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.

$95 CHEAP FLIGHTS from Maine to Chicago

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Cheap Flights from Maine to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Maine to Chicago

Fri, Nov 6 - Mon, Nov 9

12:39 pm - 6:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 06m1 stop Atlanta Hartsfield-Jackson

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$216Multiple Airlines

Fri, Nov 6 - Sun, Nov 8

12:39 pm - 6:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 06m1 stop Atlanta Hartsfield-Jackson

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$216Multiple Airlines

Thu, Oct 29 - Thu, Nov 5

5:50 am - 7:25 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

6:45 pm - 10:05 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$216Southwest

Thu, Oct 15 - Mon, Oct 19

10:00 pm - 11:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 40mnonstop

5:30 am - 8:55 amMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

$216Southwest

Thu, Oct 8 - Tue, Oct 13

6:55 am - 11:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$217JetBlue

Thu, Oct 1 - Mon, Oct 5

7:00 am - 8:48 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 2:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

6h 29m1 stop New York John F Kennedy Intl

$217JetBlue

Tue, Nov 3 - Wed, Nov 4

7:10 pm - 9:06 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$219Delta

Mon, Nov 9 - Thu, Nov 12

8:40 pm - 10:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:05 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mnonstop

$219Delta

Mon, Jan 18 - Wed, Jan 20

6:00 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

4:30 pm - 9:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 24m1 stop Newark

$221United Airlines

Fri, Nov 13 - Sun, Nov 15

6:05 pm - 10:18 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 13m1 stop Newark

6:15 am - 9:34 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$222United Airlines

Recent last minute flight deals from Maine to Chicago

Thu, Sep 24 - Thu, Oct 1

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

8:24 pm - 12:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$246Multiple Airlines

Wed, Sep 23 - Sun, Nov 8

5:15 am - 9:58 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 43m1 stop New York John F Kennedy Intl

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$283JetBlue

Wed, Sep 23 - Tue, Nov 10

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:05 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mnonstop

$283Delta

Thu, Sep 24 - Wed, Nov 11

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:45 pm - 11:08 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$283Delta

Wed, Sep 23 - Sun, Nov 15

12:37 pm - 2:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

6:15 am - 9:34 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$283United Airlines

Wed, Sep 23 - Sun, Nov 15

5:15 am - 9:58 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 43m1 stop New York John F Kennedy Intl

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$283JetBlue

Thu, Sep 24 - Thu, Oct 1

8:33 am - 10:35 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

6:00 am - 9:39 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$296American Airlines

Thu, Sep 24 - Sun, Sep 27

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

9:38 am - 1:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$296Multiple Airlines

Tue, Sep 22 - Tue, Sep 29

6:00 am - 7:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

7:30 am - 11:01 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$336United Airlines

Tue, Sep 22 - Thu, Oct 1

5:45 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 20mnonstop

6:00 am - 9:39 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$336American Airlines

Recent direct flight deals from Maine to Chicago

Fri, Dec 11 - Tue, Dec 15

12:45 pm - 2:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:40 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$216Southwest

Thu, Dec 3 - Mon, Dec 7

7:10 am - 8:55 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:40 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$216Southwest

Tue, Nov 3 - Wed, Nov 4

7:10 pm - 9:06 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$219Delta

Mon, Nov 9 - Thu, Nov 12

8:40 pm - 10:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:05 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mnonstop

$219Delta

Thu, Oct 15 - Sun, Oct 18

6:00 am - 7:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

6:10 am - 9:33 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$222United Airlines

Mon, Oct 12 - Fri, Oct 16

6:00 am - 7:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

9:24 pm - 12:54 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$222United Airlines

Fri, Oct 16 - Mon, Oct 19

5:12 pm - 7:14 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$224JetBlue

Wed, Nov 18 - Sat, Nov 21

3:21 pm - 5:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 15mnonstop

6:00 am - 9:24 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

$225American Airlines

Fri, Oct 16 - Mon, Oct 19

5:12 pm - 7:14 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

9:38 am - 1:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$226JetBlue

Fri, Nov 6 - Mon, Nov 9

1:30 pm - 3:37 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

8:00 pm - 11:31 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$228American Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$95

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 9% increase in price.

Flight from Boston to Chicago Midway Airport

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.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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$95 Find Cheap Flights from Maine to Chicago - Compare and Save

Cheap Flights from Maine to Chicago

Recent round-trip flight deals from Maine to Chicago

Recent one-way flight deals from Maine to Chicago

Recent last minute flight deals from Maine to Chicago

Recent direct flight deals from Maine to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Maine to Chicago

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More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Maine

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