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Cheap flights from Massachusetts to Chicago from $91

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 8/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:15 am - 8:25 am
MDW
-
BOS
2h 10mnonstop
$170Southwest
Fri, Jul 31 - Sun, Aug 2
United Airlines Logo
6:00 am - 7:58 am
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
7:45 pm - 11:21 pm
ORD
-
BOS
2h 36mnonstop
$170United Airlines
Sat, Jul 18 - Wed, Jul 22
JetBlue Logo
8:15 am - 10:11 am
BOS
-
ORD
2h 56mnonstop
JetBlue Logo
9:38 am - 1:06 pm
ORD
-
BOS
2h 28mnonstop
$173JetBlue
Thu, Sep 3 - Wed, Sep 9
JetBlue Logo
8:41 am - 4:17 pm
BOS
-
ORD
8h 36m
1 stop
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
$174JetBlue
Sat, Aug 22 - Mon, Aug 24
Delta Logo
7:59 pm - 9:59 pm
BOS
-
ORD
3h 00mnonstop
Delta Logo
3:19 pm - 6:59 pm
ORD
-
BOS
2h 40mnonstop
$178Delta
Sat, Jul 25 - Thu, Jul 30
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
Delta Logo
3:19 pm - 6:59 pm
ORD
-
BOS
2h 40mnonstop
$179Delta
Mon, Jul 20 - Tue, Jul 28
American Airlines Logo
5:16 pm - 6:38 am
ORH
-
ORD
14h 22m
1 stop
American Airlines Logo
6:37 am - 4:51 pm
ORD
-
ORH
9h 14m
1 stop
$192American Airlines
Thu, Jul 30 - Sun, Aug 2
American Airlines Logo
5:16 pm - 12:29 am
ORH
-
ORD
8h 13m
1 stop
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
$208American Airlines
Fri, Jul 24 - Mon, Jul 27
Multiple Airlines Logo
8:02 pm - 12:15 pm
ALB
-
ORD
17h 13m
1 stop
Multiple Airlines Logo
1:50 pm - 7:12 pm
ORD
-
ALB
28h 22m
2 stops
$301Multiple Airlines
Fri, Aug 7 - Sun, Aug 9
Multiple Airlines Logo
4:36 pm - 12:15 pm
ALB
-
ORD
20h 39m
2 stops
Multiple Airlines Logo
8:05 am - 7:12 pm
ORD
-
ALB
10h 07m
1 stop
$308Multiple Airlines
Thu, Aug 13 - Mon, Aug 17

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JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets
JetBlue
Jul 22
BOS8:10 amBoston Logan Intl
2h 56m
ORD10:06 amChicago O'Hare Intl
Jul 24
ORD8:10 pmChicago O'Hare Intl
2h 31m
BOS11:41 pmBoston Logan Intl
$170
JetBlue
Sep 2
BOS5:20 pmBoston Logan Intl
3h 06m
ORD7:26 pmChicago O'Hare Intl
Sep 9
ORD8:24 pmChicago O'Hare Intl
2h 34m
BOS11:58 pmBoston Logan Intl
$171
JetBlue
Sep 3
BOS8:15 amBoston Logan Intl
2h 56m
ORD10:11 amChicago O'Hare Intl
Sep 9
ORD9:38 amChicago O'Hare Intl
2h 28m
BOS1:06 pmBoston Logan Intl
$173

United Airlines flights from Massachusetts to Chicago

Our best United Airlines deals on Massachusetts to Chicago flight tickets
United Airlines
Jul 25
BOS8:20 pmBoston Logan Intl
3h 00m
ORD10:20 pmChicago O'Hare Intl
Jul 28
ORD6:00 amChicago O'Hare Intl
4h 16m
1 stop
BOS11:16 amBoston Logan Intl
$172
United Airlines
Jul 20
BOS7:19 amBoston Logan Intl
2h 58m
ORD9:17 amChicago O'Hare Intl
Jul 28
ORD9:41 pmChicago O'Hare Intl
2h 33m
BOS1:14 amBoston Logan Intl
$179
United Airlines
Aug 13
BOS5:45 amBoston Logan Intl
4h 53m
1 stop
ORD9:38 amChicago O'Hare Intl
Aug 17
ORD7:59 pmChicago O'Hare Intl
2h 35m
BOS11:34 pmBoston Logan Intl
$180

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 July 6, 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
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 7/31

5:25 am-7:00 am

Nonstop2h 35m

Chicago Midway

Sun 8/2

5:15 am-8:25 am

Nonstop2h 10m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/18

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Wed 7/22

7:45 pm-11:21 pm

Nonstop2h 36m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/3

8:15 am-10:11 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/9

9:38 am-1:06 pm

Nonstop2h 28m

$173

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

8:41 am-4:17 pm

1 stop8h 36m

Chicago O'Hare Intl

Mon 8/24

8:20 pm-11:51 pm

Nonstop2h 31m

$174

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/25

7:59 pm-9:59 pm

Nonstop3h 00m

Chicago O'Hare Intl

Thu 7/30

3:19 pm-6:59 pm

Nonstop2h 40m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 7/20

8:45 pm-10:39 pm

Nonstop2h 54m

Chicago O'Hare Intl

Tue 7/28

3:19 pm-6:59 pm

Nonstop2h 40m

$179

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 7/30

5:16 pm-6:38 am

1 stop14h 22m

Chicago O'Hare Intl

Sun 8/2

6:37 am-4:51 pm

1 stop9h 14m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 7/24

5:16 pm-12:29 am

1 stop8h 13m

Chicago O'Hare Intl

Mon 7/27

5:00 am-4:51 pm

1 stop10h 51m

$208

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Fri 8/7

8:02 pm-12:15 pm

1 stop17h 13m

Chicago O'Hare Intl

Sun 8/9

1:50 pm-7:12 pm

2 stops28h 22m

$301

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Thu 8/13

4:36 pm-12:15 pm

2 stops20h 39m

Chicago O'Hare Intl

Mon 8/17

8:05 am-7:12 pm

1 stop10h 07m

$308

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 $167. 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 $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 Friday when prices can be found for as low as $317. 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 $410.

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 at noon when prices are around $371.

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 $252 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 $215 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

$139

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 $139. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $237.
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
3,009 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.8
8,452 reviews
Search Delta flights
United AirlinesPriceFrom $125Free CancellationRating
7.4
9,940 reviews
Search United Airlines flights
SouthwestPriceFrom $134Free CancellationRating
7.9
4,252 reviews
Search Southwest flights
American AirlinesPriceFrom $137Free CancellationRating
7.1
11,782 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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