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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 3/20. 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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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
9:00 am - 3:30 pm
BOS
-
ORD
7h 30m
1 stop
Southwest Logo
2:40 pm - 10:30 pm
ORD
-
BOS
6h 50m
1 stop
$128Southwest
Sat, May 9 - Tue, May 12
Multiple Airlines Logo
7:35 pm - 9:39 pm
BOS
-
ORD
3h 04mnonstop
Multiple Airlines Logo
4:28 pm - 1:31 am
ORD
-
BOS
8h 03m
1 stop
$129Multiple Airlines
Tue, Apr 14 - Thu, Apr 16
United Airlines Logo
6:00 am - 7:59 am
BOS
-
ORD
2h 59mnonstop
United Airlines Logo
9:30 pm - 12:59 am
ORD
-
BOS
2h 29mnonstop
$131United Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:03 am - 10:12 am
BOS
-
ORD
3h 09mnonstop
American Airlines Logo
3:16 pm - 6:50 pm
ORD
-
BOS
2h 34mnonstop
$132American Airlines
Sun, Apr 12 - Wed, Apr 15
United Airlines Logo
8:10 pm - 10:05 pm
BOS
-
ORD
2h 55mnonstop
United Airlines Logo
6:00 am - 9:25 am
ORD
-
BOS
2h 25mnonstop
$133United Airlines
Fri, May 1 - Mon, May 4
JetBlue Logo
6:05 am - 8:08 am
BOS
-
ORD
3h 03mnonstop
JetBlue Logo
6:00 am - 9:13 am
ORD
-
BOS
2h 13mnonstop
$135JetBlue
Sat, Apr 11 - Thu, Apr 16
JetBlue Logo
8:00 am - 10:10 am
BOS
-
ORD
3h 10mnonstop
JetBlue Logo
6:20 pm - 9:53 pm
ORD
-
BOS
2h 33mnonstop
$136JetBlue
Tue, Mar 24 - Thu, Mar 26
Delta Logo
7:15 am - 9:25 am
BOS
-
ORD
3h 10mnonstop
Delta Logo
6:15 am - 9:40 am
ORD
-
BOS
2h 25mnonstop
$137Delta
Thu, Apr 2 - Sun, Apr 5
American Airlines Logo
2:39 pm - 7:39 am
ORH
-
ORD
18h 00m
1 stop
American Airlines Logo
7:15 pm - 2:14 pm
ORD
-
ORH
17h 59m
1 stop
$160American Airlines
Tue, Apr 28 - Sat, May 2
Delta Logo
4:59 pm - 10:43 pm
MVY
-
ORD
6h 44m
1 stop
Delta Logo
10:35 am - 4:17 pm
ORD
-
MVY
4h 42m
1 stop
$196Delta
Thu, Aug 20 - Mon, Aug 24

Southwest flights from Massachusetts to Chicago O'Hare Intl Airport

Our best Southwest deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
Southwest
May 9
BOS9:00 amBoston Logan Intl
7h 30m
1 stop
ORD3:30 pmChicago O'Hare Intl
May 11
ORD2:40 pmChicago O'Hare Intl
7h 35m
1 stop
BOS11:15 pmBoston Logan Intl
$128
Southwest
May 9
BOS5:25 amBoston Logan Intl
11h 05m
2 stops
ORD3:30 pmChicago O'Hare Intl
May 11
ORD2:40 pmChicago O'Hare Intl
7h 35m
1 stop
BOS11:15 pmBoston Logan Intl
$134
Southwest
May 1
BOS7:25 pmBoston Logan Intl
14h 45m
2 stops
ORD9:10 amChicago O'Hare Intl
May 5
ORD2:40 pmChicago O'Hare Intl
6h 50m
1 stop
BOS10:30 pmBoston Logan Intl
$148

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
Mar 30
BOS6:00 amBoston Logan Intl
2h 59m
ORD7:59 amChicago O'Hare Intl
Apr 6
ORD9:30 pmChicago O'Hare Intl
2h 29m
BOS12:59 amBoston Logan Intl
$131
United Airlines
May 1
BOS8:10 pmBoston Logan Intl
2h 55m
ORD10:05 pmChicago O'Hare Intl
May 4
ORD6:00 amChicago O'Hare Intl
2h 25m
BOS9:25 amBoston Logan Intl
$133
United Airlines
Apr 4
BOS6:00 amBoston Logan Intl
2h 59m
ORD7:59 amChicago O'Hare Intl
Apr 5
ORD7:30 amChicago O'Hare Intl
2h 31m
BOS11:01 amBoston Logan Intl
$140

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 March 2, 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

Sat 5/9

9:00 am-3:30 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 5/12

2:40 pm-10:30 pm

1 stop6h 50m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/14

7:35 pm-9:39 pm

Nonstop3h 04m

Chicago O'Hare Intl

Thu 4/16

4:28 pm-1:31 am

1 stop8h 03m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/30

6:00 am-7:59 am

Nonstop2h 59m

Chicago O'Hare Intl

Mon 4/6

9:30 pm-12:59 am

Nonstop2h 29m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 4/12

8:03 am-10:12 am

Nonstop3h 09m

Chicago O'Hare Intl

Wed 4/15

3:16 pm-6:50 pm

Nonstop2h 34m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/1

8:10 pm-10:05 pm

Nonstop2h 55m

Chicago O'Hare Intl

Mon 5/4

6:00 am-9:25 am

Nonstop2h 25m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/11

6:05 am-8:08 am

Nonstop3h 03m

Chicago O'Hare Intl

Thu 4/16

6:00 am-9:13 am

Nonstop2h 13m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/24

8:00 am-10:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Thu 3/26

6:20 pm-9:53 pm

Nonstop2h 33m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/2

7:15 am-9:25 am

Nonstop3h 10m

Chicago O'Hare Intl

Sun 4/5

6:15 am-9:40 am

Nonstop2h 25m

$137

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/28

2:39 pm-7:39 am

1 stop18h 00m

Chicago O'Hare Intl

Sat 5/2

7:15 pm-2:14 pm

1 stop17h 59m

$160

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 8/20

4:59 pm-10:43 pm

1 stop6h 44m

Chicago O'Hare Intl

Mon 8/24

10:35 am-4:17 pm

1 stop4h 42m

$196

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 $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 $404.

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 $274 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $383. 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 $247 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 $219 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 32m

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 $229.
The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 32m
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 $66Free CancellationRating
7.2
2,894 reviews
Search JetBlue flights
DeltaPriceFrom $83Free CancellationRating
7.9
8,237 reviews
Search Delta flights
Spirit AirlinesPriceFrom $85Free CancellationRating
6.3
8,486 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,375 reviews
Search United Airlines flights
American AirlinesPriceFrom $127Free CancellationRating
7.1
11,369 reviews
Search American Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,307 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
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
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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