$102 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 8/30. 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
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, Sep 26 - Sat, Oct 3
Frontier Logo
12:54 pm - 6:23 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 29m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:05 am - 4:29 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
7h 24m1 stop Atlanta Hartsfield-Jackson
$162Frontier
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
11:17 am - 10:59 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
12h 42m1 stop Orlando
Multiple Airlines Logo
8:24 pm - 12:23 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 59mnonstop
$162Multiple Airlines
Tue, Oct 27 - Sat, Oct 31
JetBlue Logo
11:15 am - 1:20 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 05mnonstop
JetBlue Logo
8:24 pm - 11:56 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 32mnonstop
$163JetBlue
Tue, Sep 8 - Thu, Sep 10
JetBlue Logo
8:15 am - 10:11 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 56mnonstop
JetBlue Logo
9:38 am - 1:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 28mnonstop
$163JetBlue
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
6:40 pm - 8:25 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
5:45 am - 9:00 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$165Southwest
Thu, Oct 15 - Tue, Oct 20
Southwest Logo
10:00 pm - 11:35 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
7:50 am - 11:10 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$165Southwest
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
7:05 am - 9:03 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
United Airlines Logo
6:24 pm - 9:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
$165United Airlines
Tue, Sep 1 - Wed, Sep 2
United Airlines Logo
8:05 am - 10:04 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
9:07 am - 12:50 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 43mnonstop
$165United Airlines
Sat, Oct 24 - Mon, Oct 26
American Airlines Logo
12:00 pm - 2:02 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 02mnonstop
American Airlines Logo
5:11 pm - 8:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 48mnonstop
$165American Airlines
Thu, Sep 24 - Sat, Sep 26
American Airlines Logo
4:29 pm - 6:42 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 13mnonstop
American Airlines Logo
6:45 pm - 10:27 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 42mnonstop
$165American Airlines
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Good to know

Low season

January

Cheapest flight

$102
Best time to beat the crowds with an average 10% 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