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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 2/25. 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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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:00 am - 12:46 pm
BOS
-
MDW
4h 46m1 stop
Delta Logo
9:34 am - 3:53 pm
MDW
-
BOS
5h 19m1 stop
$125Delta
Tue, Feb 17 - Tue, Feb 24
Delta Logo
5:00 pm - 10:05 pm
BOS
-
ORD
6h 05m1 stop
Delta Logo
10:35 am - 3:53 pm
ORD
-
BOS
4h 18m1 stop
$125Delta
Tue, Feb 17 - Wed, Feb 25
Southwest Logo
6:25 pm - 8:25 pm
BOS
-
MDW
3h 00mnonstop
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
BOS
2h 15mnonstop
$126Southwest
Thu, Mar 5 - Sat, Mar 7
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
8:55 am - 12:21 pm
ORD
-
BOS
2h 26mnonstop
$128JetBlue
Thu, Jan 29 - Mon, Feb 2
Southwest Logo
5:50 am - 11:35 am
BOS
-
MDW
6h 45m1 stop
Southwest Logo
2:20 pm - 10:05 pm
MDW
-
BOS
6h 45m2 stops
$130Southwest
Thu, Jan 29 - Mon, Feb 2
JetBlue Logo
1:40 pm - 7:36 pm
BOS
-
ORD
6h 56m1 stop
JetBlue Logo
8:55 am - 12:21 pm
ORD
-
BOS
2h 26mnonstop
$130JetBlue
Thu, Jan 29 - Mon, Feb 2
Frontier Logo
12:11 pm - 10:19 pm
BDL
-
MDW
11h 08m1 stop
Frontier Logo
6:25 am - 1:32 pm
MDW
-
BDL
6h 07m1 stop
$160Frontier
Thu, Feb 5 - Thu, Feb 12
American Airlines Logo
2:18 pm - 11:27 pm
ORH
-
ORD
10h 09m2 stops
American Airlines Logo
8:56 pm - 1:58 pm
ORD
-
ORH
16h 02m1 stop
$164American Airlines
Wed, Jan 21 - Fri, Jan 23
Frontier Logo
8:31 pm - 10:35 am
BDL
-
ORD
15h 04m1 stop
Frontier Logo
11:51 am - 11:24 am
ORD
-
BDL
22h 33m1 stop
$166Frontier
Thu, Feb 5 - Mon, Feb 9
American Airlines Logo
2:18 pm - 8:31 am
ORH
-
ORD
19h 13m2 stops
American Airlines Logo
8:18 pm - 1:58 pm
ORD
-
ORH
16h 40m2 stops
$170American Airlines
Wed, Jan 21 - Fri, Jan 23

Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets
Delta
Feb 17
BOS5:00 pmBoston Logan Intl
6h 05m
1 stop
ORD10:05 pmChicago O'Hare Intl
Feb 25
ORD10:35 amChicago O'Hare Intl
4h 18m
1 stop
BOS3:53 pmBoston Logan Intl
$125
Delta
Jan 30
BOS7:30 amBoston Logan Intl
3h 11m
ORD9:41 amChicago O'Hare Intl
Jan 31
ORD2:00 pmChicago O'Hare Intl
2h 29m
BOS5:29 pmBoston Logan Intl
$126
Delta
Feb 9
BOS4:58 pmBoston Logan Intl
5h 07m
1 stop
ORD9:05 pmChicago O'Hare Intl
Feb 17
ORD9:35 amChicago O'Hare Intl
5h 45m
1 stop
BOS4:20 pmBoston Logan Intl
$127

Spirit Airlines flights from Massachusetts to Chicago

Our best Spirit Airlines deals on Massachusetts to Chicago flight tickets
Spirit Airlines
Jan 26
BOS5:27 pmBoston Logan Intl
18h 55m
1 stop
ORD11:22 amChicago O'Hare Intl
Jan 28
ORD7:20 amChicago O'Hare Intl
15h 37m
1 stop
BOS11:57 pmBoston Logan Intl
$139
Spirit Airlines
Jan 24
BOS7:00 amBoston Logan Intl
11h 52m
1 stop
ORD5:52 pmChicago O'Hare Intl
Jan 26
ORD8:43 pmChicago O'Hare Intl
26h 14m
1 stop
BOS11:57 pmBoston Logan Intl
$145
Spirit Airlines
Jan 27
BOS5:34 amBoston Logan Intl
16h 29m
1 stop
ORD9:03 pmChicago O'Hare Intl
Jan 28
ORD6:05 amChicago O'Hare Intl
16h 52m
2 stops
BOS11:57 pmBoston Logan Intl
$159

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 January 8, 2026.
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 2/17

9:00 am-12:46 pm

1 stop4h 46m

Chicago Midway

Tue 2/24

9:34 am-3:53 pm

1 stop5h 19m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/17

5:00 pm-10:05 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 2/25

10:35 am-3:53 pm

1 stop4h 18m

$125

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 3/5

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago Midway

Sat 3/7

6:45 pm-10:00 pm

Nonstop2h 15m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/29

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/2

8:55 am-12:21 pm

Nonstop2h 26m

$128

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/29

5:50 am-11:35 am

1 stop6h 45m

Chicago Midway

Mon 2/2

2:20 pm-10:05 pm

2 stops6h 45m

$130

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/29

1:40 pm-7:36 pm

1 stop6h 56m

Chicago O'Hare Intl

Mon 2/2

8:55 am-12:21 pm

Nonstop2h 26m

$130

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 2/5

12:11 pm-10:19 pm

1 stop11h 08m

Chicago Midway

Thu 2/12

6:25 am-1:32 pm

1 stop6h 07m

$160

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 1/21

2:18 pm-11:27 pm

2 stops10h 09m

Chicago O'Hare Intl

Fri 1/23

8:56 pm-1:58 pm

1 stop16h 02m

$164

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 2/5

8:31 pm-10:35 am

1 stop15h 04m

Chicago O'Hare Intl

Mon 2/9

11:51 am-11:24 am

1 stop22h 33m

$166

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 1/21

2:18 pm-8:31 am

2 stops19h 13m

Chicago O'Hare Intl

Fri 1/23

8:18 pm-1:58 pm

2 stops16h 40m

$170

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 $202.

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 $313. 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 $412.

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 $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $351.

What is the cheapest Massachusetts to Chicago flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl 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 $249 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

$150

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Massachusetts in the past 72 hours is $150. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $252.
The fastest flight from Massachusetts to Chicago takes 2h 10m
Direct flights go from Massachusetts to Chicago every day.
There are 3 airports in Chicago. From Massachusetts there are direct flights to 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
JetBluePriceFrom $73Free CancellationRating
7.2
2,894 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,288 reviews
Search Spirit Airlines flights
DeltaPriceFrom $114Free CancellationRating
7.9
8,025 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
United AirlinesPriceFrom $124Free CancellationRating
7.4
9,139 reviews
Search United Airlines flights
American AirlinesPriceFrom $128Free CancellationRating
7.2
11,094 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
Munster
Crown Point
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