Find cheap flights from Maine to Chicago

Find cheap flights from Maine to Chicago

Round-trip
Economy
Washington (WAS)
Chicago All airports
Mon 8/3
Mon 8/10
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

Good to know

Low season

January Best time to beat the crowds with an average 2% drop in price.

High season

May Most popular time to fly with an average 0% increase in price.

Average price of a round-trip

$364 (avg. price over the last 2 weeks)

Good deal for a round-trip

$239 or less

FAQs for booking Maine to Chicago flights

How does KAYAK find such low prices 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?

What is the Hacker Fare option on flights from Maine to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maine to Chicago?

Top airlines flying from Maine to Chicago

Scores according to KAYAK customer reviews

8.2
JetBlue
Overall score based on 19,204 reviews
8.3
Boarding
8.3
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews
Read more about JetBlue

Book cheap flights from Maine to Chicago (round-trip)

Airports
Origin
Bangor
$247
only
$247
Portland
$197
only
$197
Rockland
$420
only
$420
Destination
Chicago
$197
only
$197
$417
only
$417
Fri, Aug 21
PWM
Portland Airport
ORD
Chicago O'Hare Airport
2h 40m
Wed, Aug 26
ORD
Chicago O'Hare Airport
PWM
Portland Airport
2h 27m
Trip: 6 days
Based on null reviews
Sun, Aug 2
PWM
Portland Airport
ORD
Chicago O'Hare Airport
5h 44m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 02m
Trip: 14 days
Based on null reviews
Fri, Aug 21
PWM
Portland Airport
ORD
Chicago O'Hare Airport
7h 13m
Mon, Aug 24
ORD
Chicago O'Hare Airport
PWM
Portland Airport
2h 27m
Trip: 4 days
Based on null reviews
Thu, Jul 30
BGR
Bangor
MDW
Chicago Midway Airport
31h 05m
Sun, Aug 16
MDW
Chicago Midway Airport
BGR
Bangor
30h 27m
Trip: 18 days
Based on null reviews
Wed, Oct 14
RKD
Rockland Knox County Regional
ORD
Chicago O'Hare Airport
6h 37m
Wed, Oct 21
ORD
Chicago O'Hare Airport
RKD
Rockland Knox County Regional
5h 17m
Trip: 8 days
Based on null reviews
Wed, Aug 5
PWM
Portland Airport
ORD
Chicago O'Hare Airport
5h 44m
Fri, Aug 14
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 56m
Trip: 10 days
Based on null reviews
Sat, Aug 1
PWM
Portland Airport
ORD
Chicago O'Hare Airport
2h 40m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PWM
Portland Airport
8h 43m
Trip: 15 days
Based on null reviews
Sat, Aug 1
PWM
Portland Airport
ORD
Chicago O'Hare Airport
5h 21m
Sun, Aug 2
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 56m
Trip: 2 days
Based on null reviews
Sat, Aug 15
PWM
Portland Airport
ORD
Chicago O'Hare Airport
7h 30m
Mon, Aug 17
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 02m
Trip: 3 days
Based on null reviews
Tue, Aug 4
PWM
Portland Airport
ORD
Chicago O'Hare Airport
10h 20m
Sun, Aug 16
ORD
Chicago O'Hare Airport
PWM
Portland Airport
8h 42m
Trip: 13 days
Based on null reviews
Mon, Aug 3
PWM
Portland Airport
ORD
Chicago O'Hare Airport
2h 38m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PWM
Portland Airport
2h 23m
Trip: 13 days
Based on null reviews
Tue, Aug 4
PWM
Portland Airport
ORD
Chicago O'Hare Airport
5h 44m
Mon, Aug 17
ORD
Chicago O'Hare Airport
PWM
Portland Airport
4h 20m
Trip: 14 days
Based on null reviews
Fri, Aug 7
BGR
Bangor
ORD
Chicago O'Hare Airport
13h 41m
Mon, Aug 10
ORD
Chicago O'Hare Airport
BGR
Bangor
36h 33m
Trip: 4 days
Based on null reviews
Sat, Aug 1
PWM
Portland Airport
ORD
Chicago O'Hare Airport
2h 40m
Sun, Aug 2
ORD
Chicago O'Hare Airport
PWM
Portland Airport
2h 19m
Trip: 2 days
Based on null reviews
Sun, Aug 2
PWM
Portland Airport
ORD
Chicago O'Hare Airport
20h 06m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PWM
Portland Airport
29h 46m
Trip: 14 days
Based on null reviews
Sat, Sep 12
PWM
Portland Airport
ORD
Chicago O'Hare Airport
11h 30m
Mon, Sep 14
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 43m
Trip: 3 days
Based on null reviews
Wed, Aug 5
PWM
Portland Airport
ORD
Chicago O'Hare Airport
2h 56m
Thu, Aug 6
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 56m
Trip: 2 days
Based on null reviews
Sat, Aug 1
PWM
Portland Airport
ORD
Chicago O'Hare Airport
7h 27m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PWM
Portland Airport
7h 02m
Trip: 15 days
Based on null reviews
Thu, Sep 17
BGR
Bangor
ORD
Chicago O'Hare Airport
3h 05m
Sat, Sep 26
ORD
Chicago O'Hare Airport
BGR
Bangor
13h 52m
Trip: 10 days
Based on null reviews
Sat, Aug 1
PWM
Portland Airport
ORD
Chicago O'Hare Airport
4h 25m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PWM
Portland Airport
8h 42m
Trip: 15 days
Based on null reviews

