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Cheap flights from Massachusetts to Chicago from $76

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 5/4. 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
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
10:07 am - 11:13 pm
BOS
-
ORD
14h 06m
1 stop
Frontier Logo
5:30 pm - 9:12 am
ORD
-
BOS
14h 42m
1 stop
$150Frontier
mar, mag 5 - sab, mag 9
Frontier Logo
12:01 pm - 7:51 pm
BOS
-
ORD
8h 50m
1 stop
Frontier Logo
5:30 pm - 9:12 am
ORD
-
BOS
14h 42m
1 stop
$151Frontier
mer, mag 6 - ven, mag 8
Multiple Airlines Logo
12:01 pm - 7:51 pm
BOS
-
ORD
8h 50m
1 stop
Multiple Airlines Logo
7:20 am - 10:46 am
ORD
-
BOS
2h 26mnonstop
$154Multiple Airlines
mer, mag 6 - sab, mag 9
American Airlines Logo
7:40 pm - 9:50 pm
BOS
-
ORD
3h 10mnonstop
American Airlines Logo
8:56 pm - 12:25 am
ORD
-
BOS
2h 29mnonstop
$155American Airlines
dom, apr 26 - ven, mag 1
JetBlue Logo
6:47 pm - 8:53 pm
BOS
-
ORD
3h 06mnonstop
JetBlue Logo
6:00 am - 9:16 am
ORD
-
BOS
2h 16mnonstop
$156JetBlue
sab, mag 9 - dom, mag 10
Multiple Airlines Logo
5:55 am - 9:17 pm
BOS
-
ORD
16h 22m
1 stop
Multiple Airlines Logo
6:00 am - 9:12 am
ORD
-
BOS
26h 12m
1 stop
$158Multiple Airlines
gio, apr 30 - lun, mag 4
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
10:55 am - 2:26 pm
ORD
-
BOS
2h 31mnonstop
$161American Airlines
sab, mag 2 - sab, mag 9
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
9:35 am - 4:43 pm
ORD
-
ORH
6h 08m
1 stop
$202Delta
mar, mag 5 - mer, mag 6
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
9:35 am - 4:43 pm
ORD
-
ORH
6h 08m
1 stop
$207Delta
lun, mag 4 - mer, mag 6
JetBlue Logo
5:05 pm - 9:30 pm
MVY
-
ORD
5h 25m
1 stop
JetBlue Logo
9:39 am - 4:09 pm
ORD
-
MVY
5h 30m
1 stop
$399JetBlue
mer, lug 1 - mer, lug 8

JetBlue flights from Massachusetts to Chicago O'Hare Intl Airport

Our best JetBlue deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
JetBlue
May 9
BOS6:47 pmBoston Logan Intl
3h 06m
ORD8:53 pmChicago O'Hare Intl
May 10
ORD6:00 amChicago O'Hare Intl
2h 16m
BOS9:16 amBoston Logan Intl
$156
JetBlue
May 9
BOS6:47 pmBoston Logan Intl
3h 06m
ORD8:53 pmChicago O'Hare Intl
May 12
ORD9:49 amChicago O'Hare Intl
2h 31m
BOS1:20 pmBoston Logan Intl
$162
JetBlue
May 5
BOS7:35 pmBoston Logan Intl
3h 01m
ORD9:36 pmChicago O'Hare Intl
May 12
ORD9:49 amChicago O'Hare Intl
2h 31m
BOS1:20 pmBoston Logan Intl
$165

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
May 5
BOS10:07 amBoston Logan Intl
14h 06m
1 stop
ORD11:13 pmChicago O'Hare Intl
May 9
ORD5:30 pmChicago O'Hare Intl
14h 42m
1 stop
BOS9:12 amBoston Logan Intl
$150
Frontier
May 6
BOS12:01 pmBoston Logan Intl
8h 50m
1 stop
ORD7:51 pmChicago O'Hare Intl
May 8
ORD5:30 pmChicago O'Hare Intl
14h 42m
1 stop
BOS9:12 amBoston Logan Intl
$151
Frontier
May 6
BOS10:07 amBoston Logan Intl
14h 06m
1 stop
ORD11:13 pmChicago O'Hare Intl
May 9
ORD5:30 pmChicago O'Hare Intl
14h 42m
1 stop
BOS9:12 amBoston Logan Intl
$153

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 aprile 15, 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 - ORD

BOSORD

Boston Logan Intl

mar 5/5

10:07 am-11:13 pm

1 stop14h 06m

Chicago O'Hare Intl

sab 5/9

5:30 pm-9:12 am

1 stop14h 42m

$150

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mer 5/6

12:01 pm-7:51 pm

1 stop8h 50m

Chicago O'Hare Intl

ven 5/8

5:30 pm-9:12 am

1 stop14h 42m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mer 5/6

12:01 pm-7:51 pm

1 stop8h 50m

Chicago O'Hare Intl

sab 5/9

7:20 am-10:46 am

Nonstop2h 26m

$154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dom 4/26

7:40 pm-9:50 pm

Nonstop3h 10m

Chicago O'Hare Intl

ven 5/1

8:56 pm-12:25 am

Nonstop2h 29m

$155
Quickest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sab 5/9

6:47 pm-8:53 pm

Nonstop3h 06m

Chicago O'Hare Intl

dom 5/10

6:00 am-9:16 am

Nonstop2h 16m

$156

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

gio 4/30

5:55 am-9:17 pm

1 stop16h 22m

Chicago O'Hare Intl

lun 5/4

6:00 am-9:12 am

1 stop26h 12m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sab 5/2

6:30 am-8:44 am

Nonstop3h 14m

Chicago O'Hare Intl

sab 5/9

10:55 am-2:26 pm

Nonstop2h 31m

$161

WorcesterChicago

ORH - ORD

ORHORD

Worcester

mar 5/5

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

mer 5/6

9:35 am-4:43 pm

1 stop6h 08m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

lun 5/4

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

mer 5/6

9:35 am-4:43 pm

1 stop6h 08m

$207

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

mer 7/1

5:05 pm-9:30 pm

1 stop5h 25m

Chicago O'Hare Intl

mer 7/8

9:39 am-4:09 pm

1 stop5h 30m

$399

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 $207.

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 Wednesday when prices can be found for as low as $313. 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 $407.

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 $271 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 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 $248 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 $217 on momondo.

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

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

No. A direct flight is the cheapest option for a flight between Massachusetts to Chicago O'Hare Intl Airport.

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

$126

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 $126. The best round-trip flight deal from Massachusetts to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $232.
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
Spirit AirlinesPriceFrom $32Free CancellationRating
6.3
8,614 reviews
Search Spirit Airlines flights
JetBluePriceFrom $67Free CancellationRating
7.2
2,936 reviews
Search JetBlue flights
DeltaPriceFrom $85Free CancellationRating
7.9
8,404 reviews
Search Delta flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,589 reviews
Search United Airlines flights
American AirlinesPriceFrom $129Free CancellationRating
7.1
11,580 reviews
Search American Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,331 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Elgin
Tinley Park
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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ven 5/15
ven 5/22
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