Latest deals
Insights
FAQs
Reviews
Price Alerts

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 11/18. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 6:04 pmBOS-MDW
13h 04m1 stop
Frontier Logo
8:00 am - 12:01 amMDW-BOS
15h 01m1 stop
$121Frontier
Find Deal
Thu, Dec 4 - Tue, Dec 9
Frontier Logo
6:00 am - 6:04 pmBOS-MDW
13h 04m1 stop
Frontier Logo
6:00 am - 12:44 amMDW-BOS
17h 44m1 stop
$123Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
5:20 am - 7:00 amBOS-MDW
2h 40mnonstop
Southwest Logo
5:45 am - 11:50 amMDW-BOS
5h 05m1 stop
$127Southwest
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
7:30 am - 9:35 amBOS-ORD
3h 05mnonstop
Delta Logo
10:35 am - 2:03 pmORD-BOS
2h 28mnonstop
$127Delta
Find Deal
Sun, Nov 16 - Tue, Nov 18
JetBlue Logo
7:09 am - 9:22 amBOS-ORD
3h 13mnonstop
JetBlue Logo
7:15 am - 10:34 amORD-BOS
2h 19mnonstop
$129JetBlue
Find Deal
Thu, Oct 23 - Sun, Oct 26
Multiple Airlines Logo
3:00 pm - 1:03 amBOS-ORD
11h 03m1 stop
Multiple Airlines Logo
7:06 pm - 7:16 pmORD-BOS
23h 10m1 stop
$130Multiple Airlines
Find Deal
Wed, Oct 29 - Thu, Oct 30
Southwest Logo
5:20 am - 7:00 amBOS-MDW
2h 40mnonstop
Southwest Logo
1:25 pm - 9:10 pmMDW-BOS
6h 45m2 stops
$132Southwest
Find Deal
Sat, Oct 25 - Wed, Oct 29
JetBlue Logo
7:09 am - 9:22 amBOS-ORD
3h 13mnonstop
JetBlue Logo
6:45 am - 3:00 pmORD-BOS
7h 15m1 stop
$132JetBlue
Find Deal
Thu, Oct 23 - Fri, Oct 31
Delta Logo
7:20 am - 9:22 amBOS-ORD
3h 02mnonstop
Delta Logo
7:05 am - 10:29 amORD-BOS
2h 24mnonstop
$137Delta
Find Deal
Thu, Oct 23 - Thu, Oct 30
Multiple Airlines Logo
2:15 pm - 9:33 pmBOS-ORD
8h 18m1 stop
Multiple Airlines Logo
5:45 pm - 10:00 amORD-BOS
15h 15m1 stop
$143Multiple Airlines
Find Deal
Wed, Oct 29 - Sat, Nov 1

American Airlines flights from Massachusetts to Chicago

Our best American Airlines deals on Massachusetts to Chicago flight tickets
American Airlines
Oct 15
BOS5:24 amBoston Logan Intl
3h 01m
ORD7:25 amChicago O'Hare Intl
Oct 20
ORD8:25 pmChicago O'Hare Intl
2h 29m
BOS11:54 pmBoston Logan Intl
$137
Find similar
American Airlines
Nov 20
BOS6:45 amBoston Logan Intl
3h 07m
ORD8:52 amChicago O'Hare Intl
Nov 24
ORD3:03 pmChicago O'Hare Intl
2h 21m
BOS6:24 pmBoston Logan Intl
$141
Find similar
American Airlines
Nov 14
BOS7:19 pmBoston Logan Intl
3h 06m
ORD9:25 pmChicago O'Hare Intl
Nov 18
ORD3:08 pmChicago O'Hare Intl
2h 21m
BOS6:29 pmBoston Logan Intl
$145
Find similar

United Airlines flights from Massachusetts to Chicago

Our best United Airlines deals on Massachusetts to Chicago flight tickets
United Airlines
Oct 24
BOS3:17 pmBoston Logan Intl
2h 50m
ORD5:07 pmChicago O'Hare Intl
Oct 27
ORD6:15 amChicago O'Hare Intl
2h 15m
BOS9:30 amBoston Logan Intl
$133
Find similar
United Airlines
Oct 30
BOS9:40 amBoston Logan Intl
3h 00m
ORD11:40 amChicago O'Hare Intl
Oct 31
ORD10:48 amChicago O'Hare Intl
2h 21m
BOS2:09 pmBoston Logan Intl
$134
Find similar
United Airlines
Oct 16
BOS6:00 amBoston Logan Intl
2h 56m
ORD7:56 amChicago O'Hare Intl
Oct 16
ORD1:30 pmChicago O'Hare Intl
2h 32m
BOS5:02 pmBoston Logan Intl
$135
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 October 9, 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 - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

6:00 am-6:04 pm

1 stop13h 04m

Chicago Midway

Tue 12/9

8:00 am-12:01 am

1 stop15h 01m

$121

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

6:00 am-6:04 pm

1 stop13h 04m

Chicago Midway

Mon 12/8

6:00 am-12:44 am

1 stop17h 44m

$123

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Tue 10/28

5:45 am-11:50 am

1 stop5h 05m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 11/16

7:30 am-9:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Tue 11/18

10:35 am-2:03 pm

Nonstop2h 28m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Sun 10/26

7:15 am-10:34 am

Nonstop2h 19m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/29

3:00 pm-1:03 am

1 stop11h 03m

Chicago O'Hare Intl

Thu 10/30

7:06 pm-7:16 pm

1 stop23h 10m

$130

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Wed 10/29

1:25 pm-9:10 pm

2 stops6h 45m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Fri 10/31

6:45 am-3:00 pm

1 stop7h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

7:20 am-9:22 am

Nonstop3h 02m

Chicago O'Hare Intl

Thu 10/30

7:05 am-10:29 am

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/29

2:15 pm-9:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Sat 11/1

5:45 pm-10:00 am

1 stop15h 15m

$143

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $197.

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 $321. 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 $434.

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 $273. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

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 $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

$128

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

2 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 $206.
The fastest flight from Massachusetts to Chicago takes 2h 10m
Direct flights go from Massachusetts to Chicago every day.
There are 2 airports near Chicago: 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
Spirit AirlinesPriceFrom $69Free CancellationRating
6.3
8,088 reviews
Search Spirit Airlines flights
JetBluePriceFrom $85Free CancellationRating
7.2
2,908 reviews
Search JetBlue flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,143 reviews
Search Frontier flights
DeltaPriceFrom $112Free CancellationRating
7.9
7,969 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,237 reviews
Search Southwest flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
8,968 reviews
Search United Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
11,043 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
Schererville
Valparaiso
Crown Point
Munster
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/8
Sat 11/15
By creating a price alert you accept our terms of use and privacy policy.

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