$85 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 8/18. 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
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Maine to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maine to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Maine to Chicago

Sat, Aug 22 - Thu, Aug 27
Southwest Logo
8:40 am - 10:15 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
$175Southwest
Mon, Aug 10 - Sat, Aug 15
JetBlue Logo
5:01 am - 8:52 am
BOS
-
ORD
4h 51m
1 stop
JetBlue Logo
9:40 am - 5:17 pm
ORD
-
BOS
6h 37m
1 stop
$177JetBlue
Sat, Jul 11 - Mon, Jul 13
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
Delta Logo
6:59 am - 10:30 am
ORD
-
BOS
2h 31mnonstop
$178Delta
Thu, Jul 9 - Wed, Jul 15
United Airlines Logo
8:15 am - 10:12 am
BOS
-
ORD
2h 57mnonstop
United Airlines Logo
10:30 am - 2:07 pm
ORD
-
BOS
2h 37mnonstop
$179United Airlines
Sat, Aug 1 - Wed, Aug 5
Delta Logo
7:59 pm - 9:59 pm
BOS
-
ORD
3h 00mnonstop
Delta Logo
7:30 pm - 11:00 pm
ORD
-
BOS
2h 30mnonstop
$183Delta
Tue, Jul 28 - Tue, Aug 4
United Airlines Logo
7:27 pm - 11:31 pm
BOS
-
ORD
5h 04m
1 stop
United Airlines Logo
6:05 am - 9:29 am
ORD
-
BOS
2h 24mnonstop
$184United Airlines
Wed, Jul 22 - Tue, Jul 28
American Airlines Logo
5:03 pm - 11:30 pm
BGR
-
ORD
7h 27m
1 stop
American Airlines Logo
7:08 pm - 10:57 pm
ORD
-
BGR
2h 49mnonstop
$271American Airlines
Wed, Jul 22 - Tue, Jul 28
American Airlines Logo
12:59 pm - 3:10 pm
BGR
-
ORD
3h 11mnonstop
American Airlines Logo
7:08 pm - 10:57 pm
ORD
-
BGR
2h 49mnonstop
$275American Airlines
Fri, Jul 10 - Mon, Jul 13
Multiple Airlines Logo
3:07 pm - 10:12 am
AUG
-
ORD
20h 05m
1 stop
Multiple Airlines Logo
9:41 pm - 10:26 am
ORD
-
AUG
11h 45m
1 stop
$440Multiple Airlines
Tue, Jul 7 - Sat, Jul 11
Multiple Airlines Logo
9:00 am - 9:03 pm
AUG
-
ORD
13h 03m
2 stops
Multiple Airlines Logo
1:09 pm - 8:40 pm
ORD
-
AUG
6h 31m
1 stop
$463Multiple Airlines
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Good to know

Low seasonJanuary
Cheapest flight$85
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

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.
First Class flights to Chicagofrom $725
Business Class flights to Chicagofrom $1,040
Premium Economy Class flights to Chicagofrom $1,087
Economy Class flights to Chicagofrom $289