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Cheap flights from Maine (ME) to Chicago (CHI)

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How to find the cheapest flight from
Maine to Chicago (CHI)

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

Travelers have found it’s best to book a flight 20 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 20 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Maine to Chicago 1-2 weeks in advance for as low as $137, or $157 for flights within the next 24 hours.

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

Flights from Maine to Chicago lean towards being more expensive in December. Prices are generally better when you fly from Maine to Chicago in April, with the cheapest ticket starting at $33.

Cheap flights from Maine to Chicago in October, November 2020

The best prices found for Maine to CHI flights for October, November
26 Nov - 2 Dec
$233pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland
26 Nov - 2 Dec
$241pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
22 Nov - 2 Dec
$249pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland

Maine to Chicago 2020 flight deals

Cheap flights to Chicago from Maine found for this year
26 Nov - 2 Dec
$233pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland
15 Dec - 9 Jan
$235pp
BGR
Bangor
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BGR
Bangor
15 Dec - 9 Jan
$238pp
BGR
Bangor
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BGR
Bangor

Non-stop flights to Chicago from Maine

Save time with Maine to Chicago direct flight deals
16 Nov - 28 Nov
$269pp
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
25 Nov - 1 Dec
$281pp
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
24 Nov - 27 Nov
$313pp
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland

Last minute flights from Maine to Chicago

Late deals on round-trip flights to Chicago from Maine, departing today and this week
3 Nov - 4 Nov
$324pp
PWM
Portland
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
6 Nov - 11 Nov
$329pp
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
6 Nov - 11 Nov
$332pp
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland

One-way flights to Chicago from Maine

The cheapest one-way flights from Maine to Chicago
2:34 am - 7:24 am
Major Airline
1 Stop
5h 50m
PWM - ORD
Major Airline
$144
StudentUniverse
7:38 am - 3:58 pm
Delta
1 Stop
9h 20m
PWM - ORD
Delta
$225
Delta
11:12 am - 4:38 pm
American Airlines
1 Stop
6h 26m
PWM - ORD
American Airlines

Related info for your journey

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

Flight FAQs

From Maine to Chicago

Are flight prices decreasing from Maine to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Maine and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Maine to Chicago to control the spread of COVID-19?

JetBlue and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Maine to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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

United Airlines, American Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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

Yes, there are multiple flights from Maine to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $233, but on average you can expect to pay $259.

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

Cheapflights has at least 20 direct flights from Maine to Chicago under $300. A good price for a nonstop flight from Maine to Chicago is less than $365.

Are there last-minute flights available from Maine to Chicago for under $400?

There are currently 20+ open flights from Maine to Chicago within the next 7 days for less than $400.

What days are nonstop flights available from Maine to Chicago?

Nonstop flights can be found on the following days: Sunday, Monday, Wednesday, Thursday, Friday, Saturday.

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

When booking a flight from Maine to Chicago, you may want to consider flying on American Airlines, JetBlue or Delta as they are the most popular for this route.

What are the most popular routes from Maine to Chicago?

The most popular flight routes from Maine to Chicago are Portland - Chicago O'Hare Intl, Bangor - Chicago O'Hare Intl and Portland - Chicago Midway.

What are the cheapest Flights from Maine to Chicago?

The cheapest flight price from Maine to Chicago is $160. On average you can expect to pay $362. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $307.

What are the most reliable airlines from Maine to Chicago?

No one likes to see their flight delayed. When booking a flight from Maine to Chicago consider choosing SkyWest Airlines (98%), Qatar Airways (97%) or Air New Zealand (97%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Maine to Chicago?

Departing from Maine to Chicago will take you 2h 46m. This flight may include one or multiple stops.

What are the cheapest airlines flying from Maine to Chicago round-trip?

Our cheapest airline available from Maine to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $235 on this airline. Additional options worth looking into are United Airlines and Major Airline, starting at $261 and $283 round-trip.

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

$125 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Major Airline and United Airlines, with prices starting from $139 and $157, respectively.

Arrival points for flights from Maine to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Maine to Chicago
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing

Bar Harbor (BHB)
Presque Isle (PQI)
Portland (PWM)
Rockland (RKD)
Augusta (AUG)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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