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$88+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
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 May 12, 2026.

This American Airlines deal was found by Cheapflights users on 5/7. 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 5/306:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Sat 5/305:49 pm
BOS
-
ORD
Nonstop3h 15m
American Airlines
Deal found 5/7$167
This SmartFares deal was found by Cheapflights users on 5/10. 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.
Sat 5/301:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Sun 5/316:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/10$168
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
-
BOS
1 stop18h 27m
Frontier
Wed 6/106:00 am
BOS
-
MDW
1 stop17h 11m
Frontier
Deal found 5/12$169
This Cheapflightsfares deal was found by Cheapflights users on 5/8. 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.
Sat 5/301:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Tue 6/26:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/8$172
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Sat 5/307:45 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Tue 6/25:05 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/8$177
This Southwest deal was found by Cheapflights users on 5/8. 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.
Fri 5/297:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Wed 6/32:25 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 5/8$182
This Cheapflightsfares deal was found by Cheapflights users on 5/7. 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.
Tue 5/268:50 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Thu 5/286:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/7$186
This JetBlue deal was found by Cheapflights users on 5/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:50 am
ORD
-
BOS
Nonstop2h 32m
JetBlue
Wed 5/275:25 pm
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 5/11$187
This Southwest deal was found by Cheapflights users on 5/8. 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.
Fri 5/297:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Sun 5/316:10 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 5/8$187
This American Airlines deal was found by Cheapflights users on 5/9. 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 5/305:20 pm
ORD
-
BOS
Nonstop2h 33m
American Airlines
Sun 5/317:00 am
BOS
-
ORD
Nonstop3h 04m
American Airlines
Deal found 5/9$188
This Frontier deal was found by Cheapflights users on 5/11. 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 8/1912:04 pm
MDW
-
BOS
1 stop12h 23m
Frontier
Tue 8/256:00 am
BOS
-
MDW
1 stop6h 12m
Frontier
Deal found 5/11$190
This Frontier deal was found by Cheapflights users on 5/9. 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.
Tue 6/912:27 pm
MDW
-
BOS
1 stop12h 00m
Frontier
Tue 6/166:00 am
BOS
-
MDW
1 stop6h 12m
Frontier
Deal found 5/9$191

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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(American Airlines)

One-way from

$88
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$230

Good round-trip deal

$211 or less

Good one-way deal

$108 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. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 12, 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

Sat 7/4

7:10 am-10:46 am

Nonstop2h 36m

Boston Logan Intl

Sat 7/11

7:30 am-9:26 am

Nonstop2h 56m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/5

4:00 pm-7:20 pm

Nonstop2h 20m

Boston Logan Intl

Mon 6/8

6:45 pm-8:35 pm

Nonstop2h 50m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 6/2

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Wed 6/3

5:45 am-11:35 am

1 stop6h 50m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/16

1:00 pm-4:25 pm

Nonstop2h 25m

Boston Logan Intl

Thu 10/22

9:45 pm-11:25 pm

Nonstop2h 40m

$205

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 10/3

10:05 am-1:30 pm

Nonstop2h 25m

Boston Logan Intl

Mon 10/5

9:45 pm-11:25 pm

Nonstop2h 40m

$205

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 7/12

5:15 am-8:25 am

Nonstop2h 10m

Boston Logan Intl

Tue 7/14

3:45 pm-5:30 pm

Nonstop2h 45m

$207

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 6/6

5:25 am-8:40 am

Nonstop2h 15m

Boston Logan Intl

Fri 6/12

2:10 pm-7:10 pm

1 stop6h 00m

$211

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/26

5:20 pm-12:05 am

1 stop5h 45m

Boston Logan Intl

Mon 6/29

5:25 am-7:00 am

Nonstop2h 35m

$215

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/19

6:00 pm-11:25 pm

1 stop4h 25m

Boston Logan Intl

Mon 6/22

5:25 am-7:00 am

Nonstop2h 35m

$215

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 6/13

5:45 pm-9:05 pm

Nonstop2h 20m

Boston Logan Intl

Sun 9/13

9:05 pm-10:40 pm

Nonstop2h 35m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

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

How far ahead should I book a flight from Chicago to Massachusetts?

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Massachusetts. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $182). Flying from Chicago to Massachusetts in December is currently the most expensive (average of $283). 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 May 12, 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 46% 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 May 9, 2026.

Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon 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 May 12, 2026.

The most flights from CHI to USMA are scheduled on a Monday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

How much does it cost to fly round-trip from Chicago to Massachusetts?

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 May 12, 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
4,295 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
8,445 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
9,701 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
2,973 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
11,661 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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 Delta, Southwest, or American Airlines to get the fastest option. The distance between Chicago and Massachusetts is about 857 mi. This flight may include one or multiple stops.

  • 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 Midway - Boston Logan Intl or Chicago O'Hare Intl - Hartford Bradley 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: Avianca (94%), Icelandair (86%), TAP AIR PORTUGAL( 81%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $83. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $182 on average, our data indicates $439 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, November is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $182). Flying from Chicago to Massachusetts in December is currently the most expensive (average of $283). 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.

See more FAQs

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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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$68Average$414FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$87Average$328FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$122Average$258FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$126Average$249FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$127Average$301FlexibilityNo cancel feeOn-time71%

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