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Cheap flights from Massachusetts to Chicago from $98

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Chicago departing on 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:45 pm - 8:08 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
$166Frontier
Wed, Aug 26 - Sat, Sep 5
Frontier Logo
12:45 pm - 8:08 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
$166Frontier
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
6:55 am - 8:46 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
JetBlue Logo
8:24 pm - 11:58 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 34mnonstop
$201JetBlue
Tue, Oct 20 - Sat, Oct 24
JetBlue Logo
5:00 pm - 7:01 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 01mnonstop
JetBlue Logo
8:24 pm - 12:23 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 59mnonstop
$202JetBlue
Sat, Oct 3 - Tue, Oct 6
Delta Logo
6:00 pm - 7:59 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
Delta Logo
3:05 pm - 6:44 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 39mnonstop
$207Delta
Sat, Oct 3 - Tue, Oct 6
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
7:10 pm - 10:53 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 43mnonstop
$207Delta
Wed, Oct 21 - Wed, Oct 28
American Airlines Logo
1:34 pm - 3:35 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 01mnonstop
American Airlines Logo
6:50 am - 10:29 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 39mnonstop
$217American Airlines
Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
6:00 pm - 8:12 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 12mnonstop
American Airlines Logo
7:00 am - 10:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
$217American Airlines
Sat, Oct 10 - Tue, Oct 13
United Airlines Logo
8:00 am - 9:56 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 56mnonstop
United Airlines Logo
9:24 pm - 12:54 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 30mnonstop
$217United Airlines
Wed, Oct 21 - Sat, Oct 24
United Airlines Logo
12:45 pm - 2:37 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
United Airlines Logo
6:24 pm - 9:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
$217United Airlines
Tue, Sep 29 - Sat, Oct 3

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Frontier flights from Massachusetts to Chicago O'Hare Intl Airport

Our best Frontier deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
Frontier
Aug 31
BOS10:04 amBoston Logan Intl
14h 04m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
12h 25m
1 stop
BOS9:09 amBoston Logan Intl
$166
Frontier
Aug 29
BOS12:45 pmBoston Logan Intl
8h 23m
1 stop
ORD8:08 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
12h 25m
1 stop
BOS9:09 amBoston Logan Intl
$167
Frontier
Sep 2
BOS12:45 pmBoston Logan Intl
8h 23m
1 stop
ORD8:08 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
12h 25m
1 stop
BOS9:09 amBoston Logan Intl
$168

Delta flights from Massachusetts to Chicago O'Hare Intl Airport

Our best Delta deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 22
BOS7:30 amBoston Logan Intl
2h 54m
ORD9:24 amChicago O'Hare Intl
Sep 26
ORD11:30 amChicago O'Hare Intl
2h 45m
BOS3:15 pmBoston Logan Intl
$217
Delta
Aug 17
BOS8:50 pmBoston Logan Intl
2h 54m
ORD10:44 pmChicago O'Hare Intl
Aug 21
ORD10:30 amChicago O'Hare Intl
2h 29m
BOS1:59 pmBoston Logan Intl
$245
Delta
Sep 11
ORH4:20 pmWorcester
6h 58m
1 stop
ORD10:18 pmChicago O'Hare Intl
Sep 21
ORD9:30 amChicago O'Hare Intl
5h 07m
1 stop
ORH3:37 pmWorcester
$255

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Chicago O'Hare Intl Airport 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 5, 2026.
Use the filters below to find and compare flights from Massachusetts to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 8/26

12:45 pm-8:08 pm

1 stop8h 23m

Chicago O'Hare Intl

Sat 9/5

7:44 pm-9:09 am

1 stop12h 25m

$166

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 8/29

12:45 pm-8:08 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 9/2

7:44 pm-9:09 am

1 stop12h 25m

$166
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/20

6:55 am-8:46 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 10/24

8:24 pm-11:58 pm

Nonstop2h 34m

$201

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 10/3

5:00 pm-7:01 pm

Nonstop3h 01m

Chicago O'Hare Intl

Tue 10/6

8:24 pm-12:23 am

Nonstop2h 59m

$202

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 10/3

6:00 pm-7:59 pm

Nonstop2h 59m

Chicago O'Hare Intl

Tue 10/6

3:05 pm-6:44 pm

Nonstop2h 39m

$207

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 10/21

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Wed 10/28

7:10 pm-10:53 pm

Nonstop2h 43m

$207

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 9/16

1:34 pm-3:35 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sat 9/19

6:50 am-10:29 am

Nonstop2h 39m

$217

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 10/10

6:00 pm-8:12 pm

Nonstop3h 12m

Chicago O'Hare Intl

Tue 10/13

7:00 am-10:33 am

Nonstop2h 33m

$217

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 10/21

8:00 am-9:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 10/24

9:24 pm-12:54 am

Nonstop2h 30m

$217

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 9/29

12:45 pm-2:37 pm

Nonstop2h 52m

Chicago O'Hare Intl

Sat 10/3

6:24 pm-9:59 pm

Nonstop2h 35m

$217

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 Massachusetts to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $221.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $311. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $409.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $272 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $387. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Massachusetts to Chicago O'Hare Intl flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Massachusetts - Chicago O'Hare Intl flight prices

How far in advance should I book a flight from Massachusetts to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $252 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Massachusetts for as low as $223 on momondo.

What cabin class options are available on Massachusetts to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Massachusetts to Chicago O'Hare Intl Airport 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 Massachusetts to Chicago O'Hare Intl Airport flights?

You could potentially save up to 2% on your flight if you consider stops on a Massachusetts to Chicago O'Hare Intl Airport flight.

Cheap Massachusetts to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago O'Hare Intl Airport

Best Price Found

$163

Fastest flight time

2h 23m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Massachusetts in the past 72 hours is $163. The best round-trip flight deal from Massachusetts to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $240.
The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 23m
Direct flights go from Massachusetts to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Massachusetts to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Massachusetts to Chicago O'Hare Intl Airport?

    Prices for flights from Massachusetts to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Massachusetts to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Massachusetts to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Massachusetts to Chicago O'Hare Intl Airport?

Best airlines flying from Massachusetts to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Massachusetts to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $69Free CancellationRating
7.1
3,023 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.8
8,487 reviews
Search Delta flights
United AirlinesPriceFrom $126Free CancellationRating
7.4
10,060 reviews
Search United Airlines flights
American AirlinesPriceFrom $137Free CancellationRating
7.1
11,849 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Rosemont
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Hammond
Racine
Aurora
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South Holland
Evanston

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Massachusetts to Chicago for you.

Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?

All flight searches from Massachusetts to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Massachusetts to Chicago?

Once all potential Massachusetts to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Massachusetts 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 Massachusetts and alert you when they change.

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