$55 Find Cheap Flights from Illinois to Maine

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Low seasonJanuary
High seasonAugust
Cheapest flight$55
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Illinois to Maine

  • How does KAYAK find such low prices on flights from Illinois to Maine?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Maine.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Maine?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Maine is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Maine?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Illinois to Maine with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Maine?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Illinois to Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Maine?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Maine is Portland Airport (PWM), with an average flight price of $195.

  • What is the cheapest day to fly to Maine?

    Based on KAYAK data, the cheapest day to fly to Maine is Tuesday where round-trip tickets can be as cheap as $274. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $391 on average.

  • What is the cheapest time of day to fly to Maine?

    The cheapest time of day to fly to Maine is generally in the afternoon, when round-trip flights cost $278 on average. Morning departures are around 31% more expensive than evening flights, on average. The most expensive time of day to fly to Maine is generally in the morning, which is peak travel time and where the average cost of a ticket is $368.

  • What is the cheapest flight to Maine?

    The cheapest ticket to Maine from Illinois found in the last 72 hours was to Portland, at $195 round-trip. The most popular route is Chicago Midway Airport (MDW) to Portland (PWM) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $195.

  • What is the cheapest month to fly from Illinois to Maine?

    The cheapest month for flights from Illinois to Maine is August, when tickets cost $293 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $519 and $469 respectively.

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

    To get a below average price on the flight from Illinois to Maine, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

  • How long is the flight to Maine?

    An average nonstop flight from Illinois to Maine takes 7h 02m, covering a distance of 1005 miles. The shortest route is Chicago Midway Airport (MDW) to Portland (PWM) with an average flight time of 2h 10m.

  • What are the most popular destinations in Maine?

    Based on KAYAK flight searches, the most popular destination is Boston (78% of total searches to Maine). The next most popular destinations are Portland (15%) and Bangor (7%). Searches for flights to Rockland (0%), to Bar Harbor (0%) and to Augusta (0%) are also popular.

Top 5 airlines serving from Illinois to Maine

 
Need help choosing which airline to fly with from Illinois to Maine? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4278 reviews
8.6Crew
8.0Comfort
7.1Food
8.2Boarding
7.6Entertainment
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Book cheap flights from Illinois to Maine

Recent round-trip flight deals

7/8Tue
1 stopSpirit Airlines
12h 01mORD-BOS
7/9Wed
1 stopSpirit Airlines
13h 16mBOS-ORD
$112
7/8Tue
1 stopSpirit Airlines
12h 01mORD-BOS
7/9Wed
1 stopSpirit Airlines
13h 16mBOS-ORD
$114
7/21Mon
nonstopSouthwest
2h 15mMDW-BOS
7/24Thu
nonstopSouthwest
2h 35mBOS-MDW
$123
9/5Fri
nonstopSouthwest
2h 15mMDW-BOS
9/7Sun
nonstopSouthwest
2h 35mBOS-MDW
$125
7/30Wed
nonstopAmerican Airlines
2h 44mORD-BOS
8/6Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$139
7/14Mon
nonstopAmerican Airlines
2h 44mORD-BOS
7/16Wed
nonstopAmerican Airlines
2h 58mBOS-ORD
$141
7/1Tue
nonstopUnited Airlines
2h 27mORD-BOS
7/8Tue
1 stopUnited Airlines
5h 37mBOS-ORD
$143
9/5Fri
nonstopUnited Airlines
2h 30mORD-BOS
9/7Sun
1 stopUnited Airlines
5h 06mBOS-ORD
$159
6/26Thu
1 stopFrontier
7h 37mMDW-BOS
6/29Sun
1 stopFrontier
17h 32mBOS-MDW
$200
6/26Thu
1 stopFrontier
23h 26mORD-BOS
6/30Mon
1 stopFrontier
17h 29mBOS-ORD
$201

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Recent one-way flight deals

7/8Tue
1 stopSpirit Airlines
12h 01mORD-BOS
$55
7/9Wed
1 stopSpirit Airlines
8h 30mORD-BOS
$57
8/21Thu
nonstopSouthwest
2h 15mMDW-BOS
$63
7/17Thu
nonstopSouthwest
2h 15mMDW-BOS
$69
10/14Tue
nonstopUnited Airlines
2h 26mORD-BOS
$86
8/24Sun
nonstopUnited Airlines
2h 26mORD-BOS
$89
8/30Sat
nonstopAmerican Airlines
2h 34mORD-BOS
$93
7/24Thu
nonstopAmerican Airlines
2h 44mORD-BOS
$97
6/27Fri
1 stopFrontier
7h 55mORD-BOS
$100
6/26Thu
1 stopFrontier
7h 37mMDW-BOS
$100

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Last minute flights from Illinois to Maine

Last minute flight, train and bus deals

6/20Fri
nonstopAmerican Airlines
2h 40mORD-BOS
6/25Wed
nonstopAmerican Airlines
2h 54mBOS-ORD
$137
6/20Fri
nonstopSouthwest
2h 15mMDW-BOS
6/24Tue
nonstopSouthwest
2h 40mBOS-MDW
$137
6/21Sat
multi-stopFrontier
11h 24mORD-BOS
6/27Fri
multi-stopFrontier
17h 29mBOS-ORD
$220
6/20Fri
multi-stopFrontier
7h 55mORD-BOS
6/28Sat
multi-stopFrontier
14h 03mBOS-ORD
$229
6/21Sat
multi-stopUnited Airlines
6h 28mORD-BOS
6/24Tue
nonstopUnited Airlines
2h 58mBOS-ORD
$257
6/20Fri
nonstopJetBlue
2h 24mORD-BOS
6/23Mon
nonstopJetBlue
2h 55mBOS-ORD
$268
6/20Fri
nonstopUnited Airlines
2h 35mORD-BOS
7/31Thu
nonstopUnited Airlines
2h 58mBOS-ORD
$291
6/20Fri
nonstopJetBlue
2h 24mORD-BOS
6/24Tue
nonstopJetBlue
2h 55mBOS-ORD
$303
6/21Sat
nonstopDelta
2h 31mORD-BOS
6/24Tue
nonstopDelta
3h 00mBOS-ORD
$323
6/21Sat
multi-stopDelta
6h 54mMDW-BOS
6/26Thu
multi-stopDelta
6h 31mBOS-MDW
$329

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Everything you need to know for your flight to Maine

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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