$98 Find Cheap Flights from Maine to Chicago - Compare and Save

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

Wed, Oct 21 - Fri, Oct 23
Frontier Logo
11:28 am - 8:28 pm
BOS
-
ORD
10h 00m
1 stop
Frontier Logo
9:33 pm - 10:52 am
ORD
-
BOS
12h 19m
1 stop
$161Frontier
Wed, Oct 21 - Fri, Oct 23
Frontier Logo
11:28 am - 8:28 pm
BOS
-
ORD
10h 00m
1 stop
Frontier Logo
9:33 pm - 10:52 am
ORD
-
BOS
12h 19m
1 stop
$161Frontier
Tue, Oct 6 - Thu, Oct 8
JetBlue Logo
6:55 am - 8:49 am
BOS
-
ORD
2h 54mnonstop
JetBlue Logo
1:00 pm - 8:49 pm
ORD
-
BOS
6h 49m
1 stop
$199JetBlue
Tue, Oct 6 - Thu, Oct 8
JetBlue Logo
6:55 am - 8:49 am
BOS
-
ORD
2h 54mnonstop
JetBlue Logo
9:38 am - 1:06 pm
ORD
-
BOS
2h 28mnonstop
$208JetBlue
Sat, Oct 31 - Sat, Oct 31
Delta Logo
7:30 am - 9:24 am
BOS
-
ORD
2h 54mnonstop
Delta Logo
4:40 pm - 8:21 pm
ORD
-
BOS
2h 41mnonstop
$217Delta
Sat, Oct 17 - Wed, Oct 21
Delta Logo
7:30 am - 9:24 am
BOS
-
ORD
2h 54mnonstop
Delta Logo
7:10 pm - 10:53 pm
ORD
-
BOS
2h 43mnonstop
$217Delta
Wed, Oct 21 - Sat, Oct 24
American Airlines Logo
7:00 am - 9:05 am
BOS
-
ORD
3h 05mnonstop
American Airlines Logo
5:11 pm - 8:59 pm
ORD
-
BOS
2h 48mnonstop
$217American Airlines
Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
10:30 am - 12:32 pm
BOS
-
ORD
3h 02mnonstop
American Airlines Logo
8:24 pm - 11:59 pm
ORD
-
BOS
2h 35mnonstop
$217American Airlines
Wed, Oct 21 - Sat, Oct 24
United Airlines Logo
8:00 am - 9:56 am
BOS
-
ORD
2h 56mnonstop
United Airlines Logo
9:24 pm - 12:54 am
ORD
-
BOS
2h 30mnonstop
$217United Airlines
Sat, Sep 12 - Tue, Sep 15
United Airlines Logo
6:42 pm - 8:40 pm
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
1:55 pm - 5:36 pm
ORD
-
BOS
2h 41mnonstop
$217United Airlines
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Good to know

Low season

January

Cheapest flight

$98
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Boston to Chicago Midway 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
Munster
Schererville
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 $701
Business Class flights to Chicagofrom $929
Premium Economy Class flights to Chicagofrom $885
Economy Class flights to Chicagofrom $291