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$70+ Cheap flights from Chicago (CHI) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Cheap flight deals from Chicago to Massachusetts

Cheapest flights from Chicago to Massachusetts
Explore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 23, 2026.

This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:34 pm
ORD
-
BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
-
ORD
1 stop12h 00m
Frontier
Deal found 3/20$140
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
-
BOS
1 stop12h 20m
Frontier
Wed 5/1312:01 pm
BOS
-
MDW
1 stop11h 01m
Frontier
Deal found 3/22$140
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Mon 5/116:00 am
BOS
-
MDW
1 stop6h 09m
Frontier
Deal found 3/20$141
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:00 pm
MDW
-
BOS
1 stop6h 30m
Southwest
Wed 5/2710:45 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/23$145
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:45 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Sat 5/169:25 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/22$146
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:50 pm
MDW
-
BOS
2 stops5h 50m
Southwest
Tue 6/95:35 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 3/22$151
This Cheapflightsfares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Sat 5/3011:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 3/20$152
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:11 pm
ORD
-
BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
-
ORD
Nonstop3h 12m
American Airlines
Deal found 3/21$153
This SmartFares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
-
ORD
Nonstop3h 03m
JetBlue
Deal found 3/20$154
This SmartFares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
-
ORD
Nonstop3h 03m
JetBlue
Deal found 3/18$155
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:56 pm
ORD
-
BOS
Nonstop2h 29m
American Airlines
Mon 5/47:40 pm
BOS
-
ORD
Nonstop3h 10m
American Airlines
Deal found 3/23$156
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:00 pm
ORD
-
BOS
Nonstop2h 35m
United Airlines
Sun 5/36:00 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 3/20$157

Find flight deals from Chicago to Massachusetts

Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Frontier)

One-way from

$70
(Frontier)

Popular in

April

Cheapest in

January

Average price

$225

Good round-trip deal

$167 or less

Good one-way deal

$88 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago (CHI) to Massachusetts
Search Deals
One-way flight from Chicago (CHI) to Massachusetts
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Massachusetts.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Massachusetts.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Massachusetts 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, Cheapflights users made 2,558,603 searches. Data last updated March 23, 2026.
Use the filters below to find and compare flights from Chicago to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 4/13

6:00 am-9:25 am

Nonstop2h 25m

Boston Logan Intl

Wed 4/15

6:00 am-7:59 am

Nonstop2h 59m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/30

7:00 am-10:35 am

Nonstop2h 35m

Boston Logan Intl

Wed 6/3

8:40 pm-10:35 pm

Nonstop2h 55m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 5/6

3:15 pm-6:35 pm

Nonstop2h 20m

Boston Logan Intl

Wed 5/13

7:20 am-9:05 am

Nonstop2h 45m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 8/20

7:00 am-10:28 am

Nonstop2h 28m

Boston Logan Intl

Tue 8/25

11:00 am-12:52 pm

Nonstop2h 52m

$157
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/7

9:25 am-12:40 pm

Nonstop2h 15m

Boston Logan Intl

Sat 5/9

3:30 pm-5:15 pm

Nonstop2h 45m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 6/3

12:50 pm-7:40 pm

2 stops5h 50m

Boston Logan Intl

Tue 6/9

5:50 am-10:45 am

1 stop5h 55m

$161

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/4

9:26 pm-12:59 am

Nonstop2h 33m

Boston Logan Intl

Sun 6/7

6:00 am-7:58 am

Nonstop2h 58m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 4/6

7:35 pm-11:02 pm

Nonstop2h 27m

Boston Logan Intl

Thu 4/9

7:15 am-9:25 am

Nonstop3h 10m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/5

4:00 pm-7:20 pm

Nonstop2h 20m

Boston Logan Intl

Mon 6/8

8:00 pm-12:15 am

1 stop5h 15m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/28

2:10 pm-11:10 pm

1 stop8h 00m

Boston Logan Intl

Sun 5/31

6:10 am-7:55 am

Nonstop2h 45m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Chicago to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Massachusetts

What is the cheapest month to book a flight from Chicago to Massachusetts?

Currently, September is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $91). Flying from Chicago to Massachusetts in January is currently the most expensive (average of $117). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MA?

Find hourly flight availability from Chicago to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 23, 2026.

One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 44% on airfare.

What is the cheapest day to fly from Chicago to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Massachusetts. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Massachusetts

Explore weekly flight availability from Chicago to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 23, 2026.

The most flights from CHI to USMA are scheduled on a Monday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated March 23, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,319 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,462 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,908 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,488 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Massachusetts?

    There are many flights that can get you from Chicago to Massachusetts in 2h 20m. Fly via United Airlines, Delta, or Southwest to get the fastest option. The distance between Chicago and Massachusetts is about 857 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Chicago to Massachusetts one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $58. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chicago to Massachusetts for a low price.

  • What are the most popular routes from Chicago to Massachusetts?

    When deciding which route to take from Chicago to Massachusetts consider Chicago O'Hare Intl - Boston Logan Intl, Chicago O'Hare Intl - Hartford Bradley Intl or Chicago Midway - Boston Logan Intl as they are the most popular.

  • What are the most reliable airlines from Chicago to Massachusetts?

    Before booking your flight to Massachusetts from Chicago, check out the most reliable airlines to get you to your destination on time: JetBlue (86%), TAP AIR PORTUGAL (79%), Hawaiian Airlines( 79%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $72. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $147 on average, our data indicates $603 when flying from Chicago to Massachusetts.

  • Can I find deals for flights from Chicago to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Chicago to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Massachusetts.

  • Can I find deals for business class flights from Chicago to Massachusetts?

    Yes. Cheapflights offers flight deals from Chicago to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Massachusetts?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $91). Flying from Chicago to Massachusetts in January is currently the most expensive (average of $117). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Massachusetts

Discover the top 6 airlines that operate flights from Chicago to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$62Average$365FlexibilityNo cancel feeOn-time62%
DeltaCheapest$86Average$253FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$91Average$158FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$117Average$247FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$379FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$124Average$244FlexibilityNo cancel feeOn-time63%

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