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Cheap flights from Massachusetts to Chicago from $68

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 1/30. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 5:12 pm
BOS
-
ORD
12h 12m
1 stop
Frontier Logo
6:02 pm - 1:13 am
ORD
-
BOS
6h 11m
1 stop
$128Frontier
Tue, Feb 10 - Wed, Feb 11
Multiple Airlines Logo
6:00 am - 1:58 pm
BOS
-
ORD
8h 58m
1 stop
Multiple Airlines Logo
10:48 am - 11:19 pm
ORD
-
BOS
11h 31m
1 stop
$131Multiple Airlines
Tue, Feb 3 - Wed, Feb 4
Spirit Airlines Logo
5:53 pm - 8:18 am
BOS
-
ORD
15h 25m
1 stop
Spirit Airlines Logo
10:48 am - 11:19 pm
ORD
-
BOS
11h 31m
1 stop
$133Spirit Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
11:31 am - 11:47 pm
BOS
-
ORD
13h 16m
1 stop
Multiple Airlines Logo
4:42 pm - 1:13 am
ORD
-
BOS
7h 31m
1 stop
$134Multiple Airlines
Wed, Feb 18 - Mon, Mar 2
United Airlines Logo
12:45 pm - 2:49 pm
BOS
-
ORD
3h 04mnonstop
United Airlines Logo
7:30 am - 10:53 am
ORD
-
BOS
2h 23mnonstop
$135United Airlines
Fri, Jan 30 - Tue, Feb 3
Spirit Airlines Logo
5:23 pm - 11:22 am
BOS
-
ORD
18h 59m
1 stop
Spirit Airlines Logo
7:20 am - 11:57 pm
ORD
-
BOS
15h 37m
1 stop
$136Spirit Airlines
Mon, Feb 2 - Tue, Feb 10
Delta Logo
3:50 pm - 5:53 pm
BOS
-
ORD
3h 03mnonstop
Delta Logo
10:11 am - 1:35 pm
ORD
-
BOS
2h 24mnonstop
$137Delta
Fri, Feb 20 - Wed, Feb 25
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$138JetBlue
Fri, Jan 30 - Tue, Feb 10
Delta Logo
4:30 pm - 10:05 pm
ORH
-
ORD
6h 35m
1 stop
Delta Logo
9:35 am - 3:33 pm
ORD
-
ORH
4h 58m
1 stop
$213Delta
Tue, Feb 17 - Wed, Feb 18
United Airlines Logo
10:05 am - 11:52 am
ALB
-
ORD
2h 47mnonstop
United Airlines Logo
7:40 pm - 10:48 pm
ORD
-
ALB
2h 08mnonstop
$269United Airlines
Wed, Feb 11 - Sat, Feb 14

United Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best United Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
United Airlines
Jan 30
BOS12:45 pmBoston Logan Intl
3h 04m
ORD2:49 pmChicago O'Hare Intl
Feb 3
ORD7:30 amChicago O'Hare Intl
2h 23m
BOS10:53 amBoston Logan Intl
$135
United Airlines
Jan 15
BOS9:30 amBoston Logan Intl
3h 04m
ORD11:34 amChicago O'Hare Intl
Jan 17
ORD6:05 pmChicago O'Hare Intl
2h 33m
BOS9:38 pmBoston Logan Intl
$158
United Airlines
Jan 16
BOS4:16 pmBoston Logan Intl
3h 00m
ORD6:16 pmChicago O'Hare Intl
Jan 25
ORD9:13 amChicago O'Hare Intl
2h 33m
BOS12:46 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
Feb 10
BOS6:00 amBoston Logan Intl
12h 12m
1 stop
ORD5:12 pmChicago O'Hare Intl
Feb 11
ORD6:02 pmChicago O'Hare Intl
6h 11m
1 stop
BOS1:13 amBoston Logan Intl
$128
Frontier
Feb 7
BOS6:00 amBoston Logan Intl
17h 44m
1 stop
ORD10:44 pmChicago O'Hare Intl
Feb 17
ORD11:51 amChicago O'Hare Intl
12h 22m
1 stop
BOS1:13 amBoston Logan Intl
$164
Frontier
Feb 5
BDL12:11 pmHartford Bradley Intl
11h 35m
1 stop
ORD10:46 pmChicago O'Hare Intl
Feb 7
ORD9:25 amChicago O'Hare Intl
8h 41m
1 stop
BDL7:06 pmHartford Bradley Intl
$170

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 January 13, 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

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/10

6:00 am-5:12 pm

1 stop12h 12m

Chicago O'Hare Intl

Wed 2/11

6:02 pm-1:13 am

1 stop6h 11m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/3

6:00 am-1:58 pm

1 stop8h 58m

Chicago O'Hare Intl

Wed 2/4

10:48 am-11:19 pm

1 stop11h 31m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/3

5:53 pm-8:18 am

1 stop15h 25m

Chicago O'Hare Intl

Tue 2/10

10:48 am-11:19 pm

1 stop11h 31m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/18

11:31 am-11:47 pm

1 stop13h 16m

Chicago O'Hare Intl

Mon 3/2

4:42 pm-1:13 am

1 stop7h 31m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/30

12:45 pm-2:49 pm

Nonstop3h 04m

Chicago O'Hare Intl

Tue 2/3

7:30 am-10:53 am

Nonstop2h 23m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 2/2

5:23 pm-11:22 am

1 stop18h 59m

Chicago O'Hare Intl

Tue 2/10

7:20 am-11:57 pm

1 stop15h 37m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 2/20

3:50 pm-5:53 pm

Nonstop3h 03m

Chicago O'Hare Intl

Wed 2/25

10:11 am-1:35 pm

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/30

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/10

7:45 am-11:10 am

Nonstop2h 25m

$138

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 2/17

4:30 pm-10:05 pm

1 stop6h 35m

Chicago O'Hare Intl

Wed 2/18

9:35 am-3:33 pm

1 stop4h 58m

$213

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Wed 2/11

10:05 am-11:52 am

Nonstop2h 47m

Chicago O'Hare Intl

Sat 2/14

7:40 pm-10:48 pm

Nonstop2h 08m

$269

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 January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $217.

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 $317. 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 $414.

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 $367. 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 $249 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 $222 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

$135

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Massachusetts in the past 72 hours is $135. The best round-trip flight deal from Massachusetts to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $241.
The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 25m
Direct flights go from Massachusetts to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 $70Free CancellationRating
7.2
2,884 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,309 reviews
Search Spirit Airlines flights
DeltaPriceFrom $115Free CancellationRating
7.9
8,040 reviews
Search Delta flights
United AirlinesPriceFrom $122Free CancellationRating
7.4
9,156 reviews
Search United Airlines flights
American AirlinesPriceFrom $129Free CancellationRating
7.2
11,119 reviews
Search American Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,257 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
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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