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Cheap flights from Massachusetts to Chicago from $64

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 1/17. 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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:00 am - 8:04 am
BOS
-
ORD
3h 04mnonstop
United Airlines Logo
6:05 pm - 9:38 pm
ORD
-
BOS
2h 33mnonstop
$127United Airlines
Sat, Jan 17 - Sat, Jan 17
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
$128Frontier
Wed, Jan 21 - Wed, Jan 28
Frontier Logo
6:00 am - 6:27 pm
BOS
-
ORD
13h 27m1 stop
Frontier Logo
11:51 am - 1:13 am
ORD
-
BOS
12h 22m1 stop
$128Frontier
Wed, Feb 4 - Tue, Feb 10
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$129JetBlue
Sat, Feb 7 - Sat, Feb 14
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$130JetBlue
Sat, Jan 17 - Fri, Jan 23
Southwest Logo
4:55 pm - 6:45 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$132Southwest
Sat, Jan 17 - Fri, Jan 23
Spirit Airlines Logo
7:00 am - 5:52 pm
BOS
-
ORD
11h 52m1 stop
Spirit Airlines Logo
10:48 am - 11:19 pm
ORD
-
BOS
11h 31m1 stop
$133Spirit Airlines
Sat, Jan 24 - Wed, Feb 4
Multiple Airlines Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
Multiple Airlines Logo
2:53 pm - 1:03 am
ORD
-
BOS
9h 10m1 stop
$134Multiple Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
Multiple Airlines Logo
5:15 am - 4:28 pm
ORD
-
BOS
10h 13m1 stop
$135Multiple Airlines
Wed, Jan 21 - Sat, Jan 24
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
9:40 am - 12:55 pm
MDW
-
BOS
2h 15mnonstop
$137Southwest
Sun, Jan 11 - Thu, Jan 15

United Airlines flights from Massachusetts to Chicago

Our best United Airlines deals on Massachusetts to Chicago flight tickets
United Airlines
Jan 17
BOS6:00 amBoston Logan Intl
3h 04m
ORD8:04 amChicago O'Hare Intl
Jan 17
ORD6:05 pmChicago O'Hare Intl
2h 33m
BOS9:38 pmBoston Logan Intl
$127
Find similar
United Airlines
Jan 1
BOS6:29 pmBoston Logan Intl
3h 06m
ORD8:35 pmChicago O'Hare Intl
Jan 7
ORD11:05 amChicago O'Hare Intl
2h 25m
BOS2:30 pmBoston Logan Intl
$132
Find similar
United Airlines
Jan 5
BOS6:01 amBoston Logan Intl
3h 04m
ORD8:05 amChicago O'Hare Intl
Jan 6
ORD6:05 pmChicago O'Hare Intl
2h 33m
BOS9:38 pmBoston Logan Intl
$147
Find similar

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets
Frontier
Feb 4
BOS6:00 amBoston Logan Intl
13h 27m
1 stop
ORD6:27 pmChicago O'Hare Intl
Feb 10
ORD11:51 amChicago O'Hare Intl
12h 22m
1 stop
BOS1:13 amBoston Logan Intl
$128
Find similar
Frontier
Jan 22
BOS6:00 amBoston Logan Intl
8h 37m
1 stop
ORD1:37 pmChicago O'Hare Intl
Feb 3
ORD2:53 pmChicago O'Hare Intl
9h 10m
1 stop
BOS1:03 amBoston Logan Intl
$145
Find similar
Frontier
Jan 8
BOS6:00 amBoston Logan Intl
6h 35m
1 stop
ORD11:35 amChicago O'Hare Intl
Jan 12
ORD4:49 pmChicago O'Hare Intl
7h 30m
1 stop
BOS1:19 amBoston Logan Intl
$162
Find similar

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 December 26, 2025.
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 - ORD

BOSORD

Boston Logan Intl

Sat 1/17

6:00 am-8:04 am

Nonstop3h 04m

Chicago O'Hare Intl

Sat 1/17

6:05 pm-9:38 pm

Nonstop2h 33m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/21

6:00 am-12:05 pm

1 stop7h 05m

Chicago Midway

Wed 1/28

1:20 pm-1:03 am

1 stop10h 43m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/4

6:00 am-6:27 pm

1 stop13h 27m

Chicago O'Hare Intl

Tue 2/10

11:51 am-1:13 am

1 stop12h 22m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/7

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sat 2/14

10:00 am-1:20 pm

Nonstop2h 20m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/23

7:45 am-11:10 am

Nonstop2h 25m

$130

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

4:55 pm-6:45 pm

Nonstop2h 50m

Chicago Midway

Fri 1/23

5:35 pm-8:50 pm

Nonstop2h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/24

7:00 am-5:52 pm

1 stop11h 52m

Chicago O'Hare Intl

Wed 2/4

10:48 am-11:19 pm

1 stop11h 31m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 1/27

2:53 pm-1:03 am

1 stop9h 10m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sat 1/24

5:15 am-4:28 pm

1 stop10h 13m

$135

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 1/11

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Thu 1/15

9:40 am-12:55 pm

Nonstop2h 15m

$137

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 $196.

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 $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 $418.

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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $352.

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 $251 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 $207 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

$137

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 $137. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $254.
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 $75Free CancellationRating
7.2
2,900 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,210 reviews
Search Spirit Airlines flights
DeltaPriceFrom $114Free CancellationRating
7.9
8,018 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,258 reviews
Search Southwest flights
United AirlinesPriceFrom $123Free CancellationRating
7.4
9,116 reviews
Search United Airlines flights
American AirlinesPriceFrom $129Free CancellationRating
7.2
11,068 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
Valparaiso
Schererville
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