Book cheap flights from Maine to Chicago (one-way)

Airports
Origin
Augusta
$158
only
$158
Bangor
$105
only
$105
Portland
$97
only
$97
Rockland
$188
only
$188
Destination
Chicago
$97
only
$97
$156
only
$156
Sun, Aug 9
PWM
Portland Airport
ORD
Chicago O'Hare Airport
20h 11m
Based on null reviews
Sun, Aug 9
PWM
Portland Airport
ORD
Chicago O'Hare Airport
8h 01m
Based on null reviews
Mon, Aug 10
BGR
Bangor
ORD
Chicago O'Hare Airport
13h 26m
Based on null reviews
Wed, Aug 19
BGR
Bangor
MDW
Chicago Midway Airport
23h 19m
Based on null reviews
Mon, Jul 27
AUG
Augusta
ORD
Chicago O'Hare Airport
7h 32m
Based on null reviews
Sun, Aug 9
PWM
Portland Airport
ORD
Chicago O'Hare Airport
28h 30m
Based on null reviews
Thu, Aug 13
PWM
Portland Airport
ORD
Chicago O'Hare Airport
28h 46m
Based on null reviews
Thu, Aug 13
PWM
Portland Airport
ORD
Chicago O'Hare Airport
13h 32m
Based on null reviews
Sun, Aug 9
PWM
Portland Airport
ORD
Chicago O'Hare Airport
26h 36m
Based on null reviews
Tue, Aug 11
PWM
Portland Airport
ORD
Chicago O'Hare Airport
8h 01m
Based on null reviews
Wed, Aug 19
BGR
Bangor
ORD
Chicago O'Hare Airport
32h 36m
Based on null reviews
Wed, Aug 12
PWM
Portland Airport
ORD
Chicago O'Hare Airport
10h 20m
Based on null reviews
Mon, Jul 27
RKD
Rockland Knox County Regional
ORD
Chicago O'Hare Airport
5h 17m
Based on null reviews
Sun, Jul 26
PWM
Portland Airport
ORD
Chicago O'Hare Airport
4h 25m
Based on null reviews
Sun, Jul 26
PWM
Portland Airport
ORD
Chicago O'Hare Airport
20h 21m
Based on null reviews
Fri, Jul 24
BGR
Bangor
ORD
Chicago O'Hare Airport
23h 40m
Based on null reviews
Sun, Jul 26
PWM
Portland Airport
ORD
Chicago O'Hare Airport
20h 21m
Based on null reviews
Sat, Jul 25
PWM
Portland Airport
ORD
Chicago O'Hare Airport
4h 25m
Based on null reviews
Fri, Jul 24
PWM
Portland Airport
ORD
Chicago O'Hare Airport
4h 25m
Based on null reviews
Sun, Jul 26
PWM
Portland Airport
ORD
Chicago O'Hare Airport
38h 45m
Based on null reviews
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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