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$60 Find Cheap Flights from Maine to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

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In the last 7 days travelers have searched 46,479,581 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

October

Cheapest flight

$60
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Portland to Chicago O'Hare Airport

FAQs for booking flights from Maine to Chicago

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

    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 Maine to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from 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 Maine to Chicago?

    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 to Chicago with an airline and back to Maine with another airline.

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

    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 to Chicago from Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Maine to Chicago?

Find which airlines fly direct from Maine to Chicago, which days they fly and book direct flights.

Nonstop departures

Maine to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Maine

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Book cheap flights from Maine to Chicago

Recent round-trip flight deals

11/16sam.
1 stopFrontier
12h 41mBOS-ORD
11/18lun.
1 stopFrontier
9h 54mORD-BOS
$108
11/12mar.
1 stopSpirit Airlines
7h 30mBOS-ORD
11/18lun.
nonstopSpirit Airlines
2h 19mORD-BOS
$109
11/19mar.
1 stop
8h 17mBOS-ORD
11/21jeu.
nonstop
2h 19mORD-BOS
$113
11/16sam.
1 stop
12h 41mBOS-ORD
11/21jeu.
nonstop
2h 19mORD-BOS
$114
12/5jeu.
nonstopDelta
2h 58mBOS-ORD
12/12jeu.
nonstopDelta
2h 30mORD-BOS
$117
11/16sam.
nonstopSouthwest
2h 50mBOS-MDW
11/23sam.
nonstopSouthwest
2h 10mMDW-BOS
$118
12/13ven.
nonstopJetBlue
3h 06mBOS-ORD
1/9jeu.
nonstopJetBlue
2h 30mORD-BOS
$120
12/9lun.
nonstopJetBlue
3h 06mBOS-ORD
12/9lun.
1 stopJetBlue
4h 29mORD-BOS
$121
12/13ven.
nonstopSouthwest
2h 45mBOS-MDW
12/15dim.
nonstopSouthwest
2h 10mMDW-BOS
$124
11/13mer.
nonstopDelta
3h 01mBOS-ORD
11/17dim.
nonstopDelta
2h 20mORD-BOS
$130

Search by stops

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Recent one-way flight deals

1/30jeu.
1 stopFrontier
13h 50mPWM-ORD
$60
2/6jeu.
1 stopFrontier
18h 40mPWM-MDW
$61
11/13mer.
1 stopSpirit Airlines
9h 37mBOS-ORD
$76
1/7mar.
1 stopSpirit Airlines
27h 36mBOS-ORD
$77
1/10ven.
nonstopSouthwest
2h 55mBOS-MDW
$79
1/10ven.
nonstopDelta
3h 08mBOS-ORD
$79
11/6mer.
nonstopSouthwest
2h 45mBOS-MDW
$81
11/6mer.
nonstopJetBlue
3h 06mBOS-ORD
$81
1/3ven.
nonstopDelta
3h 03mBOS-ORD
$100
4/29mar.
1 stopJetBlue
5h 06mPWM-ORD
$103

Search by stops

Search by airline

Search by price

Last minute flights from Maine to Chicago

Last minute flight, train and bus deals

11/2sam.
multi-stopFrontier
8h 34mBOS-ORD
11/6mer.
multi-stopFrontier
9h 02mORD-BOS
$100
11/2sam.
multi-stopFrontier
8h 34mBOS-ORD
11/7jeu.
multi-stopFrontier
4h 26mORD-BOS
$103
11/2sam.
multi-stop
8h 34mBOS-ORD
11/8ven.
nonstop
2h 19mORD-BOS
$126
11/2sam.
multi-stop
8h 34mBOS-ORD
11/4lun.
multi-stop
7h 39mORD-BOS
$133
11/5mar.
nonstopJetBlue
3h 06mBOS-ORD
11/9sam.
nonstopJetBlue
2h 18mORD-BOS
$161
11/5mar.
nonstopDelta
2h 51mBOS-ORD
11/10dim.
nonstopDelta
2h 24mORD-BOS
$169
11/5mar.
multi-stopJetBlue
5h 02mBOS-ORD
11/9sam.
nonstopJetBlue
2h 18mORD-BOS
$170
11/5mar.
multi-stopSpirit Airlines
26h 14mBOS-ORD
11/7jeu.
nonstopSpirit Airlines
2h 18mORD-BOS
$189
11/4lun.
nonstopSpirit Airlines
2h 52mBOS-ORD
11/14jeu.
nonstopSpirit Airlines
2h 18mORD-BOS
$195
11/3dim.
multi-stopDelta
4h 49mBOS-ORD
11/7jeu.
nonstopDelta
2h 24mORD-BOS
$247

Search by stops

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maine

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