Find cheap flights from Massachusetts to Chicago

Find cheap flights from Massachusetts to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Fri 7/31
Fri 8/7
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

Good to know

Low season

September Best time to beat the crowds with an average 8% drop in price.

High season

July Most popular time to fly with an average 6% increase in price.

Average price of a round-trip

$212 (avg. price over the last 2 weeks)

Good deal for a round-trip

$104 or less

FAQs for booking Massachusetts to Chicago flights

How does KAYAK find such low prices on flights from Massachusetts to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Chicago?

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

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

Top airlines flying from Massachusetts 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 Massachusetts to Chicago (round-trip)

Airports
Origin
Boston
$31
only
$31
Destination
Chicago
$31
only
$31
$90
only
$90
Fri, Aug 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Fri, Aug 21
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 15 days
Based on null reviews
Fri, Jul 24
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Sun, Jul 26
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 3 days
Based on null reviews
Sun, Aug 9
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 42m
Fri, Aug 14
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 26m
Trip: 6 days
Based on null reviews
Sat, Aug 1
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Mon, Aug 3
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 21m
Trip: 3 days
Based on null reviews
Thu, Jul 23
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Sun, Jul 26
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 21m
Trip: 4 days
Based on null reviews
Fri, Aug 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Fri, Aug 14
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 8 days
Based on null reviews
Thu, Sep 17
BOS
Boston Logan Airport
MDW
Chicago Midway Airport
6h 25m
Sun, Sep 20
MDW
Chicago Midway Airport
BOS
Boston Logan Airport
7h 34m
Trip: 4 days
Based on null reviews
Thu, Aug 6
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Sun, Aug 9
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 4 days
Based on null reviews
Fri, Jul 24
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 49m
Sun, Jul 26
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
4h 53m
Trip: 3 days
Based on null reviews
Fri, Aug 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Fri, Aug 21
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
4h 53m
Trip: 15 days
Based on null reviews
Wed, Aug 5
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 42m
Sat, Aug 8
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 4 days
Based on null reviews
Thu, Aug 13
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Thu, Aug 20
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
4h 53m
Trip: 8 days
Based on null reviews
Thu, Jul 23
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 42m
Fri, Jul 24
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 21m
Trip: 2 days
Based on null reviews
Mon, Jul 27
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
9h 30m
Mon, Aug 3
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 21m
Trip: 8 days
Based on null reviews
Mon, Aug 10
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
4h 40m
Sat, Aug 15
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 6 days
Based on null reviews
Fri, Jul 24
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Mon, Aug 3
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
9h 32m
Trip: 11 days
Based on null reviews
Thu, Aug 20
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
4h 40m
Sun, Aug 23
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 4 days
Based on null reviews
Tue, Aug 4
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Sat, Aug 22
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 25m
Trip: 19 days
Based on null reviews
Tue, Aug 4
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 47m
Sat, Aug 22
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
9h 00m
Trip: 19 days
Based on null reviews
Thu, Sep 3
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 45m
Thu, Sep 17
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 20m
Trip: 15 days
Based on null reviews

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

Airports
Origin
Boston
$16
only
$16
Destination
Chicago
$16
only
$16
$45
only
$45
Sat, Aug 1
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Based on null reviews
Sun, Jul 26
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 49m
Based on null reviews
Wed, Jul 29
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 50m
Based on null reviews
Fri, Aug 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Based on null reviews
Wed, Jul 29
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
8h 59m
Based on null reviews
Fri, Aug 21
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Based on null reviews
Sun, Sep 13
BOS
Boston Logan Airport
MDW
Chicago Midway Airport
5h 26m
Based on null reviews
Sun, Jul 26
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
9h 30m
Based on null reviews
Fri, Sep 4
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
Based on null reviews
Fri, Sep 4
BOS
Boston Logan Airport
MDW
Chicago Midway Airport
6h 28m
Based on null reviews
Fri, Jul 31
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
9h 43m
Based on null reviews
Thu, Jul 23
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 52m
Based on null reviews
Mon, Aug 17
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
7h 39m
Based on null reviews
Thu, Jul 30
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
19h 58m
Based on null reviews
Thu, Jul 23
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 50m
Based on null reviews
Wed, Aug 12
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
24h 06m
Based on null reviews
Sun, Jul 26
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
9h 30m
Based on null reviews
Thu, Jul 23
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
5h 34m
Based on null reviews
Mon, Jul 27
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
21h 41m
Based on null reviews
Fri, Aug 28
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 57m
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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