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Cheap flights from Maine to Chicago from $34

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 8/28. 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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Cheap round-trip flights

Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
$67Southwest
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Thu, Sep 4 - Mon, Sep 8
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
$77Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$80JetBlue
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Thu, Sep 4 - Tue, Sep 9
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$81JetBlue
Find Deal
Sat, Sep 20 - Sat, Sep 27
American Airlines Logo
2:45 pm - 4:49 pmBOS-ORD
3h 04mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$94American Airlines
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Thu, Sep 4 - Thu, Sep 11
American Airlines Logo
7:19 pm - 9:25 pmBOS-ORD
3h 06mnonstop
American Airlines Logo
3:08 pm - 6:29 pmORD-BOS
2h 21mnonstop
$98American Airlines
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Fri, Nov 14 - Mon, Nov 17
United Airlines Logo
6:16 pm - 8:10 pmBOS-ORD
2h 54mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$108United Airlines
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Wed, Aug 20 - Sun, Aug 24
Spirit Airlines Logo
6:05 am - 7:07 pmBOS-ORD
14h 02m1 stop
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
$112Spirit Airlines
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Wed, Sep 3 - Wed, Sep 10
United Airlines Logo
8:47 pm - 10:35 pmBOS-ORD
2h 48mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$113United Airlines
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Fri, Oct 17 - Sun, Oct 19
Spirit Airlines Logo
3:37 pm - 10:22 pmBOS-ORD
7h 45m1 stop
Spirit Airlines Logo
11:36 am - 11:49 pmORD-BOS
11h 13m1 stop
$121Spirit Airlines
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Tue, Aug 26 - Wed, Sep 3

Spirit Airlines flights from Maine to Chicago

Our best Spirit Airlines deals on Maine to Chicago flight tickets
Spirit Airlines
Sep 3
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
Sep 10
ORD11:57 amChicago O'Hare Intl
11h 00m
1 stop
BOS11:57 pmBoston Logan Intl
$112
Find similar
Spirit Airlines
Aug 26
BOS3:37 pmBoston Logan Intl
7h 45m
1 stop
ORD10:22 pmChicago O'Hare Intl
Sep 3
ORD11:36 amChicago O'Hare Intl
11h 13m
1 stop
BOS11:49 pmBoston Logan Intl
$121
Find similar
Spirit Airlines
Aug 27
BOS3:37 pmBoston Logan Intl
7h 45m
1 stop
ORD10:22 pmChicago O'Hare Intl
Sep 2
ORD8:12 pmChicago O'Hare Intl
14h 06m
1 stop
BOS11:18 amBoston Logan Intl
$125
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American Airlines flights from Maine to Chicago

Our best American Airlines deals on Maine to Chicago flight tickets
American Airlines
Sep 4
BOS2:45 pmBoston Logan Intl
3h 04m
ORD4:49 pmChicago O'Hare Intl
Sep 11
ORD6:05 amChicago O'Hare Intl
2h 27m
BOS9:32 amBoston Logan Intl
$94
Find similar
American Airlines
Nov 14
BOS7:19 pmBoston Logan Intl
3h 06m
ORD9:25 pmChicago O'Hare Intl
Nov 17
ORD3:08 pmChicago O'Hare Intl
2h 21m
BOS6:29 pmBoston Logan Intl
$98
Find similar
American Airlines
Sep 21
BOS5:00 amBoston Logan Intl
2h 51m
ORD6:51 amChicago O'Hare Intl
Sep 28
ORD6:05 amChicago O'Hare Intl
2h 27m
BOS9:32 amBoston Logan Intl
$100
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momondo Fare Finder

 
Customize your flight search to find flights from Maine to Chicago 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 7, 2025.
Use the filters below to find and compare flights from Maine to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Mon 9/8

6:45 pm-10:05 pm

Nonstop2h 20m

$67

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Mon 9/8

2:35 pm-11:00 pm

1 stop7h 25m

$77

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 9/9

9:51 am-1:20 pm

Nonstop2h 29m

$80

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/20

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/27

9:51 am-1:20 pm

Nonstop2h 29m

$81

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

2:45 pm-4:49 pm

Nonstop3h 04m

Chicago O'Hare Intl

Thu 9/11

6:05 am-9:32 am

Nonstop2h 27m

$94

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/14

7:19 pm-9:25 pm

Nonstop3h 06m

Chicago O'Hare Intl

Mon 11/17

3:08 pm-6:29 pm

Nonstop2h 21m

$98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 8/20

6:16 pm-8:10 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 8/24

6:30 am-9:56 am

Nonstop2h 26m

$108

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/3

6:05 am-7:07 pm

1 stop14h 02m

Chicago O'Hare Intl

Wed 9/10

11:57 am-11:57 pm

1 stop11h 00m

$112

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/17

8:47 pm-10:35 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$113

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/26

3:37 pm-10:22 pm

1 stop7h 45m

Chicago O'Hare Intl

Wed 9/3

11:36 am-11:49 pm

1 stop11h 13m

$121

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

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?

The month of September is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $282. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Maine to Chicago during May average around $304.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $447. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Maine to Chicago for around $631.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maine to Chicago during this time can be as low as $434. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $496.

What is the cheapest Maine to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $376 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Maine for as low as $228 on momondo.

What cabin class options are available on Maine to Chicago flights?

There are 4 cabin classes available to choose from on Maine to Chicago 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 flights?

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

Cheap Maine to Chicago flight deals and tips

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

Best Price Found

$34

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Maine in the past 72 hours is $34. The best round-trip flight deal from Maine to Chicago found on momondo in the last 72 hours is $67.
The fastest flight from Maine to Chicago takes 2h 30m
Direct flights go from Maine to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • When did momondo last update prices for flights from Maine to Chicago?

    Prices for flights from Maine to Chicago were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Maine to Chicago.

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

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Maine to Chicago

Compare and see reviews for airlines that fly from Maine to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $124Free CancellationRating
8.0
7,985 reviews
Search Delta flights
American AirlinesPriceFrom $199Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $231Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,247 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Maine to Chicago. momondo saves you time and could save you money on your trip.

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?

momondo provides multiple filters to help you find the best flight to Chicago from Maine. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Maine and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport