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Cheap flights from Massachusetts to Chicago from $59

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 12/31. 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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Cheap round-trip flights

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Southwest Logo
1:35 pm - 3:20 pmBOS-MDW
2h 45mnonstop
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$117Southwest
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Tue, Dec 9 - Tue, Dec 16
JetBlue Logo
8:30 am - 10:35 amBOS-ORD
3h 05mnonstop
JetBlue Logo
7:41 pm - 11:10 pmORD-BOS
2h 29mnonstop
$117JetBlue
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Tue, Dec 16 - Mon, Dec 22
United Airlines Logo
4:20 pm - 6:20 pmBOS-ORD
3h 00mnonstop
United Airlines Logo
1:55 pm - 5:15 pmORD-BOS
2h 20mnonstop
$122United Airlines
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Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
1:45 pm - 3:55 pmBOS-ORD
3h 10mnonstop
American Airlines Logo
6:10 am - 9:35 amORD-BOS
2h 25mnonstop
$123American Airlines
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Wed, Dec 10 - Sat, Dec 13
United Airlines Logo
6:23 pm - 8:23 pmBOS-ORD
3h 00mnonstop
United Airlines Logo
11:20 am - 2:44 pmORD-BOS
2h 24mnonstop
$124United Airlines
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Tue, Dec 16 - Thu, Dec 18
American Airlines Logo
6:36 am - 8:47 amBOS-ORD
3h 11mnonstop
American Airlines Logo
8:20 pm - 11:51 pmORD-BOS
2h 31mnonstop
$125American Airlines
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Thu, Jan 1 - Mon, Jan 5
Frontier Logo
11:28 am - 5:27 pmBOS-ORD
6h 59m1 stop
Frontier Logo
6:00 am - 12:02 pmORD-BOS
5h 02m1 stop
$128Frontier
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Thu, Dec 4 - Sun, Dec 7
Frontier Logo
6:00 am - 10:13 pmBOS-MDW
17h 13m1 stop
Frontier Logo
8:28 am - 1:13 amMDW-BOS
15h 45m1 stop
$130Frontier
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Sat, Jan 17 - Mon, Jan 19
Multiple Airlines Logo
12:57 pm - 9:48 amBOS-RFD
21h 51m1 stop
Multiple Airlines Logo
10:38 am - 9:52 amRFD-BOS
22h 14m1 stop
$207Multiple Airlines
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Sun, Dec 14 - Wed, Dec 17
Multiple Airlines Logo
12:17 pm - 12:48 pmBOS-RFD
25h 31m1 stop
Multiple Airlines Logo
10:38 am - 10:01 amRFD-BOS
22h 23m1 stop
$217Multiple Airlines
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Fri, Dec 5 - Mon, Dec 8

United Airlines flights from Massachusetts to Chicago

Our best United Airlines deals on Massachusetts to Chicago flight tickets
United Airlines
Dec 9
BOS4:20 pmBoston Logan Intl
3h 00m
ORD6:20 pmChicago O'Hare Intl
Dec 16
ORD1:55 pmChicago O'Hare Intl
2h 20m
BOS5:15 pmBoston Logan Intl
$122
Find similar
United Airlines
Dec 16
BOS6:23 pmBoston Logan Intl
3h 00m
ORD8:23 pmChicago O'Hare Intl
Dec 18
ORD11:20 amChicago O'Hare Intl
2h 24m
BOS2:44 pmBoston Logan Intl
$124
Find similar
United Airlines
Dec 5
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
Dec 7
ORD7:30 amChicago O'Hare Intl
2h 19m
BOS10:49 amBoston Logan Intl
$127
Find similar

