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Cheap flights from Maine to Chicago from $103

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maine to Chicago departing on 10/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
Sat, Sep 26 - Sat, Oct 3
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
Thu, Oct 1 - Mon, Oct 5
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
$163JetBlue
Wed, Oct 21 - Sat, Oct 24
JetBlue Logo
11:00 am - 12:54 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
JetBlue Logo
8:24 pm - 12:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 45mnonstop
$163JetBlue
Sat, Sep 5 - Sat, Sep 12
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
4:40 pm - 8:21 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 41mnonstop
$165Delta
Tue, Nov 3 - Sat, Nov 7
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
3:05 pm - 6:44 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 39mnonstop
$165Delta
Tue, Oct 13 - Wed, Oct 14
American Airlines Logo
7:00 am - 9:05 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 05mnonstop
American Airlines Logo
6:00 am - 9:37 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 37mnonstop
$165American Airlines
Mon, Oct 12 - Sun, Oct 18
American Airlines Logo
6:00 am - 8:10 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 10mnonstop
American Airlines Logo
6:50 am - 10:29 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 39mnonstop
$165American Airlines
Mon, Sep 14 - Sun, Sep 20
United Airlines Logo
7:55 am - 9:51 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 56mnonstop
United Airlines Logo
6:10 am - 9:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 23mnonstop
$165United Airlines
Tue, Sep 29 - Wed, Sep 30
United Airlines Logo
7:05 am - 9:04 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
7:55 pm - 11:30 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
$165United Airlines
Mon, Sep 7 - Mon, Sep 14

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Delta flights from Maine to Chicago O'Hare Intl Airport

Our best Delta deals on Maine to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 3
BOS7:30 amBoston Logan Intl
2h 56m
ORD9:26 amChicago O'Hare Intl
Sep 5
ORD7:30 amChicago O'Hare Intl
2h 29m
BOS10:59 amBoston Logan Intl
$165
Delta
Sep 3
BOS7:30 amBoston Logan Intl
2h 56m
ORD9:26 amChicago O'Hare Intl
Sep 9
ORD2:29 pmChicago O'Hare Intl
6h 57m
1 stop
BOS10:26 pmBoston Logan Intl
$175
Delta
Oct 22
BOS5:39 amBoston Logan Intl
5h 51m
1 stop
ORD10:30 amChicago O'Hare Intl
Oct 27
ORD11:30 amChicago O'Hare Intl
5h 58m
1 stop
BOS6:28 pmBoston Logan Intl
$185

Frontier flights from Maine to Chicago O'Hare Intl Airport

Our best Frontier deals on Maine to Chicago O'Hare Intl Airport flight tickets
Frontier
Sep 26
BOS12:54 pmBoston Logan Intl
6h 29m
1 stop
ORD6:23 pmChicago O'Hare Intl
Oct 3
ORD8:05 amChicago O'Hare Intl
7h 24m
1 stop
BOS4:29 pmBoston Logan Intl
$162
Frontier
Aug 31
BOS12:45 pmBoston Logan Intl
8h 14m
1 stop
ORD7:59 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
12h 25m
1 stop
BOS9:09 amBoston Logan Intl
$168
Frontier
Oct 3
BOS12:54 pmBoston Logan Intl
6h 29m
1 stop
ORD6:23 pmChicago O'Hare Intl
Oct 4
ORD6:00 amChicago O'Hare Intl
2h 39m
BOS9:39 amBoston Logan Intl
$173

momondo Fare Finder

 
Customize your flight search to find flights from Maine to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 15, 2026.
Use the filters below to find and compare flights from Maine to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 9/26

12:54 pm-6:23 pm

1 stop6h 29m

Chicago O'Hare Intl

Sat 10/3

8:05 am-4:29 pm

1 stop7h 24m

$162

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 10/1

11:17 am-10:59 pm

1 stop12h 42m

Chicago O'Hare Intl

Mon 10/5

8:24 pm-12:23 am

Nonstop2h 59m

$162

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 10/21

6:55 am-8:46 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 10/24

8:24 pm-11:58 pm

Nonstop2h 34m

$163

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 9/5

11:00 am-12:54 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sat 9/12

8:24 pm-12:09 am

Nonstop2h 45m

$163

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 11/3

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Sat 11/7

4:40 pm-8:21 pm

Nonstop2h 41m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/13

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Wed 10/14

3:05 pm-6:44 pm

Nonstop2h 39m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 10/12

7:00 am-9:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sun 10/18

6:00 am-9:37 am

Nonstop2h 37m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 9/14

6:00 am-8:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Sun 9/20

6:50 am-10:29 am

Nonstop2h 39m

$165
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 9/29

7:55 am-9:51 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/30

6:10 am-9:33 am

Nonstop2h 23m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 9/7

7:05 am-9:04 am

Nonstop2h 59m

Chicago O'Hare Intl

Mon 9/14

7:55 pm-11:30 pm

Nonstop2h 35m

$165

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Maine to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Maine averaging around $326.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $434. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $617.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Maine at noon is the least expensive time of day to depart. momondo users have found prices as low as $388 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $498. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Maine to Chicago O'Hare Intl flight route?

Fly from Portland to Chicago O'Hare Intl for the best Maine - Chicago O'Hare Intl flight prices

How far in advance should I book a flight from Maine to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $364 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Maine for as low as $282 on momondo.

What cabin class options are available on Maine to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Maine to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Maine to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Maine to Chicago O'Hare Intl Airport.

Cheap Maine to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maine to Chicago O'Hare Intl Airport

Best Price Found

$236

Fastest flight time

2h 48m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Maine in the past 72 hours is $236. The best round-trip flight deal from Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $383.
The fastest flight from Maine to Chicago O'Hare Intl Airport takes 2h 48m
Direct flights go from Maine to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Maine to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Maine to Chicago O'Hare Intl Airport?

    Prices for flights from Maine to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Maine to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Maine to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Maine to Chicago O'Hare Intl Airport?

Best airlines flying from Maine to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Maine to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,941 reviews
Search American Airlines flights
United AirlinesPriceFrom $229Free CancellationRating
7.4
10,111 reviews
Search United Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.8
8,508 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Gurnee
Rosemont
Oak Brook
Orland Park
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Racine
Aurora
Janesville
Elgin
South Holland
Evanston

Why use momondo?

Why should I use momondo to find a flight deal from Maine to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Maine to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Maine to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Maine which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Maine to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Maine.

I’m not ready to book a flight from Maine to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Maine to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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