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Cheap flights from Maine to Illinois from $82

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 Illinois departing on 6/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Maine to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 10:02 pm
BOS
-
MDW
17h 02m
1 stop
Frontier Logo
6:00 am - 1:27 am
MDW
-
BOS
18h 27m
1 stop
$169Frontier
Wed, Jun 3 - Wed, Jun 10
Frontier Logo
9:12 am - 7:55 am
BOS
-
ORD
23h 43m
1 stop
Frontier Logo
6:55 am - 1:27 am
ORD
-
BOS
17h 32m
1 stop
$169Frontier
Tue, Jun 2 - Tue, Jun 9
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
6:15 am - 9:39 am
ORD
-
BOS
2h 24mnonstop
$172United Airlines
Sat, May 30 - Sun, May 31
Southwest Logo
7:30 am - 9:10 am
BOS
-
MDW
2h 40mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$172Southwest
Thu, Jun 4 - Tue, Jun 9
American Airlines Logo
7:46 pm - 10:00 pm
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:04 am - 9:30 am
ORD
-
BOS
2h 26mnonstop
$173American Airlines
Wed, Jun 17 - Sat, Jun 20
United Airlines Logo
5:05 pm - 7:05 pm
BOS
-
ORD
3h 00mnonstop
United Airlines Logo
6:20 pm - 9:56 pm
ORD
-
BOS
2h 36mnonstop
$177United Airlines
Sat, May 23 - Wed, May 27
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:20 pm - 11:30 pm
MDW
-
BOS
5h 10m
1 stop
$177Southwest
Tue, Jun 30 - Tue, Jul 7
JetBlue Logo
5:20 pm - 7:25 pm
BOS
-
ORD
3h 05mnonstop
JetBlue Logo
10:56 am - 2:23 pm
ORD
-
BOS
2h 27mnonstop
$180JetBlue
Fri, Jul 24 - Tue, Jul 28
JetBlue Logo
8:10 am - 10:06 am
BOS
-
ORD
2h 56mnonstop
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
$181JetBlue
Tue, Jun 16 - Fri, Jun 19
American Airlines Logo
5:05 am - 7:02 am
BOS
-
ORD
2h 57mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$184American Airlines
Sat, May 30 - Sun, May 31

Delta flights from Maine to Illinois

Our best Delta deals on Maine to Illinois flight tickets
Delta
May 30
BOS5:30 pmBoston Logan Intl
3h 03m
ORD7:33 pmChicago O'Hare Intl
May 31
ORD7:00 amChicago O'Hare Intl
2h 35m
BOS10:35 amBoston Logan Intl
$183
Delta
May 30
BOS5:30 pmBoston Logan Intl
3h 03m
ORD7:33 pmChicago O'Hare Intl
May 31
ORD7:00 amChicago O'Hare Intl
2h 35m
BOS10:35 amBoston Logan Intl
$186
Delta
May 20
BOS4:15 pmBoston Logan Intl
3h 00m
ORD6:15 pmChicago O'Hare Intl
May 30
ORD4:30 pmChicago O'Hare Intl
2h 36m
BOS8:06 pmBoston Logan Intl
$191

American Airlines flights from Maine to Illinois

Our best American Airlines deals on Maine to Illinois flight tickets
American Airlines
Jun 17
BOS7:46 pmBoston Logan Intl
3h 14m
ORD10:00 pmChicago O'Hare Intl
Jun 20
ORD6:04 amChicago O'Hare Intl
2h 26m
BOS9:30 amBoston Logan Intl
$173
American Airlines
May 30
BOS5:05 amBoston Logan Intl
2h 57m
ORD7:02 amChicago O'Hare Intl
May 31
ORD6:00 amChicago O'Hare Intl
2h 27m
BOS9:27 amBoston Logan Intl
$184
American Airlines
May 30
BOS5:05 amBoston Logan Intl
2h 57m
ORD7:02 amChicago O'Hare Intl
May 31
ORD6:00 amChicago O'Hare Intl
2h 27m
BOS9:27 amBoston Logan Intl
$188

momondo Fare Finder

 
Customize your flight search to find flights from Maine to Illinois 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 May 10, 2026.
Use the filters below to find and compare flights from Maine to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 6/3

6:00 am-10:02 pm

1 stop17h 02m

Chicago Midway

Wed 6/10

6:00 am-1:27 am

1 stop18h 27m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/2

9:12 am-7:55 am

1 stop23h 43m

Chicago O'Hare Intl

Tue 6/9

6:55 am-1:27 am

1 stop17h 32m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 5/31

6:15 am-9:39 am

Nonstop2h 24m

$172
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 6/4

7:30 am-9:10 am

Nonstop2h 40m

Chicago Midway

Tue 6/9

7:40 am-10:55 am

Nonstop2h 15m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/17

7:46 pm-10:00 pm

Nonstop3h 14m

Chicago O'Hare Intl

Sat 6/20

6:04 am-9:30 am

Nonstop2h 26m

$173

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/23

5:05 pm-7:05 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 5/27

6:20 pm-9:56 pm

Nonstop2h 36m

$177

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 6/30

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Tue 7/7

5:20 pm-11:30 pm

1 stop5h 10m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/24

5:20 pm-7:25 pm

Nonstop3h 05m

Chicago O'Hare Intl

Tue 7/28

10:56 am-2:23 pm

Nonstop2h 27m

$180

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/16

8:10 am-10:06 am

Nonstop2h 56m

Chicago O'Hare Intl

Fri 6/19

8:20 pm-11:51 pm

Nonstop2h 31m

$181

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

5:05 am-7:02 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 5/31

6:00 am-9:27 am

Nonstop2h 27m

$184

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 Illinois from

How to get the cheapest flight ticket from Maine to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Maine is in May. Flight prices, which tend to average around $102, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of May, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $130.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Maine to Illinois is on a Wednesday when prices can be found for as low as $428. Flights from Maine to Illinois on a Sunday will generally be more expensive and average around $604. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Maine to Illinois during this time can be as low as $393. Flights in the morning are often more expensive with an average ticket price of $473.

What is the cheapest Maine to Illinois flight route?

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

How far in advance should I book a flight from Maine to Illinois?

You are more likely to see cheaper flights to Illinois from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $343 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Maine for as low as $243 on momondo.

Can stopping save me money on Maine to Illinois flights?

No. A direct flight is the cheapest option for a flight between Maine to Illinois.

Cheap Maine to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maine to Illinois

Best Price Found

$187

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Maine in the past 72 hours is $187. The best round-trip flight deal from Maine to Illinois found on momondo in the last 72 hours is $384.
The fastest flight from Maine to Illinois takes 2h 30m
Direct flights go from Maine to Illinois every day.
There are 98 airports in Illinois. From Maine there are direct flights to Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Maine to Illinois

  • When did momondo last update prices for flights from Maine to Illinois?

    Prices for flights from Maine to Illinois are updated daily.

  • How many operators does momondo search for flights from Maine to Illinois?

  • How old do you have to be to fly from Maine to Illinois?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Maine to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Maine to Illinois?

Best airlines flying from Maine to Illinois

Compare and see reviews for airlines that fly from Maine to Illinois with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights
United AirlinesPriceFrom $227Free CancellationRating
7.4
9,694 reviews
Search United Airlines flights
SouthwestPriceFrom $267Free CancellationRating
8.0
4,304 reviews
Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Maine to Illinois for you.

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

momondo does allow users to show only those flights to Illinois 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 Illinois?

Once you have performed a search for Maine to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Maine to Illinois flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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