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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 2/20. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 6:38 pm
BOS
-
MDW
13h 38m
1 stop
Frontier Logo
6:00 am - 1:13 am
MDW
-
BOS
18h 13m
1 stop
$132Frontier
Fri, Feb 27 - Mon, Mar 2
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
9:40 am - 3:34 pm
ORD
-
BOS
4h 54m
1 stop
$132JetBlue
Sat, Feb 7 - Mon, Feb 9
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$133JetBlue
Sat, Feb 7 - Mon, Feb 9
United Airlines Logo
12:45 pm - 2:49 pm
BOS
-
ORD
3h 04mnonstop
United Airlines Logo
7:30 am - 10:52 am
ORD
-
BOS
2h 22mnonstop
$135United Airlines
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
6:10 am - 8:20 am
BOS
-
ORD
3h 10mnonstop
American Airlines Logo
5:25 pm - 8:45 pm
ORD
-
BOS
2h 20mnonstop
$136American Airlines
Sat, Feb 7 - Mon, Feb 9
Southwest Logo
5:45 pm - 7:35 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
$137Southwest
Fri, Feb 6 - Sat, Feb 7
Delta Logo
7:30 am - 9:41 am
BOS
-
ORD
3h 11mnonstop
Delta Logo
7:05 am - 10:40 am
ORD
-
BOS
2h 35mnonstop
$137Delta
Sat, Jan 31 - Wed, Feb 11
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
$138Southwest
Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
2:18 pm - 6:34 pm
ORH
-
ORD
5h 16m
1 stop
American Airlines Logo
8:09 am - 1:53 pm
ORD
-
ORH
4h 44m
1 stop
$155American Airlines
Sun, Feb 1 - Thu, Feb 5
United Airlines Logo
6:00 am - 7:46 am
ALB
-
ORD
2h 46mnonstop
United Airlines Logo
8:52 am - 2:05 pm
ORD
-
ALB
4h 13m
1 stop
$277United Airlines
Sat, Feb 7 - Tue, Feb 10

Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets
Delta
Jan 31
BOS7:30 amBoston Logan Intl
3h 11m
ORD9:41 amChicago O'Hare Intl
Feb 6
ORD7:05 amChicago O'Hare Intl
2h 35m
BOS10:40 amBoston Logan Intl
$137
Delta
Jan 28
BOS11:30 amBoston Logan Intl
3h 09m
ORD1:39 pmChicago O'Hare Intl
Jan 31
ORD2:00 pmChicago O'Hare Intl
2h 29m
BOS5:29 pmBoston Logan Intl
$142
Delta
Feb 6
BOS4:10 pmBoston Logan Intl
3h 09m
ORD6:19 pmChicago O'Hare Intl
Feb 16
ORD7:05 amChicago O'Hare Intl
2h 32m
BOS10:37 amBoston Logan Intl
$147

American Airlines flights from Massachusetts to Chicago

Our best American Airlines deals on Massachusetts to Chicago flight tickets
American Airlines
Feb 7
BOS6:10 amBoston Logan Intl
3h 10m
ORD8:20 amChicago O'Hare Intl
Feb 9
ORD5:25 pmChicago O'Hare Intl
2h 20m
BOS8:45 pmBoston Logan Intl
$136
American Airlines
Feb 7
BOS7:00 amBoston Logan Intl
3h 05m
ORD9:05 amChicago O'Hare Intl
Feb 16
ORD7:40 pmChicago O'Hare Intl
2h 21m
BOS11:01 pmBoston Logan Intl
$151
American Airlines
Feb 1
ORH2:18 pmWorcester
5h 16m
1 stop
ORD6:34 pmChicago O'Hare Intl
Feb 5
ORD8:09 amChicago O'Hare Intl
4h 44m
1 stop
ORH1:53 pmWorcester
$155

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 18, 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

Fri 2/27

6:00 am-6:38 pm

1 stop13h 38m

Chicago Midway

Mon 3/2

6:00 am-1:13 am

1 stop18h 13m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/7

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/9

9:40 am-3:34 pm

1 stop4h 54m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/7

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/9

7:45 am-11:10 am

Nonstop2h 25m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/29

12:45 pm-2:49 pm

Nonstop3h 04m

Chicago O'Hare Intl

Mon 2/2

7:30 am-10:52 am

Nonstop2h 22m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/7

6:10 am-8:20 am

Nonstop3h 10m

Chicago O'Hare Intl

Mon 2/9

5:25 pm-8:45 pm

Nonstop2h 20m

$136

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 2/6

5:45 pm-7:35 pm

Nonstop2h 50m

Chicago Midway

Sat 2/7

10:15 am-1:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/31

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Wed 2/11

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/23

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Fri 2/27

6:05 am-9:25 am

Nonstop2h 20m

$138

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 2/1

2:18 pm-6:34 pm

1 stop5h 16m

Chicago O'Hare Intl

Thu 2/5

8:09 am-1:53 pm

1 stop4h 44m

$155

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Sat 2/7

6:00 am-7:46 am

Nonstop2h 46m

Chicago O'Hare Intl

Tue 2/10

8:52 am-2:05 pm

1 stop4h 13m

$277

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 $205.

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 $312. 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 $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $356.

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 $248 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 $223 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

$129

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 $129. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $228.
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 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 $45Free CancellationRating
6.3
8,340 reviews
Search Spirit Airlines flights
JetBluePriceFrom $67Free CancellationRating
7.2
2,891 reviews
Search JetBlue flights
DeltaPriceFrom $82Free CancellationRating
7.9
8,075 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,261 reviews
Search Southwest flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,175 reviews
Search United Airlines flights
American AirlinesPriceFrom $128Free CancellationRating
7.2
11,155 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