$97 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

Tue, Sep 1 - Sat, Sep 5
Frontier Logo
12:45 pm - 8:08 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
$166Frontier
Mon, Aug 31 - Sat, Sep 5
Frontier Logo
12:45 pm - 7:59 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 14m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
$166Frontier
Tue, Oct 20 - Sat, Oct 24
JetBlue Logo
6:55 am - 8:46 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
JetBlue Logo
8:24 pm - 11:58 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 34mnonstop
$201JetBlue
Sat, Oct 3 - Tue, Oct 6
JetBlue Logo
5:00 pm - 7:01 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 01mnonstop
JetBlue Logo
8:24 pm - 12:23 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 59mnonstop
$202JetBlue
Sat, Oct 17 - Wed, Oct 21
Southwest Logo
9:40 am - 11:15 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
7:50 am - 11:10 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$207Southwest
Sat, Sep 19 - Tue, Sep 22
Southwest Logo
8:40 am - 10:15 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:40 am - 9:55 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$207Southwest
Sat, Oct 10 - Sat, Oct 17
Delta Logo
7:40 pm - 9:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
Delta Logo
12:00 pm - 3:32 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 32mnonstop
$207Delta
Wed, Sep 9 - Sat, Sep 12
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
4:35 pm - 8:20 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 45mnonstop
$207Delta
Wed, Sep 9 - Sat, Sep 12
American Airlines Logo
7:00 am - 9:06 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 06mnonstop
American Airlines Logo
1:54 pm - 5:35 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 41mnonstop
$207American Airlines
Wed, Sep 16 - Tue, Sep 22
American Airlines Logo
11:57 am - 1:59 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 02mnonstop
American Airlines Logo
10:30 am - 2:08 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 38mnonstop
$207American Airlines
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Good to know

Low season

January

Cheapest flight

$97
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 18% 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
Chesterton
Schererville
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 $1,664
Premium Economy Class flights to Chicagofrom $885
Economy Class flights to Chicagofrom $290