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Cheap flights from Massachusetts to Chicago from $82

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 5/27. 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.
JetBlue Logo
5:26 pm - 7:34 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
8:50 am - 12:20 pm
ORD
-
BOS
2h 30mnonstop
$162JetBlue
Tue, Jun 9 - Wed, Jun 10
Multiple Airlines Logo
5:45 am - 12:37 pm
BOS
-
ORD
31h 52m
1 stop
Multiple Airlines Logo
1:29 pm - 1:27 am
ORD
-
BOS
10h 58m
1 stop
$164Multiple Airlines
Tue, May 26 - Tue, Jun 9
Southwest Logo
2:25 pm - 4:05 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
5:25 am - 8:40 am
MDW
-
BOS
2h 15mnonstop
$167Southwest
Wed, Jun 3 - Sat, Jun 6
Southwest Logo
6:45 pm - 8:35 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
6:05 pm - 9:20 pm
MDW
-
BOS
2h 15mnonstop
$172Southwest
Mon, Jun 8 - Wed, Jun 10
Delta Logo
5:30 pm - 7:33 pm
BOS
-
ORD
3h 03mnonstop
Delta Logo
3:50 pm - 7:27 pm
ORD
-
BOS
2h 37mnonstop
$172Delta
Sat, May 30 - Fri, Jun 5
Delta Logo
5:30 pm - 7:33 pm
BOS
-
ORD
3h 03mnonstop
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
$174Delta
Sat, May 23 - Sun, May 24
Frontier Logo
6:00 am - 11:09 am
BOS
-
MDW
6h 09m
1 stop
Frontier Logo
12:27 pm - 1:24 am
MDW
-
BOS
11h 57m
1 stop
$180Frontier
Wed, May 27 - Tue, Jun 2
Frontier Logo
6:00 am - 11:12 am
BOS
-
MDW
6h 12m
1 stop
Frontier Logo
12:04 pm - 1:24 am
MDW
-
BOS
12h 20m
1 stop
$181Frontier
Tue, Jun 2 - Wed, Jun 3
American Airlines Logo
5:39 am - 11:00 am
ALB
-
ORD
6h 21m
1 stop
American Airlines Logo
5:10 am - 10:52 am
ORD
-
ALB
4h 42m
1 stop
$305American Airlines
Tue, Jun 9 - Wed, Jun 10
American Airlines Logo
6:15 am - 8:00 am
ALB
-
ORD
2h 45mnonstop
American Airlines Logo
5:10 am - 10:52 am
ORD
-
ALB
4h 42m
1 stop
$313American Airlines
Wed, Jun 3 - Thu, Jun 4

American Airlines flights from Massachusetts to Chicago

Our best American Airlines deals on Massachusetts to Chicago flight tickets
American Airlines
Jun 15
BOS5:00 amBoston Logan Intl
2h 58m
ORD6:58 amChicago O'Hare Intl
Jun 22
ORD6:04 amChicago O'Hare Intl
2h 26m
BOS9:30 amBoston Logan Intl
$178
American Airlines
May 30
BOS5:05 amBoston Logan Intl
2h 57m
ORD7:02 amChicago O'Hare Intl
May 31
ORD6:00 amChicago O'Hare Intl
2h 27m
BOS9:27 amBoston Logan Intl
$188
American Airlines
May 18
BOS6:30 amBoston Logan Intl
3h 14m
ORD8:44 amChicago O'Hare Intl
May 24
ORD6:00 amChicago O'Hare Intl
2h 27m
BOS9:27 amBoston Logan Intl
$191

United Airlines flights from Massachusetts to Chicago

Our best United Airlines deals on Massachusetts to Chicago flight tickets
United Airlines
Jun 18
BOS6:40 pmBoston Logan Intl
3h 00m
ORD8:40 pmChicago O'Hare Intl
Jun 22
ORD9:41 pmChicago O'Hare Intl
2h 33m
BOS1:14 amBoston Logan Intl
$177
United Airlines
Jun 10
BOS6:00 amBoston Logan Intl
2h 58m
ORD7:58 amChicago O'Hare Intl
Jun 19
ORD6:20 pmChicago O'Hare Intl
2h 36m
BOS9:56 pmBoston Logan Intl
$186
United Airlines
Jun 11
BOS8:15 amBoston Logan Intl
2h 57m
ORD10:12 amChicago O'Hare Intl
Jun 14
ORD6:05 amChicago O'Hare Intl
2h 24m
BOS9:29 amBoston Logan Intl
$191

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 May 5, 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

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/9

5:26 pm-7:34 pm

Nonstop3h 08m

Chicago O'Hare Intl

Wed 6/10

8:50 am-12:20 pm

Nonstop2h 30m

$162

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/26

5:45 am-12:37 pm

1 stop31h 52m

Chicago O'Hare Intl

Tue 6/9

1:29 pm-1:27 am

1 stop10h 58m

$164
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 6/3

2:25 pm-4:05 pm

Nonstop2h 40m

Chicago Midway

Sat 6/6

5:25 am-8:40 am

Nonstop2h 15m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 6/8

6:45 pm-8:35 pm

Nonstop2h 50m

Chicago Midway

Wed 6/10

6:05 pm-9:20 pm

Nonstop2h 15m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

5:30 pm-7:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Fri 6/5

3:50 pm-7:27 pm

Nonstop2h 37m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/23

5:30 pm-7:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sun 5/24

7:00 am-10:35 am

Nonstop2h 35m

$174

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/27

6:00 am-11:09 am

1 stop6h 09m

Chicago Midway

Tue 6/2

12:27 pm-1:24 am

1 stop11h 57m

$180

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 6/2

6:00 am-11:12 am

1 stop6h 12m

Chicago Midway

Wed 6/3

12:04 pm-1:24 am

1 stop12h 20m

$181

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Tue 6/9

5:39 am-11:00 am

1 stop6h 21m

Chicago O'Hare Intl

Wed 6/10

5:10 am-10:52 am

1 stop4h 42m

$305

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Wed 6/3

6:15 am-8:00 am

Nonstop2h 45m

Chicago O'Hare Intl

Thu 6/4

5:10 am-10:52 am

1 stop4h 42m

$313

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 $166. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Massachusetts to Chicago during February average around $203.

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 Friday when prices can be found for as low as $315. 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 $363.

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 from Massachusetts 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 $220 on momondo.

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 05m

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 $227.
The fastest flight from Massachusetts to Chicago takes 2h 05m
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

Frequently asked questions about flying from Massachusetts to Chicago

  • 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 $68Free CancellationRating
7.1
2,978 reviews
Search JetBlue flights
DeltaPriceFrom $87Free CancellationRating
7.9
8,459 reviews
Search Delta flights
Spirit AirlinesPriceFrom $95Free CancellationRating
6.3
8,634 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $119Free CancellationRating
7.4
9,683 reviews
Search United Airlines flights
SouthwestPriceFrom $125Free CancellationRating
7.9
4,305 reviews
Search Southwest flights
American AirlinesPriceFrom $133Free CancellationRating
7.1
11,672 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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