$64 Find Cheap Flights from Maine to Chicago

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 1/18. 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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Everything you should know

Cheapest round-trip
$124
Typical prices: $158-$297
Multiple Airlines
Sat 1/24Tue 1/27
BOS - ORD • 1 stop
Cheapest non-stop
$125
Typical prices: $158-$291
JetBlue
Sat 1/17Tue 1/20
BOS - ORD • Non-stop
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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

Sat, Jan 24 - Tue, Jan 27
Multiple Airlines Logo
6:00 am - 10:44 pm
BOS
-
ORD
17h 44m1 stop
Multiple Airlines Logo
9:23 am - 4:19 pm
ORD
-
BOS
29h 56m1 stop
$124Multiple Airlines
Mon, Jan 12 - Sat, Jan 17
Multiple Airlines Logo
5:23 pm - 8:18 am
BOS
-
ORD
15h 55m1 stop
Multiple Airlines Logo
4:41 pm - 1:13 am
ORD
-
BOS
7h 32m1 stop
$125Multiple Airlines
Sat, Jan 31 - Mon, Feb 2
Spirit Airlines Logo
7:00 am - 7:41 pm
BOS
-
ORD
13h 41m1 stop
Spirit Airlines Logo
12:44 pm - 11:19 pm
ORD
-
BOS
9h 35m1 stop
$126Spirit Airlines
Wed, Jan 28 - Tue, Feb 3
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
$128Frontier
Wed, Jan 28 - Sun, Feb 1
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$128JetBlue
Mon, Jan 12 - Thu, Jan 15
Spirit Airlines Logo
7:00 am - 7:41 pm
BOS
-
ORD
13h 41m1 stop
Spirit Airlines Logo
5:15 am - 4:28 pm
ORD
-
BOS
10h 13m1 stop
$129Spirit Airlines
Tue, Jan 13 - Tue, Jan 20
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$130JetBlue
Thu, Jan 1 - Thu, Jan 8
Southwest Logo
5:30 am - 7:15 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$132Southwest
Mon, Feb 9 - Tue, Feb 10
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$137Southwest
Wed, Jan 21 - Mon, Jan 26
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
$145Frontier
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% 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
Chesterton
Schererville
Munster
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 $699
Business Class flights to Chicagofrom $1,986
Prem Econ Class flights to Chicagofrom $527
Economy Class flights to Chicagofrom $279