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.

$104 CHEAP FLIGHTS from Maine to Chicago

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

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

Sat, Oct 24 - Tue, Oct 27

6:55 am - 8:46 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

8:24 pm - 11:56 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$163JetBlue

Wed, Sep 23 - Tue, Sep 29

5:00 pm - 7:01 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

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

2h 28mnonstop

$165JetBlue

Tue, Nov 3 - Sat, Nov 7

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

2h 54mnonstop

4:40 pm - 8:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

$165Delta

Sat, Oct 24 - Mon, Oct 26

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

2h 54mnonstop

7:10 pm - 10:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

$165Delta

Fri, Jan 8 - Tue, Jan 12

6:00 am - 8:02 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

8:29 am - 12:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

$165American Airlines

Fri, Sep 11 - Mon, Sep 14

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

3h 02mnonstop

1:54 pm - 5:35 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

$165American Airlines

Wed, Oct 21 - Sun, Oct 25

8:30 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 17mnonstop

$165United Airlines

Fri, Sep 18 - Mon, Sep 21

8:31 pm - 10:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

9:40 pm - 1:10 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$165United Airlines

Thu, Oct 15 - Tue, Oct 20

10:00 pm - 11:35 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$165Southwest

Thu, Oct 22 - Mon, Oct 26

10:00 pm - 11:35 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

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

2h 25mnonstop

$165Southwest

Recent last minute flight deals from Maine to Chicago

Thu, Aug 20 - Sat, Aug 29

9:36 am - 7:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

11h 23m1 stop Atlanta Hartsfield-Jackson

5:59 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

14h 10m1 stop Orlando

$207Frontier

Sun, Aug 23 - Sat, Aug 29

9:36 am - 7:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

11h 23m1 stop Atlanta Hartsfield-Jackson

5:59 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

14h 10m1 stop Orlando

$207Frontier

Sat, Aug 22 - Sat, Sep 12

11:05 am - 12:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

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

2h 45mnonstop

$283JetBlue

Thu, Aug 20 - Sat, Sep 12

8:15 am - 10:11 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

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

2h 28mnonstop

$283JetBlue

Sat, Aug 22 - Sat, Sep 12

7:05 am - 8:40 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

9:05 am - 12:25 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$286Southwest

Sat, Aug 22 - Wed, Sep 2

7:05 am - 8:40 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

6:00 pm - 9:20 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$286Southwest

Sun, Aug 23 - Sat, Aug 29

7:30 am - 9:26 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:30 am - 10:59 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$286Delta

Fri, Aug 21 - Sat, Aug 29

8:50 pm - 10:44 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:30 am - 10:59 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$286Delta

Sat, Aug 22 - Mon, Aug 31

11:58 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

7:00 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$286American Airlines

Sat, Aug 22 - Fri, Aug 28

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

3h 06mnonstop

7:15 pm - 10:50 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$286American Airlines

Recent direct flight deals from Maine to Chicago

Thu, Oct 22 - Tue, Oct 27

5:00 pm - 7:22 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 22mnonstop

8:24 pm - 11:56 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$163JetBlue

Sat, Sep 5 - Sat, Sep 12

11:00 am - 12:54 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

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

2h 45mnonstop

$163JetBlue

Thu, Oct 15 - Tue, Oct 20

10:00 pm - 11:35 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$165Southwest

Thu, Oct 22 - Mon, Oct 26

10:00 pm - 11:35 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

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

2h 25mnonstop

$165Southwest

Thu, Sep 3 - Tue, Sep 8

7:30 am - 9:26 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:30 pm - 11:09 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$165Delta

Tue, Nov 3 - Sat, Nov 7

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

2h 54mnonstop

4:40 pm - 8:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

$165Delta

Wed, Oct 21 - Sun, Oct 25

5:54 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

6:00 am - 9:37 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

$165American Airlines

Sat, Oct 10 - Tue, Oct 13

4:48 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

5:11 pm - 8:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 48mnonstop

$165American Airlines

Sun, Sep 20 - Mon, Sep 21

7:05 am - 9:03 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

7:55 pm - 11:30 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$165United Airlines

Wed, Oct 21 - Sun, Oct 25

8:30 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 17mnonstop

$165United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$104

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly with an average 18% increase in price.

Flight from Boston to Chicago O'Hare 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Maine

First Class flights to Chicagofrom $562

Business Class flights to Chicagofrom $1,664

Premium Economy Class flights to Chicagofrom $885

Economy Class flights to Chicagofrom $291

$104 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

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maine

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight