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Cheap flights from Massachusetts to Chicago from $64

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 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Spirit Airlines Logo
6:16 am - 6:38 pmBOS-ORD
13h 22m1 stop
Spirit Airlines Logo
6:00 am - 1:20 pmORD-BOS
6h 20m1 stop
$126Spirit Airlines
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Wed, Oct 15 - Tue, Oct 21
JetBlue Logo
8:30 am - 10:35 amBOS-ORD
3h 05mnonstop
JetBlue Logo
8:45 pm - 12:13 amORD-BOS
2h 28mnonstop
$127JetBlue
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Wed, Nov 19 - Sat, Nov 22
United Airlines Logo
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
United Airlines Logo
9:20 pm - 12:50 amORD-BOS
2h 30mnonstop
$131United Airlines
Find Deal
Thu, Oct 16 - Wed, Oct 22
United Airlines Logo
3:17 pm - 5:07 pmBOS-ORD
2h 50mnonstop
United Airlines Logo
7:30 am - 11:02 amORD-BOS
2h 32mnonstop
$134United Airlines
Find Deal
Tue, Oct 7 - Wed, Oct 8
Delta Logo
7:30 pm - 9:19 pmBOS-ORD
2h 49mnonstop
Delta Logo
7:05 am - 10:29 amORD-BOS
2h 24mnonstop
$137Delta
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Tue, Oct 7 - Sun, Oct 12
American Airlines Logo
5:24 am - 7:25 amBOS-ORD
3h 01mnonstop
American Airlines Logo
11:45 am - 3:03 pmORD-BOS
2h 18mnonstop
$145American Airlines
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Fri, Oct 31 - Wed, Nov 5
American Airlines Logo
5:24 am - 7:25 amBOS-ORD
3h 01mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$146American Airlines
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Thu, Oct 23 - Sun, Oct 26
Southwest Logo
7:15 am - 12:45 pmBOS-ORD
6h 30m1 stop
Southwest Logo
3:10 pm - 10:15 pmORD-BOS
6h 05m1 stop
$147Southwest
Find Deal
Fri, Oct 3 - Tue, Oct 7
Delta Logo
7:20 am - 9:22 amBOS-ORD
3h 02mnonstop
Delta Logo
10:25 am - 1:55 pmORD-BOS
2h 30mnonstop
$148Delta
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
5:00 am - 12:45 pmBOS-ORD
8h 45m1 stop
Southwest Logo
3:10 pm - 10:15 pmORD-BOS
6h 05m1 stop
$152Southwest
Find Deal
Sun, Oct 5 - Tue, Oct 7

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

Our best American Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
American Airlines
Oct 31
BOS5:24 amBoston Logan Intl
3h 01m
ORD7:25 amChicago O'Hare Intl
Nov 5
ORD11:45 amChicago O'Hare Intl
2h 18m
BOS3:03 pmBoston Logan Intl
$145
Find similar
American Airlines
Oct 7
BOS5:24 amBoston Logan Intl
3h 01m
ORD7:25 amChicago O'Hare Intl
Oct 15
ORD6:05 amChicago O'Hare Intl
2h 27m
BOS9:32 amBoston Logan Intl
$146
Find similar
American Airlines
Jan 16
ORH3:25 pmWorcester
20h 26m
1 stop
ORD10:51 amChicago O'Hare Intl
Jan 18
ORD8:25 pmChicago O'Hare Intl
17h 28m
1 stop
ORH2:53 pmWorcester
$154
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Spirit Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Oct 15
BOS6:16 amBoston Logan Intl
13h 22m
1 stop
ORD6:38 pmChicago O'Hare Intl
Oct 21
ORD6:00 amChicago O'Hare Intl
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
$126
Find similar
Spirit Airlines
Oct 15
BOS3:00 pmBoston Logan Intl
9h 45m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 21
ORD6:00 amChicago O'Hare Intl
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
$128
Find similar
Spirit Airlines
Oct 21
BOS3:00 pmBoston Logan Intl
9h 45m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 28
ORD6:00 amChicago O'Hare Intl
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
$139
Find similar

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 September 23, 2025.
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

Wed 10/15

6:16 am-6:38 pm

1 stop13h 22m

Chicago O'Hare Intl

Tue 10/21

6:00 am-1:20 pm

1 stop6h 20m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 11/19

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Sat 11/22

8:45 pm-12:13 am

Nonstop2h 28m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/16

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 10/22

9:20 pm-12:50 am

Nonstop2h 30m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/7

3:17 pm-5:07 pm

Nonstop2h 50m

Chicago O'Hare Intl

Wed 10/8

7:30 am-11:02 am

Nonstop2h 32m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/7

7:30 pm-9:19 pm

Nonstop2h 49m

Chicago O'Hare Intl

Sun 10/12

7:05 am-10:29 am

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/31

5:24 am-7:25 am

Nonstop3h 01m

Chicago O'Hare Intl

Wed 11/5

11:45 am-3:03 pm

Nonstop2h 18m

$145

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

5:24 am-7:25 am

Nonstop3h 01m

Chicago O'Hare Intl

Sun 10/26

6:05 am-9:32 am

Nonstop2h 27m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/3

7:15 am-12:45 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 10/7

3:10 pm-10:15 pm

1 stop6h 05m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/31

7:20 am-9:22 am

Nonstop3h 02m

Chicago O'Hare Intl

Tue 11/4

10:25 am-1:55 pm

Nonstop2h 30m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 10/5

5:00 am-12:45 pm

1 stop8h 45m

Chicago O'Hare Intl

Tue 10/7

3:10 pm-10:15 pm

1 stop6h 05m

$152

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 $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 Friday when prices can be found for as low as $321. 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 $426.

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 $267 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $352. 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 $216 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

$106

Fastest flight time

2h 28m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Massachusetts in the past 72 hours is $106. The best round-trip flight deal from Massachusetts to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $204.
The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 28m
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
Spirit AirlinesPriceFrom $67Free CancellationRating
6.3
8,041 reviews
Search Spirit Airlines flights
JetBluePriceFrom $84Free CancellationRating
7.2
2,912 reviews
Search JetBlue flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,165 reviews
Search Frontier flights
DeltaPriceFrom $111Free CancellationRating
7.9
7,974 reviews
Search Delta flights
United AirlinesPriceFrom $137Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,244 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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