Cheap flights from Massachusetts to Chicago (CHI) from $50
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 5/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
BOS — CHI
May 7 — May 141
From?
To?
1 adult, Economy
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How far in advance should I book a flight from Massachusetts to Chicago?
Users have found that booking a flight from Massachusetts to Chicago at least 55 days early can save you up to 24% on average compared to booking a flight this week. If booking 55 days before your flight isn’t an option for you, users have found flights from Massachusetts to Chicago for as little as $237 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $310 for flights departing within the next 3 days.
What is the cheapest month to fly from Massachusetts to Chicago?
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Massachusetts in January are about $260 on average during January, but can be found for as low as $79.
When is the cheapest time to fly from Massachusetts to Chicago (MA - CHI)?
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.
Cheap Spirit Airlines flights from Massachusetts to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between Massachusetts and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
Take a look at some of the lowest-priced Spirit Airlines flights heading from Massachusetts to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
Tue 5/710:16 amBOS - ORD
1 stop10h 53mSpirit Airlines
Wed 5/87:00 amORD - BOS
1 stop7h 13mSpirit Airlines
Deal found 4/30$88
Tue 5/711:49 amBOS - ORD
1 stop21h 56mSpirit Airlines
Tue 5/146:40 pmORD - BOS
2 stops28h 15mSpirit Airlines
Deal found 4/30$94
Tue 5/71:06 pmBOS - ORD
1 stop8h 03mSpirit Airlines
Wed 5/157:20 amORD - BOS
1 stop13h 16mSpirit Airlines
Deal found 4/30$95
Sat 5/1112:23 pmBOS - ORD
1 stop12h 06mSpirit Airlines
Tue 5/289:15 pmORD - BOS
2 stops25h 11mSpirit Airlines
Deal found 5/1$102
Tue 5/711:12 amBOS - ORD
2 stops14h 08mSpirit Airlines
Wed 5/87:00 amORD - BOS
1 stop7h 13mSpirit Airlines
Deal found 4/30$104
Tue 5/73:16 pmBOS - ORD
2 stops19h 39mSpirit Airlines
Tue 5/149:15 pmORD - BOS
2 stops25h 40mSpirit Airlines
Deal found 4/30$106
Tue 5/710:16 amBOS - ORD
1 stop10h 53mSpirit Airlines
Wed 5/158:09 pmORD - BOS
2 stops24h 28mSpirit Airlines
Deal found 4/30$108
Sat 5/1110:27 pmBOS - ORD
1 stop14h 07mSpirit Airlines
Tue 5/149:15 pmORD - BOS
2 stops16h 07mSpirit Airlines
Deal found 4/30$109
Sat 5/1112:23 pmBOS - ORD
1 stop12h 06mSpirit Airlines
Tue 5/149:35 amORD - BOS
1 stop24h 03mSpirit Airlines
Deal found 5/1$110
Cheap American Airlines flights from Massachusetts to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between Massachusetts and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
Some of the lowest-priced American Airlines flights we've found at this time heading from Massachusetts to Chicago. Deals are refreshing constantly so come back soon for more options.
Tue 5/285:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Fri 5/316:55 pmORD - BOS
Nonstop2h 30mAmerican Airlines
Deal found 4/30$163
Tue 5/285:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Sat 6/18:39 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/1$182
Tue 5/285:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Fri 5/313:20 pmORD - BOS
1 stop4h 40mAmerican Airlines
Deal found 4/30$200
Wed 5/225:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Sun 5/266:30 amORD - BOS
1 stop4h 44mAmerican Airlines
Deal found 5/1$201
Sat 6/297:30 pmBOS - ORD
Nonstop2h 56mAmerican Airlines
Wed 7/35:07 amORD - BOS
1 stop4h 05mAmerican Airlines
Deal found 4/30$210
Wed 5/84:54 pmBOS - ORD
1 stop5h 35mAmerican Airlines
Tue 5/148:29 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 4/30$217
Thu 5/95:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Mon 5/138:29 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/1$218
Fri 5/105:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Tue 5/148:29 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/1$229
Thu 5/95:30 amBOS - ORD
1 stop4h 28mAmerican Airlines
Mon 5/138:29 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 4/30$233
Cheap Massachusetts to Chicago flights in May & June 2024
Find cheap flight options from Massachusetts to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,899,487 searches. Prices were last updated on May 2, 2024.