American Airlines flights from Massachusetts to Chicago

Our best American Airlines deals on Massachusetts to Chicago flight tickets
American Airlines
Dec 10
BOS1:45 pmBoston Logan Intl
3h 10m
ORD3:55 pmChicago O'Hare Intl
Dec 13
ORD6:10 amChicago O'Hare Intl
2h 25m
BOS9:35 amBoston Logan Intl
$123
Find similar
American Airlines
Jan 1
BOS6:36 amBoston Logan Intl
3h 11m
ORD8:47 amChicago O'Hare Intl
Jan 5
ORD8:20 pmChicago O'Hare Intl
2h 31m
BOS11:51 pmBoston Logan Intl
$125
Find similar
American Airlines
Dec 14
BOS6:00 amBoston Logan Intl
3h 17m
ORD8:17 amChicago O'Hare Intl
Dec 18
ORD8:20 pmChicago O'Hare Intl
2h 31m
BOS11:51 pmBoston Logan Intl
$129
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Chicago 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 November 19, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 12/9

1:35 pm-3:20 pm

Nonstop2h 45m

Chicago Midway

Tue 12/16

6:15 pm-9:35 pm

Nonstop2h 20m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/16

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Mon 12/22

7:41 pm-11:10 pm

Nonstop2h 29m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/9

4:20 pm-6:20 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 12/16

1:55 pm-5:15 pm

Nonstop2h 20m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/10

1:45 pm-3:55 pm

Nonstop3h 10m

Chicago O'Hare Intl

Sat 12/13

6:10 am-9:35 am

Nonstop2h 25m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/16

6:23 pm-8:23 pm

Nonstop3h 00m

Chicago O'Hare Intl

Thu 12/18

11:20 am-2:44 pm

Nonstop2h 24m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/1

6:36 am-8:47 am

Nonstop3h 11m

Chicago O'Hare Intl

Mon 1/5

8:20 pm-11:51 pm

Nonstop2h 31m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/4

11:28 am-5:27 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 12/7

6:00 am-12:02 pm

1 stop5h 02m

$128

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

6:00 am-10:13 pm

1 stop17h 13m

Chicago Midway

Mon 1/19

8:28 am-1:13 am

1 stop15h 45m

$130

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Sun 12/14

12:57 pm-9:48 am

1 stop21h 51m

Chicago Greater Rockford

Wed 12/17

10:38 am-9:52 am

1 stop22h 14m

$207

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Fri 12/5

12:17 pm-12:48 pm

1 stop25h 31m

Chicago Greater Rockford

Mon 12/8

10:38 am-10:01 am

1 stop22h 23m

$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

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?

The month of September is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Massachusetts to Chicago during January average around $192.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday 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. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Chicago for around $429.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Massachusetts to Chicago during this time can be as low as $272. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

What is the cheapest Massachusetts to Chicago flight route?

Fly from Boston Logan Intl to Chicago Midway for the best Massachusetts - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $250 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Massachusetts for as low as $222 on momondo.

What cabin class options are available on Massachusetts to Chicago flights?

There are 4 cabin classes available to choose from on Massachusetts to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Massachusetts to Chicago.

Cheap Massachusetts to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago

Best Price Found

$123

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Massachusetts in the past 72 hours is $123. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $191.
The fastest flight from Massachusetts to Chicago takes 2h 10m
Direct flights go from Massachusetts to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • When did momondo last update prices for flights from Massachusetts to Chicago?

    Prices for flights from Massachusetts to Chicago are updated daily.

  • How many operators does momondo search for flights from Massachusetts to Chicago?

  • How old do you have to be to fly from Massachusetts to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Massachusetts to Chicago?

Best airlines flying from Massachusetts to Chicago

Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $71Free CancellationRating
6.3
8,151 reviews
Search Spirit Airlines flights
JetBluePriceFrom $79Free CancellationRating
7.2
2,902 reviews
Search JetBlue flights
FrontierPriceFrom $89Free CancellationRating
5.8
3,105 reviews
Search Frontier flights
DeltaPriceFrom $116Free CancellationRating
7.9
8,002 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
United AirlinesPriceFrom $126Free CancellationRating
7.4
9,019 reviews
Search United Airlines flights
American AirlinesPriceFrom $135Free CancellationRating
7.2
11,044 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

momondo does allow users to show only those flights to Chicago from Massachusetts which offer a flexible booking policy as well as other useful filters and features.

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?

Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport