$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 8/12. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
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

Fri, Aug 21 - Fri, Aug 28
Southwest Logo
6:40 pm - 8:20 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
6:30 pm - 9:50 pm
MDW
-
BOS
2h 20mnonstop
$165Southwest
Sun, Aug 2 - Fri, Aug 28
JetBlue Logo
8:07 am - 10:05 am
BOS
-
ORD
2h 58mnonstop
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
$165JetBlue
Tue, Jul 28 - Thu, Aug 6
United Airlines Logo
9:50 am - 11:43 am
BOS
-
ORD
2h 53mnonstop
United Airlines Logo
9:41 pm - 1:14 am
ORD
-
BOS
2h 33mnonstop
$166United Airlines
Sat, Jul 25 - Tue, Jul 28
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
9:15 am - 12:57 pm
ORD
-
BOS
2h 42mnonstop
$170United Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
12:45 pm - 3:00 pm
BGR
-
ORD
3h 15mnonstop
American Airlines Logo
1:10 pm - 5:00 pm
ORD
-
BGR
2h 50mnonstop
$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
Wed, Aug 19 - Wed, Aug 26
Delta Logo
12:05 pm - 7:12 pm
BGR
-
ORD
8h 07m
1 stop
Delta Logo
1:50 pm - 11:40 pm
ORD
-
BGR
8h 50m
2 stops
$286Delta
Wed, Aug 19 - Wed, Aug 26
Delta Logo
5:20 am - 4:15 pm
BGR
-
MDW
11h 55m
2 stops
Delta Logo
10:54 am - 11:40 pm
MDW
-
BGR
11h 46m
2 stops
$291Delta
Fri, Aug 7 - Mon, Aug 10
Multiple Airlines Logo
12:29 pm - 8:25 am
BOS
-
RFD
20h 56m
1 stop
Multiple Airlines Logo
6:26 pm - 9:09 am
RFD
-
BOS
13h 43m
1 stop
$292Multiple Airlines
Fri, Aug 7 - Sun, Aug 16
Multiple Airlines Logo
12:29 pm - 8:25 am
BOS
-
RFD
20h 56m
1 stop
Multiple Airlines Logo
11:37 am - 7:46 am
RFD
-
BOS
19h 09m
2 stops
$340Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$98
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 $1,203
Business Class flights to Chicagofrom $929
Premium Economy Class flights to Chicagofrom $885
Economy Class flights to Chicagofrom $289