$96 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 7/28. 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

Thu, Oct 1 - Mon, Oct 5
Southwest Logo
6:45 pm - 11:05 pm
BOS
-
MDW
5h 20m
1 stop
Southwest Logo
2:50 pm - 9:20 pm
MDW
-
BOS
5h 30m
2 stops
$162Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
6:40 pm - 8:20 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
5:55 am - 1:35 pm
MDW
-
BOS
6h 40m
1 stop
$163Southwest
Fri, Aug 28 - Sun, Aug 30
JetBlue Logo
8:15 am - 10:11 am
BOS
-
ORD
2h 56mnonstop
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
$163JetBlue
Sat, Aug 15 - Sun, Aug 16
United Airlines Logo
7:05 am - 9:04 am
BOS
-
ORD
2h 59mnonstop
United Airlines Logo
9:40 pm - 1:11 am
ORD
-
BOS
2h 31mnonstop
$164United Airlines
Fri, Aug 14 - Sun, Aug 16
United Airlines Logo
7:05 am - 9:04 am
BOS
-
ORD
2h 59mnonstop
United Airlines Logo
9:40 pm - 1:11 am
ORD
-
BOS
2h 31mnonstop
$165United Airlines
Tue, Jul 28 - Wed, Aug 5
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
Delta Logo
7:30 pm - 11:00 pm
ORD
-
BOS
2h 30mnonstop
$166Delta
Thu, Aug 13 - Mon, Aug 17
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
Delta Logo
7:30 pm - 11:00 pm
ORD
-
BOS
2h 30mnonstop
$169Delta
Tue, Sep 8 - Sat, Sep 12
JetBlue Logo
5:01 am - 8:48 am
BOS
-
ORD
4h 47m
1 stop
JetBlue Logo
8:24 pm - 11:58 pm
ORD
-
BOS
2h 34mnonstop
$171JetBlue
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
6:30 am - 8:47 am
BGR
-
ORD
3h 17mnonstop
American Airlines Logo
8:45 pm - 12:36 am
ORD
-
BGR
2h 51mnonstop
$261American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
5:30 pm - 8:01 pm
BGR
-
ORD
3h 31mnonstop
American Airlines Logo
10:30 am - 5:56 pm
ORD
-
BGR
6h 26m
1 stop
$271American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 4% 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
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 $1,314
Business Class flights to Chicagofrom $929
Premium Economy Class flights to Chicagofrom $885
Economy Class flights to Chicagofrom $302