Cheap flights from Maine to Chicago from $113
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maine to Chicago departing on 10/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Find the cheapest flights from Maine to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.American Airlines flights from Maine to Chicago
Our best American Airlines deals on Maine to Chicago flight tickets
United Airlines flights from Maine to Chicago
Our best United Airlines deals on Maine to Chicago flight tickets
momondo Fare Finder
Use the filters below to find and compare flights from Maine to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
BangorChicago
BGR Bangor - ORD Chicago O'Hare Intl
BGRORD
Bangor
Tue 12/8
6:23 am-11:34 am
1 stop6h 11m
Chicago O'Hare Intl
Sat 12/12
3:00 pm-10:38 pm
1 stop6h 38m
BangorChicago
BGR Bangor - ORD Chicago O'Hare Intl
BGRORD
Bangor
Tue 12/8
12:27 pm-7:56 pm
1 stop8h 29m
Chicago O'Hare Intl
Sat 12/12
3:19 pm-11:07 pm
1 stop6h 48m
BangorChicago
BGR Bangor - ORD Chicago O'Hare Intl
BGRORD
Bangor
Tue 12/8
12:06 pm-11:56 pm
2 stops12h 50m
Chicago O'Hare Intl
Sat 12/12
7:00 am-1:17 pm
1 stop5h 17m
BangorChicago
BGR Bangor - ORD Chicago O'Hare Intl
BGRORD
Bangor
Wed 11/4
5:02 pm-10:17 pm
1 stop6h 15m
Chicago O'Hare Intl
Wed 11/11
1:30 pm-11:25 pm
2 stops8h 55m
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 11/12
5:08 pm-7:05 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sun 11/15
6:18 pm-9:51 pm
Nonstop2h 33m
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 11/4
8:47 am-10:47 am
Nonstop3h 00m
Chicago O'Hare Intl
Fri 11/6
6:18 pm-9:52 pm
Nonstop2h 34m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 11/7
1:00 pm-7:40 pm
1 stop7h 40m
Chicago Midway
Wed 11/11
6:00 am-12:10 pm
1 stop5h 10m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 11/12
5:10 pm-11:15 pm
1 stop7h 05m
Chicago Midway
Sun 11/15
5:05 am-10:30 am
1 stop4h 25m
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 10/27
5:09 pm-12:51 pm
2 stops20h 42m
Chicago O'Hare Intl
Thu 10/29
9:51 am-9:08 am
1 stop22h 17m
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 11/25
5:09 pm-11:18 pm
2 stops31h 09m
Chicago O'Hare Intl
Tue 12/1
5:35 am-9:08 am
1 stop26h 33m
See travel insights to Chicago from
How to get the cheapest flight ticket from Maine to Chicago
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
What is the cheapest month to fly to Chicago?
The month of May is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $339. If you’re not able to fly to Chicago in May, then March is your next best option. Flight prices from Maine to Chicago during March average around $343.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $453. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Maine to Chicago for around $625.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maine to Chicago during this time can be as low as $412. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $506.
What is the cheapest Maine to Chicago flight route?
Fly from Portland to Chicago O'Hare Intl for the best Maine - Chicago flight prices
How far in advance should I book a flight from Maine to Chicago?
You are more likely to see cheaper flights to Chicago from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $382 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Maine for as low as $282 on momondo.
What cabin class options are available on Maine to Chicago flights?
There are 4 cabin classes available to choose from on Maine to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Maine to Chicago?
United Airlines, Delta, and Southwest are the most popular carriers operating from Maine to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Maine according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Maine to Chicago on average per day?
As of October 2026, 19 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 58% of daily flights taking off at noon.
How many flights depart from Maine to Chicago on average per week?
As of October 2026, there are 134 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.
Cheap Maine to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Maine to Chicago
Frequently asked questions about flying from Maine to Chicago
When did momondo last update prices for flights from Maine to Chicago?
Prices for flights from Maine to Chicago were last updated today.
How many operators does momondo search for flights from Maine to Chicago?
As of October 2026, there are 4 operators available to choose from for flights from Maine to Chicago.
How old do you have to be to fly from Maine to Chicago?
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 Maine to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Maine to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Maine to Chicago is Embraer 175 (23.23% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (18.47%), Boeing 737 MAX 9 (14.78%), and Boeing 737 MAX 8 (12.56%).
Best airlines flying from Maine to Chicago
Compare and see reviews for airlines that fly from Maine to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $209 | Free Cancellation | Rating 7.0 12,145 reviews | |||
| PriceFrom $234 | Free Cancellation | Rating 7.8 8,641 reviews | |||
| PriceFrom $238 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 7.9 4,221 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Maine to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Maine to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Maine to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Maine which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Maine to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Maine. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Maine to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Maine and alert you when they change.