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Cheap flights from Massachusetts to Chicago from $92

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 6/3. 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.
Southwest Logo
5:20 am - 6:55 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$176Southwest
Sat, Jun 6 - Tue, Jun 9
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
$176JetBlue
Thu, Jun 4 - Mon, Jun 8
Frontier Logo
6:00 am - 11:12 am
BOS
-
MDW
6h 12m
1 stop
Frontier Logo
12:04 pm - 1:27 am
MDW
-
BOS
12h 23m
1 stop
$189Frontier
Tue, Aug 25 - Wed, Sep 2
Frontier Logo
9:12 am - 7:55 pm
BOS
-
ORD
11h 43m
1 stop
Frontier Logo
1:50 pm - 1:27 am
ORD
-
BOS
10h 37m
1 stop
$189Frontier
Tue, Aug 25 - Tue, Sep 1
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
9:30 am - 5:00 pm
ORD
-
ORH
6h 30m
1 stop
$220Delta
Tue, Aug 4 - Wed, Aug 12
Delta Logo
5:43 pm - 10:34 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
9:35 am - 5:03 pm
ORD
-
ORH
6h 28m
1 stop
$222Delta
Tue, Jun 9 - Wed, Jun 10
American Airlines Logo
5:18 pm - 7:10 am
ORH
-
ORD
14h 52m
1 stop
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
$232American Airlines
Mon, Jun 1 - Thu, Jun 4
American Airlines Logo
5:18 pm - 11:30 pm
ORH
-
ORD
7h 12m
2 stops
American Airlines Logo
6:04 am - 4:53 pm
ORD
-
ORH
9h 49m
2 stops
$235American Airlines
Wed, Jun 24 - Tue, Jun 30
Multiple Airlines Logo
12:24 pm - 11:05 pm
BDL
-
ORD
11h 41m
1 stop
Multiple Airlines Logo
5:27 pm - 11:59 pm
ORD
-
BDL
5h 32m
1 stop
$348Multiple Airlines
Wed, Jul 15 - Sat, Jul 18
Multiple Airlines Logo
7:11 pm - 11:19 pm
BDL
-
ORD
29h 08m
2 stops
Multiple Airlines Logo
5:13 pm - 11:32 am
ORD
-
BDL
17h 19m
1 stop
$351Multiple Airlines
Fri, Jul 3 - Tue, Jul 7

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets
JetBlue
Jun 4
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
Jun 8
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$176
JetBlue
Jun 3
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
Jun 10
ORD8:50 amChicago O'Hare Intl
2h 30m
BOS12:20 pmBoston Logan Intl
$182
JetBlue
Jun 6
BOS11:00 amBoston Logan Intl
2h 59m
ORD12:59 pmChicago O'Hare Intl
Jun 8
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$183

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets
Frontier
Aug 25
BOS9:12 amBoston Logan Intl
11h 43m
1 stop
ORD7:55 pmChicago O'Hare Intl
Sep 1
ORD1:50 pmChicago O'Hare Intl
10h 37m
1 stop
BOS1:27 amBoston Logan Intl
$189
Frontier
Jun 16
BOS9:10 amBoston Logan Intl
11h 40m
1 stop
ORD7:50 pmChicago O'Hare Intl
Jun 23
ORD1:29 pmChicago O'Hare Intl
10h 58m
1 stop
BOS1:27 amBoston Logan Intl
$190
Frontier
Jun 9
BOS9:10 amBoston Logan Intl
11h 43m
1 stop
ORD7:53 pmChicago O'Hare Intl
Jun 10
ORD6:55 amChicago O'Hare Intl
17h 32m
1 stop
BOS1:27 amBoston Logan Intl
$193

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 22, 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

Sat 6/6

5:20 am-6:55 am

Nonstop2h 35m

Chicago Midway

Tue 6/9

7:40 am-10:55 am

Nonstop2h 15m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/4

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 6/8

8:30 pm-11:59 pm

Nonstop2h 29m

$176

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 8/25

6:00 am-11:12 am

1 stop6h 12m

Chicago Midway

Wed 9/2

12:04 pm-1:27 am

1 stop12h 23m

$189

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/25

9:12 am-7:55 pm

1 stop11h 43m

Chicago O'Hare Intl

Tue 9/1

1:50 pm-1:27 am

1 stop10h 37m

$189

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 8/4

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Wed 8/12

9:30 am-5:00 pm

1 stop6h 30m

$220

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 6/9

5:43 pm-10:34 pm

1 stop5h 51m

Chicago O'Hare Intl

Wed 6/10

9:35 am-5:03 pm

1 stop6h 28m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/1

5:18 pm-7:10 am

1 stop14h 52m

Chicago O'Hare Intl

Thu 6/4

5:00 am-4:53 pm

1 stop10h 53m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 6/24

5:18 pm-11:30 pm

2 stops7h 12m

Chicago O'Hare Intl

Tue 6/30

6:04 am-4:53 pm

2 stops9h 49m

$235

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 7/15

12:24 pm-11:05 pm

1 stop11h 41m

Chicago O'Hare Intl

Sat 7/18

5:27 pm-11:59 pm

1 stop5h 32m

$348

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 7/3

7:11 pm-11:19 pm

2 stops29h 08m

Chicago O'Hare Intl

Tue 7/7

5:13 pm-11:32 am

1 stop17h 19m

$351

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 $168. 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 $205.

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 $318. 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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $365.

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 $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

$128

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 $128. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $238.
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

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
7.2
2,981 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,449 reviews
Search Delta flights
Spirit AirlinesPriceFrom $95Free CancellationRating
6.2
Search Spirit Airlines flights
United AirlinesPriceFrom $121Free CancellationRating
7.4
9,751 reviews
Search United Airlines flights
SouthwestPriceFrom $128Free CancellationRating
7.9
4,278 reviews
Search Southwest flights
American AirlinesPriceFrom $137Free CancellationRating
7.1
11,643 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
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