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Cheap flights from Massachusetts to Chicago from $94

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 9/10. 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

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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.
Frontier Logo
12:54 pm - 6:23 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 29m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:05 am - 4:29 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
7h 24m1 stop Atlanta Hartsfield-Jackson
$162Frontier
Sat, Sep 26 - Sat, Oct 3
JetBlue Logo
5:20 pm - 7:26 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 06mnonstop
JetBlue Logo
9:38 am - 1:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 28mnonstop
$163JetBlue
Wed, Sep 2 - Thu, Sep 10
JetBlue Logo
7:00 am - 8:48 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 48mnonstop
JetBlue Logo
8:24 pm - 12:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 45mnonstop
$163JetBlue
Thu, Oct 1 - Sat, Oct 3
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
7:35 am - 11:08 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
$165Delta
Wed, Sep 16 - Tue, Sep 22
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
7:10 pm - 10:53 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 43mnonstop
$165Delta
Tue, Oct 20 - Tue, Oct 20
American Airlines Logo
7:17 pm - 9:35 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
American Airlines Logo
10:30 am - 2:08 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 38mnonstop
$165American Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
8:23 am - 10:30 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 07mnonstop
American Airlines Logo
6:00 am - 9:37 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 37mnonstop
$165American Airlines
Thu, Oct 15 - Mon, Oct 19
United Airlines Logo
7:05 am - 9:03 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
United Airlines Logo
6:24 pm - 9:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
$165United Airlines
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
8:05 am - 10:04 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
9:07 am - 12:50 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 43mnonstop
$165United Airlines
Tue, Sep 1 - Wed, Sep 2
Multiple Airlines Logo
11:28 am - 8:28 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
10h 00m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:24 pm - 11:58 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 34mnonstop
$166Multiple Airlines
Wed, Oct 21 - Sat, Oct 24

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American Airlines flights from Massachusetts to Chicago

Our best American Airlines deals on Massachusetts to Chicago flight tickets
American Airlines
Sep 10
ORH5:16 pmWorcester
7h 40m
1 stop
ORD11:56 pmChicago O'Hare Intl
Sep 17
ORD6:29 amChicago O'Hare Intl
9h 20m
1 stop
ORH4:49 pmWorcester
$193
American Airlines
Sep 18
ORH5:16 pmWorcester
18h 40m
1 stop
ORD10:56 amChicago O'Hare Intl
Sep 22
ORD8:45 amChicago O'Hare Intl
7h 04m
1 stop
ORH4:49 pmWorcester
$208
American Airlines
Aug 28
ORH5:23 pmWorcester
15h 07m
1 stop
ORD7:30 amChicago O'Hare Intl
Sep 1
ORD8:19 amChicago O'Hare Intl
7h 39m
1 stop
ORH4:58 pmWorcester
$226

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets
Frontier
Sep 26
BOS12:54 pmBoston Logan Intl
6h 29m
1 stop
ORD6:23 pmChicago O'Hare Intl
Oct 3
ORD8:05 amChicago O'Hare Intl
7h 24m
1 stop
BOS4:29 pmBoston Logan Intl
$162
Frontier
Aug 31
BOS12:45 pmBoston Logan Intl
8h 14m
1 stop
ORD7:59 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
12h 25m
1 stop
BOS9:09 amBoston Logan Intl
$168
Frontier
Oct 3
BOS12:54 pmBoston Logan Intl
6h 29m
1 stop
ORD6:23 pmChicago O'Hare Intl
Oct 4
ORD6:00 amChicago O'Hare Intl
2h 39m
BOS9:39 amBoston Logan Intl
$173

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 August 16, 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 Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 9/26

12:54 pm-6:23 pm

1 stop6h 29m

Chicago O'Hare Intl

Sat 10/3

8:05 am-4:29 pm

1 stop7h 24m

$162

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 9/2

5:20 pm-7:26 pm

Nonstop3h 06m

Chicago O'Hare Intl

Thu 9/10

9:38 am-1:06 pm

Nonstop2h 28m

$163

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 10/1

7:00 am-8:48 am

Nonstop2h 48m

Chicago O'Hare Intl

Sat 10/3

8:24 pm-12:09 am

Nonstop2h 45m

$163
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 9/16

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Tue 9/22

7:35 am-11:08 am

Nonstop2h 33m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/20

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Tue 10/20

7:10 pm-10:53 pm

Nonstop2h 43m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 9/10

7:17 pm-9:35 pm

Nonstop3h 18m

Chicago O'Hare Intl

Mon 9/14

10:30 am-2:08 pm

Nonstop2h 38m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 10/15

8:23 am-10:30 am

Nonstop3h 07m

Chicago O'Hare Intl

Mon 10/19

6:00 am-9:37 am

Nonstop2h 37m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 9/8

7:05 am-9:03 am

Nonstop2h 58m

Chicago O'Hare Intl

Tue 9/15

6:24 pm-9:59 pm

Nonstop2h 35m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 9/1

8:05 am-10:04 am

Nonstop2h 59m

Chicago O'Hare Intl

Wed 9/2

9:07 am-12:50 pm

Nonstop2h 43m

$165

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 10/21

11:28 am-8:28 pm

1 stop10h 00m

Chicago O'Hare Intl

Sat 10/24

8:24 pm-11:58 pm

Nonstop2h 34m

$166

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 January is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $197. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Massachusetts to Chicago during February average around $217.

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 $316. 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 $277. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $370.

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 $256 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 $225 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.

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

$175

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 $175. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $268.
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 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 $69Free CancellationRating
7.1
3,034 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.8
8,502 reviews
Search Delta flights
United AirlinesPriceFrom $126Free CancellationRating
7.4
10,105 reviews
Search United Airlines flights
SouthwestPriceFrom $135Free CancellationRating
8.0
4,217 reviews
Search Southwest flights
American AirlinesPriceFrom $137Free CancellationRating
7.1
11,947 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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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