These are some of the most attractive deals on flights from Massachusetts to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Sat 5/2512:59 pmBOS - MDW
1 stop7h 58mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 4/30$98
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/30$99
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/30$103
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/30$105
Sat 5/2512:59 pmBOS - MDW
1 stop7h 58mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/1$109
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 43mFrontier
Deal found 4/30$113
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sun 5/197:49 amMDW - BOS
1 stop24h 15mFrontier
Deal found 5/1$121
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Thu 5/167:49 amMDW - BOS
1 stop24h 15mFrontier
Deal found 4/30$123
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sun 5/197:49 amMDW - BOS
1 stop24h 15mFrontier
Deal found 5/1$125
Massachusetts to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Massachusetts and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
These are some of the most attractive deals on flights from Massachusetts to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Sat 5/2512:59 pmBOS - MDW
1 stop7h 58mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 4/30$98
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/30$99
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/30$103
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/30$105
Sat 5/2512:59 pmBOS - MDW
1 stop7h 58mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/1$109
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 43mFrontier
Deal found 4/30$113
Sat 6/810:12 amBOS - MDW
1 stop24h 21mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 43mFrontier
Deal found 4/30$114
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sun 5/197:49 amMDW - BOS
1 stop24h 15mFrontier
Deal found 5/1$121
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Thu 5/167:49 amMDW - BOS
1 stop24h 15mFrontier
Deal found 4/30$123
Non-stop flights to Chicago from Massachusetts
Discover non-stop flight options from Massachusetts to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
For a quicker trip, book one of these direct flights from Massachusetts to Chicago. Users can also choose from other Massachusetts to Chicago flights by using the search form above.
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/30$62
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 5/1$63
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 5/1$67
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Sat 6/88:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/30$72
Thu 6/66:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/30$73
Thu 6/66:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Thu 6/139:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/30$74
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/30$75
Thu 6/66:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/30$84
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/29$85
Massachusetts to Chicago flights leaving soon
Find last-minute flight options from Massachusetts to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
Check out these flights departing soon from Massachusetts to Chicago. Users should be sure to double check the price, date, and time of their last-minute flight.
Tue 5/710:16 amBOS - ORD
1 stop10h 53mSpirit Airlines
Wed 5/87:00 amORD - BOS
1 stop7h 13mSpirit Airlines
Deal found 4/30$88
Tue 5/711:49 amBOS - ORD
1 stop21h 56mSpirit Airlines
Tue 5/146:40 pmORD - BOS
2 stops28h 15mSpirit Airlines
Deal found 4/30$94
Tue 5/71:06 pmBOS - ORD
1 stop8h 03mSpirit Airlines
Wed 5/157:20 amORD - BOS
1 stop13h 16mSpirit Airlines
Deal found 4/30$95
Sat 5/1112:23 pmBOS - ORD
1 stop12h 06mMultiple Airlines
Sat 5/185:56 pmORD - BOS
1 stop14h 47mMultiple Airlines
Deal found 5/1$98
Sat 5/1112:23 pmBOS - ORD
1 stop12h 06mSpirit Airlines
Tue 5/289:15 pmORD - BOS
2 stops25h 11mSpirit Airlines
Deal found 5/1$102
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/30$103
Tue 5/711:12 amBOS - ORD
2 stops14h 08mSpirit Airlines
Wed 5/87:00 amORD - BOS
1 stop7h 13mSpirit Airlines
Deal found 4/30$104
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/30$105
Tue 5/73:16 pmBOS - ORD
2 stops19h 39mSpirit Airlines
Tue 5/149:15 pmORD - BOS
2 stops25h 40mSpirit Airlines
Deal found 4/30$106
One-way flights to Chicago from Massachusetts
Search for one-way flight options from Massachusetts to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
Users traveling one-way from Massachusetts to Chicago can select one of these great deals. For those needing a return trip from Massachusetts, there is a search form available above.
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 5/1$50
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/30$56
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/30$57
Wed 6/57:49 amBOS - MDW
1 stop6h 38mFrontier
Deal found 4/30$58
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/30$59
Sat 5/1811:29 amBOS - MDW
2 stops9h 44mFrontier
Deal found 4/30$60
Sat 5/1112:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 4/29$64
Sat 6/810:12 amBOS - MDW
1 stop24h 19mFrontier
Deal found 5/1$68
Sat 6/810:12 amBOS - MDW
1 stop24h 21mFrontier
Deal found 4/30$69
Find flights from Massachusetts to Chicago within your budget
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, Cheapflights users made 2,899,487 searches. Data last updated May 2, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$98 - $204
Route
Depart
Return
Price
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/25
1 stop7h 58m
Chicago Midway
Wed 5/29
1 stop23h 51m
$98
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/15
1 stop11h 44m
Chicago Midway
Sat 5/18
1 stop11h 35m
$99
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/11
1 stop11h 19m
Chicago Midway
Sat 5/18
1 stop11h 35m
$103
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/5
2 stops17h 07m
Chicago O'Hare Intl
Fri 6/7
1 stop10h 36m
$140
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/25
1 stop6h 00m
Chicago O'Hare Intl
Tue 5/28
1 stop5h 24m
$145
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/28
Nonstop2h 56m
Chicago O'Hare Intl
Fri 5/31
Nonstop2h 30m
$163
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/22
Nonstop2h 54m
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 26m
$167
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/22
Nonstop2h 53m
Chicago O'Hare Intl
Sat 5/25
1 stop5h 04m
$191
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/10
Nonstop2h 55m
Chicago O'Hare Intl
Tue 5/14
Nonstop2h 36m
$204
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 2, 2024.
Read through reviews of airlines operating flights from Massachusetts to Chicago, such as Spirit Airlines, American Airlines and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
6,121 reviews
Food
7.3
Crew
8.7
Entertainment
7.8
Comfort
8.1
Boarding
8.3
Overall
8.2
Reviews
1 / 10
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Southwest
6,121 reviews
Southwest
6,121 reviews
Food
7.3
Crew
8.7
Entertainment
7.8
Comfort
8.1
Boarding
8.3
Overall
8.2
Reviews
1 / 10
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
9,115 reviews
Southwest
6,121 reviews
Food
7.3
Crew
8.7
Entertainment
7.8
Comfort
8.1
Boarding
8.3
Overall
8.2
Reviews
1 / 10
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
10,874 reviews
Southwest
6,121 reviews
Food
7.3
Crew
8.7
Entertainment
7.8
Comfort
8.1
Boarding
8.3
Overall
8.2
Reviews
1 / 10
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
4,561 reviews
Southwest
6,121 reviews
Food
7.3
Crew
8.7
Entertainment
7.8
Comfort
8.1
Boarding
8.3
Overall
8.2
Reviews
1 / 10
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
435 reviews
Southwest
6,121 reviews
Food
7.3
Crew
8.7
Entertainment
7.8
Comfort
8.1
Boarding
8.3
Overall
8.2
Reviews
1 / 10
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Massachusetts to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Massachusetts to Chicago
Discover the top 7 airlines that operate flights from Massachusetts to Chicago. 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 2,899,487 searches. Data last updated May 2, 2024.
Search flights from Massachusetts to Chicago by cabin class
Find flights from Massachusetts to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Massachusetts to Chicago
Find hourly flight availability from Massachusetts to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 2, 2024.
| 3%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 38%of flight departures | Morning6 am to noon |
| 55%of flight departures | AfternoonNoon to 6 pm |
| 4%of flight departures | Evening6 pm to midnight |
Midnight
6 AM
Noon
6 PM
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
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How does Cheapflights help users find flights from Massachusetts to Chicago?
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Why should you use Cheapflights to find cheap flight tickets from Massachusetts to Chicago?
Cheapflights simply makes it quick and affordable to book flights from Massachusetts to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Massachusetts to Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Massachusetts to Chicago flexibly with Cheapflights today.
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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!