10h 40m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 48m
$224

Multiple Airlines

Pick Dates

Deal found 26/9/22

Chicago to Maine 2022 flight deals

Cheap flights to Maine from Chicago found for this year
Nov 2 - Nov 5
MDW

Chicago Midway

PWM

Portland

1 stop

4h 22m
PWM

Portland

MDW

Chicago Midway

1 stop

13h 12m
$204

Multiple Airlines

Pick Dates

Deal found 27/9/22

Oct 29 - Nov 1
MDW

Chicago Midway

PWM

Portland

1 stop

12h 50m
PWM

Portland

MDW

Chicago Midway

1 stop

4h 27m
$208

Multiple Airlines

Pick Dates

Deal found 27/9/22

Oct 26 - Nov 2
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 19m
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

4h 55m
$222

United Airlines

Pick Dates

Deal found 26/9/22

Cheap United Airlines flights from Chicago to Maine

Jan 17 - Jan 24
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 29m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

3h 20m
$218

United Airlines

Pick Dates

Deal found 27/9/22

Jan 10 - Jan 17
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

4h 41m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
$227

United Airlines

Pick Dates

Deal found 27/9/22

Oct 26 - Oct 29
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 19m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
$228

United Airlines

Pick Dates

Deal found 28/9/22

Cheap Delta flights from Chicago to Maine

Jan 17 - Jan 25
MDW

Chicago Midway

PWM

Portland

1 stop

5h 05m
PWM

Portland

MDW

Chicago Midway

1 stop

4h 16m
$236

Delta

Pick Dates

Deal found 27/9/22

Oct 11 - Oct 18
MDW

Chicago Midway

PWM

Portland

2 stops

9h 08m
PWM

Portland

MDW

Chicago Midway

1 stop

4h 12m
$240

Delta

Pick Dates

Deal found 26/9/22

Oct 26 - Nov 5
MDW

Chicago Midway

PWM

Portland

1 stop

7h 31m
PWM

Portland

MDW

Chicago Midway

1 stop

8h 28m
$246

Delta

Pick Dates

Deal found 28/9/22

Non-stop flights to Maine from Chicago

Save time with Chicago to Maine direct flight deals
Jan 17 - Jan 24
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 29m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

3h 20m
$218

United Airlines

Pick Dates

Deal found 27/9/22

Jan 10 - Jan 17
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 14m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
$228

United Airlines

Pick Dates

Deal found 27/9/22

Jan 7 - Jan 14
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 29m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
$238

United Airlines

Pick Dates

Deal found 27/9/22

Last minute flights from Chicago to Maine

Late deals on return flights to Maine from Chicago, departing today and this week
Oct 8 - Oct 12
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

11h 45m
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

4h 55m
$404

United Airlines

Pick Dates

Deal found 27/9/22

Oct 8 - Oct 12
ORD

Chicago O'Hare Intl

PWM

Portland

2 stops

15h 05m
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

4h 55m
$408

United Airlines

Pick Dates

Deal found 27/9/22

Oct 4 - Oct 5
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

7h 54m
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
$415

United Airlines

Pick Dates

Deal found 27/9/22

One-way flights to Maine from Chicago

The cheapest one-way flights from Chicago to Maine
Oct 28
MDW

Chicago Midway

BGR

Bangor

1 stop

14h 32m
$103

Multiple Airlines

Pick Dates

Deal found 26/9/22

Oct 18
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 22m
$109

United Airlines

Pick Dates

Deal found 29/9/22

Nov 8
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

15h 49m
$115

Frontier

Pick Dates

Deal found 28/9/22

Related info for your journey

Useful info, stats and facts about Chicago to Maine flights.

Which airlines flying from Chicago to Maine have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, United Airlines, and Delta flying from Chicago to Maine have implemented new flexible cancellation policies.

Can I find flights from Chicago to Maine for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Maine for under $300. The cheapest flight booked recently is on Multiple Airlines for just $204, but on average you can expect to pay $233.

Are there nonstop flights from Chicago to Maine for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Maine under $300. A good price for a nonstop flight from Chicago to Maine is less than $277.

Are there last-minute flights available from Chicago to Maine for under $500?

There are currently 20+ open flights from Chicago to Maine within the next 7 days for less than $500.

What days are nonstop flights available from Chicago to Maine?

Nonstop flights are available for this route on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

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

16 flight departures from Chicago to Maine per day on average.
Morning (6am - Noon) - 19% of flight departures
Afternoon (Noon - 6pm) - 69% of flight departures
Evening (6pm - Midnight) - 13% of flight departures

How long is the flight from Chicago to Maine?

Departing from Chicago to Maine will take you 2h 29m. Chicago and Maine are separated by a distance of 902 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines to fly from Chicago to Maine one-way?

One-way options have recently been found by users for as low as $109 on United Airlines. Other airlines that offer cheap prices include Frontier from $115 and American Airlines from $117 one-way.

What are the most popular routes from Chicago to Maine?

While some choose either Chicago Midway - Portland or Chicago O'Hare Intl - Bangor, Chicago O'Hare Intl - Portland is the most popular route from Chicago to Maine.

What are the most popular airlines that fly from Chicago to Maine?

The most popular airlines flying from Chicago to Maine are American Airlines, Delta and Juneyao Airlines. Something to consider prior to booking your flight.

What are the most reliable airlines from Chicago to Maine?

The top 3 most reliable airlines when flying from Chicago to Maine are Air Wisconsin (89%), United Airlines (85%) and Air New Zealand (85%).

What are the cheapest flights from Chicago to Maine?

The cheapest flight price from Chicago to Maine is $173. On average you can expect to pay $564. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $233.

Destination points for flights from Chicago to Maine

Select to see more specific information for flights from Chicago to all places in Maine

Top 4 airlines flying from Chicago to Maine

The chart below displays the airlines Cheapflights users traveling from Chicago to Maine choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$16Average$23FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
American AirlinesCheapest$127Average$406FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
DeltaCheapest$137Average$363FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$154Average$446FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Chicago to Maine

See what time of day planes typically take off from Chicago to Maine
1%of flight departuresEarly morningMidnight to 6 am
39%of flight departuresMorning6 am to noon
60%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM