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Cheap flights from Massachusetts to Chicago from $95

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
12:45 pm - 2:30 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:25 pm - 9:40 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$216Southwest
Fri, Dec 11 - Tue, Dec 15
Southwest Logo
7:05 am - 8:50 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:25 pm - 9:45 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$216Southwest
Thu, Nov 12 - Mon, Nov 16
JetBlue Logo
6:55 am - 11:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 29m1 stop New York John F Kennedy Intl
JetBlue Logo
8:04 pm - 11:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 55mnonstop
$217JetBlue
Thu, Oct 8 - Tue, Oct 13
Frontier Logo
11:42 am - 6:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
7h 49m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 10:17 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
13h 33m1 stop Atlanta Hartsfield-Jackson
$218Frontier
Sat, Oct 24 - Mon, Oct 26
JetBlue Logo
4:10 pm - 10:00 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 50m1 stop New York John F Kennedy Intl
JetBlue Logo
7:05 am - 2:29 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
6h 24m1 stop New York John F Kennedy Intl
$221JetBlue
Mon, Oct 5 - Tue, Oct 6
Frontier Logo
11:42 am - 6:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
7h 49m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 10:17 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
13h 33m1 stop Atlanta Hartsfield-Jackson
$222Frontier
Sat, Oct 24 - Mon, Oct 26
Delta Logo
1:05 pm - 4:32 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
4h 27m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:30 pm - 12:20 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
5h 50m1 stop Minneapolis St Paul
$222Delta
Tue, Oct 27 - Mon, Nov 2
Delta Logo
6:00 pm - 10:17 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 17m1 stop New York LaGuardia
Delta Logo
7:00 am - 11:55 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
3h 55m1 stop Detroit Metropolitan Wayne County
$222Delta
Tue, Oct 27 - Sat, Oct 31
American Airlines Logo
12:56 pm - 5:29 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 33m1 stop Philadelphia
American Airlines Logo
6:00 am - 9:29 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 29mnonstop
$225American Airlines
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
12:29 pm - 4:50 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 21m1 stop New York John F Kennedy Intl
American Airlines Logo
6:00 am - 9:37 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 37mnonstop
$225American Airlines
Tue, Oct 6 - Tue, Oct 13

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JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets
JetBlue
Oct 8
BOS6:55 amBoston Logan Intl
5h 29m
1 stop
ORD11:24 amChicago O'Hare Intl
Oct 13
ORD8:04 pmChicago O'Hare Intl
2h 55m
BOS11:59 pmBoston Logan Intl
$217
JetBlue
Oct 5
BOS4:10 pmBoston Logan Intl
6h 50m
1 stop
ORD10:00 pmChicago O'Hare Intl
Oct 6
ORD7:05 amChicago O'Hare Intl
6h 24m
1 stop
BOS2:29 pmBoston Logan Intl
$221
JetBlue
Oct 16
BOS5:12 pmBoston Logan Intl
3h 02m
ORD7:14 pmChicago O'Hare Intl
Oct 19
ORD8:04 pmChicago O'Hare Intl
2h 55m
BOS11:59 pmBoston Logan Intl
$224

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets
Frontier
Oct 24
BOS11:42 amBoston Logan Intl
7h 49m
1 stop
ORD6:31 pmChicago O'Hare Intl
Oct 26
ORD7:44 pmChicago O'Hare Intl
13h 33m
1 stop
BOS10:17 amBoston Logan Intl
$218
Frontier
Nov 14
BOS11:27 amBoston Logan Intl
7h 49m
1 stop
ORD6:16 pmChicago O'Hare Intl
Nov 16
ORD7:50 pmChicago O'Hare Intl
14h 40m
1 stop
BOS11:30 amBoston Logan Intl
$227
Frontier
Nov 19
BOS12:39 pmBoston Logan Intl
12h 08m
1 stop
MDW11:47 pmChicago Midway
Nov 22
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$236

momondo Fare Finder

 
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 Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Fri 12/11

12:45 pm-2:30 pm

Nonstop2h 45m

Chicago Midway

Tue 12/15

6:25 pm-9:40 pm

Nonstop2h 15m

$216

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 11/12

7:05 am-8:50 am

Nonstop2h 45m

Chicago Midway

Mon 11/16

6:25 pm-9:45 pm

Nonstop2h 20m

$216

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 10/8

6:55 am-11:24 am

1 stop5h 29m

Chicago O'Hare Intl

Tue 10/13

8:04 pm-11:59 pm

Nonstop2h 55m

$217

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 10/24

11:42 am-6:31 pm

1 stop7h 49m

Chicago O'Hare Intl

Mon 10/26

7:44 pm-10:17 am

1 stop13h 33m

$218

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 10/5

4:10 pm-10:00 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 10/6

7:05 am-2:29 pm

1 stop6h 24m

$221

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 10/24

11:42 am-6:31 pm

1 stop7h 49m

Chicago O'Hare Intl

Mon 10/26

7:44 pm-10:17 am

1 stop13h 33m

$222

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/27

1:05 pm-4:32 pm

1 stop4h 27m

Chicago O'Hare Intl

Mon 11/2

5:30 pm-12:20 am

1 stop5h 50m

$222

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/27

6:00 pm-10:17 pm

1 stop5h 17m

Chicago O'Hare Intl

Sat 10/31

7:00 am-11:55 am

1 stop3h 55m

$222

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 11/7

12:56 pm-5:29 pm

1 stop5h 33m

Chicago O'Hare Intl

Wed 11/11

6:00 am-9:29 am

Nonstop2h 29m

$225

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/6

12:29 pm-4:50 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 10/13

6:00 am-9:37 am

Nonstop2h 37m

$225

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 $323. 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 $422.

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 $286. 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 $262 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.

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

$95

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 $95. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $216.
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 $72Free CancellationRating
7.1
3,037 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.8
8,567 reviews
Search Delta flights
United AirlinesPriceFrom $132Free CancellationRating
7.4
10,209 reviews
Search United Airlines flights
SouthwestPriceFrom $139Free CancellationRating
8.0
4,188 reviews
Search Southwest flights
American AirlinesPriceFrom $143Free CancellationRating
7.1
12,055 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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport