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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
23 Jul — 30 Jul1
Return
1 adult
Economy
Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or August, booked 73 days in advance, depart on a Saturday or Monday and return on a Thursday
Cheap flight deals from Chicago to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 18 July 2025.
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 July 2025.
Fri 8/816:25ORD - BOS
Nonstop2h 35mJetBlue
Mon 11/806:00BOS - ORD
Nonstop2h 55mJetBlue
Deal found 18/7£102
Wed 3/915:10ORD - BOS
1 stop6h 20mSouthwest
Thu 4/907:30BOS - ORD
2 stops11h 25mSouthwest
Deal found 16/7£106
Wed 6/820:05ORD - BOS
Nonstop2h 27mUnited Airlines
Tue 12/819:04BOS - ORD
1 stop5h 37mUnited Airlines
Deal found 17/7£107
Sat 16/807:00ORD - BOS
Nonstop2h 29mDelta
Wed 20/819:55BOS - ORD
Nonstop2h 59mDelta
Deal found 18/7£116
Wed 30/710:00ORD - BOS
1 stop8h 30mSpirit Airlines
Sat 2/820:39BOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 16/7£125
Wed 30/718:20ORD - BOS
Nonstop2h 39mMultiple Airlines
Sat 2/820:39BOS - ORD
1 stop13h 16mMultiple Airlines
Deal found 16/7£151
Best flights from Chicago to Boston
Discover carefully curated flight deals from Chicago to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 18 July 2025.
Fri 8/816:25ORD - BOS
Nonstop2h 35mJetBlue
Mon 11/806:00BOS - ORD
Nonstop2h 55mJetBlue
Deal found 18/7£102
Wed 3/915:10ORD - BOS
1 stop6h 20mSouthwest
Thu 4/907:30BOS - ORD
2 stops11h 25mSouthwest
Deal found 16/7£106
Wed 6/820:05ORD - BOS
Nonstop2h 27mUnited Airlines
Tue 12/819:04BOS - ORD
1 stop5h 37mUnited Airlines
Deal found 17/7£107
Sat 16/807:00ORD - BOS
Nonstop2h 29mDelta
Wed 20/819:55BOS - ORD
Nonstop2h 59mDelta
Deal found 18/7£116
Wed 30/710:00ORD - BOS
1 stop8h 30mSpirit Airlines
Sat 2/820:39BOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 16/7£125
Wed 30/718:20ORD - BOS
Nonstop2h 39mMultiple Airlines
Sat 2/820:39BOS - ORD
1 stop13h 16mMultiple Airlines
Deal found 16/7£151
Direct flights from Chicago to Boston
Explore direct flight options from Chicago to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated 18 July 2025.
Fri 8/816:25ORD - BOS
Nonstop2h 35mJetBlue
Wed 13/806:00BOS - ORD
Nonstop2h 55mJetBlue
Deal found 16/7£102
Mon 4/821:32ORD - BOS
Nonstop2h 27mUnited Airlines
Tue 5/806:07BOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 17/7£110
Sat 16/807:00ORD - BOS
Nonstop2h 29mDelta
Sat 23/807:20BOS - ORD
Nonstop2h 55mDelta
Deal found 17/7£116
Sat 30/820:25ORD - BOS
Nonstop2h 34mAmerican Airlines
Sat 6/914:45BOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 16/7£123
Last-minute flights from Chicago to Boston
Discover last-minute flight deals from Chicago to Boston. Data last updated 18 July 2025 and is based on user searches.
Fri 25/716:27ORD - BOS
Nonstop2h 33mJetBlue
Mon 28/706:00BOS - ORD
Nonstop2h 55mJetBlue
Deal found 18/7£102
Fri 25/716:00ORD - BOS
1 stop7h 05mSouthwest
Tue 29/705:00BOS - ORD
1 stop8h 45mSouthwest
Deal found 16/7£121
Sun 27/721:32ORD - BOS
Nonstop2h 27mUnited Airlines
Thu 7/807:45BOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 17/7£142
Mon 28/707:00ORD - BOS
Nonstop2h 31mDelta
Fri 1/812:00BOS - ORD
1 stop7h 49mDelta
Deal found 17/7£169
Mon 28/720:30ORD - BOS
Nonstop2h 44mAmerican Airlines
Thu 31/705:00BOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 17/7£198
Wed 30/710:00ORD - BOS
1 stop8h 30mSpirit Airlines
Sat 2/820:39BOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 16/7£125
Wed 30/718:20ORD - BOS
Nonstop2h 39mMultiple Airlines
Sat 2/820:39BOS - ORD
1 stop13h 16mMultiple Airlines
Deal found 16/7£151
Wed 6/807:30ORD - BOS
Nonstop2h 27mUnited Airlines
Tue 12/819:04BOS - ORD
1 stop5h 37mUnited Airlines
Deal found 17/7£107
Fri 8/816:25ORD - BOS
Nonstop2h 35mJetBlue
Wed 13/806:00BOS - ORD
Nonstop2h 55mJetBlue
Deal found 16/7£102
Sat 16/807:00ORD - BOS
Nonstop2h 29mDelta
Wed 20/819:55BOS - ORD
Nonstop2h 59mDelta
Deal found 18/7£116
Sat 30/813:30ORD - BOS
1 stop7h 45mSouthwest
Wed 3/905:40BOS - ORD
1 stop7h 10mSouthwest
Deal found 16/7£106
One-way flights from Chicago to Boston
Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated 18 July 2025.
Mon 25/808:40ORD - BOS
Nonstop2h 24mJetBlue
Deal found 18/7£51
Tue 9/911:48ORD - BOS
1 stop11h 07mSpirit Airlines
Deal found 18/7£52
Wed 22/1013:10ORD - BOS
1 stop5h 44mUnited Airlines
Deal found 17/7£55
Sat 9/814:55ORD - BOS
1 stop5h 00mSouthwest
Deal found 17/7£58
Sun 24/807:00ORD - BOS
Nonstop2h 29mDelta
Deal found 18/7£65
Mon 25/806:06ORD - BOS
1 stop5h 19mAmerican Airlines
Deal found 16/7£94
Tue 25/1111:42ORD - BOS
1 stop20h 41mSun Country Air
Deal found 18/7£101
Cheapflights Fare Finder
Customise your flight search to find flights from Chicago to Boston 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 858,174 searches. Data last updated 18 July 2025.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.
Fly from
Chicago
Fly to
Boston
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/8
16:25-20:00
Nonstop2h 35m
Boston Logan Intl
Wed 13/8
06:00-07:55
Nonstop2h 55m
£102
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 3/9
15:10-22:30
1 stop6h 20m
Boston Logan Intl
Thu 4/9
07:30-17:55
2 stops11h 25m
£106
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/8
20:05-23:32
Nonstop2h 27m
Boston Logan Intl
Tue 12/8
19:04-23:41
1 stop5h 37m
£107
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 16/8
07:00-10:29
Nonstop2h 29m
Boston Logan Intl
Wed 20/8
19:55-21:54
Nonstop2h 59m
£116
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 30/7
10:00-19:30
1 stop8h 30m
Boston Logan Intl
Sat 2/8
20:39-08:55
1 stop13h 16m
£125
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 30/7
18:20-21:59
Nonstop2h 39m
Boston Logan Intl
Sat 2/8
20:39-08:55
1 stop13h 16m
£151
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 25/8
08:40-12:04
Nonstop2h 24m
£51
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/9
11:48-23:55
1 stop11h 07m
£52
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 22/10
13:10-19:54
1 stop5h 44m
£55
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/8
14:55-20:55
1 stop5h 00m
£58
Flights are sorted by cheapest return flights first.
Deals found on 18/7
Showing 1-10 of 13 results
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Best time to book a flight from Chicago to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.
Estimated return 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 Boston
How far ahead should I book a flight from Chicago to Boston?
Use this chart to determine the optimal time to book a return flight from Chicago to Boston. Price data was last updated on 11 July 2025.
Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. 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 Boston?
Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). 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 BOS?
Find hourly flight availability from Chicago to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 18 July 2025.
When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight at midday, which can drop the price by up to 68% versus a flight in the afternoon.
Weekly flight availability from Chicago to Boston
Explore weekly flight availability from Chicago to Boston. 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 18 July 2025.
The most flights from CHI to BOS are scheduled on a Thursday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).
How much does it cost for a return flight from Chicago to Boston?
Reviews of airlines servicing Boston
Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated 18 July 2025.
Read reviews from past customers who have flown with Southwest, Delta, andUnited Airlines
from Chicago to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
It’s southwest so no frills but clean, efficient and got me to my location.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
What airport do you fly into for flights to Boston from Chicago?
Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 62 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.
What are the cheapest airlines flying from Chicago to Boston round-trip?
Flying on JetBlue is currently your cheapest option to Boston, with prices starting at £102. Additional return tickets that might be worth considering are offered by Southwest and United Airlines, with the lowest prices starting at £106 and £107, respectively. You may be able to fly from Chicago to Boston for 39% less than the average price by searching for these airlines.
What are the cheapest airlines to fly from Chicago to Boston one-way?
One-way options have recently been found by users for as low as £51 on JetBlue. Other airlines that offer cheap prices include Spirit Airlines from £52 and United Airlines from £55 one-way.
What are the most reliable airlines from Chicago to Boston?
No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Etihad Airways (93%), Envoy Air (78%) or EL AL (77%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Chicago to Boston?
The cheapest flight price from Chicago to Boston is £77. On average you can expect to pay £455. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £134.
Can I find deals for business class flights from Chicago to Boston?
Yes. Cheapflights offers flight deals from Chicago to Boston 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 Boston?
Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). 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.
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Chicago to Boston?
Deals for Chicago to Boston flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Boston.
Can Cheapflights find flights from Chicago to Boston with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Boston, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?
Yes! Start tracking prices for Chicago to Boston flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.
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