$64+ Cheap flights from O'Hare Intl (ORD) to Boston (BOS)
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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Feb 25 — Mar 41
1 adult, Economy
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Find cheap flights from O'Hare Intl to Boston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in September or January, booked 43 days in advance, depart on a Thursday or Wednesday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Boston
Cheapest flights from O'Hare Intl to BostonExplore the most affordable flight options available from O'Hare Intl to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.
Explore the most affordable flight options available from O'Hare Intl to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:42 pm
ORD
- BOS
1 stop6h 47m
Frontier
Tue 3/36:00 am
BOS
- ORD
1 stop11h 52m
Frontier
Deal found 1/23![Frontier logo]()
$131
This JetBlue deal was found by Cheapflights users on 1/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:04 am
ORD
- BOS
1 stop7h 20m
JetBlue
Sun 3/17:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 1/23![JetBlue logo]()
$132
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/317:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Tue 2/33:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 1/26![JetBlue logo]()
$133
This United Airlines deal was found by Cheapflights users on 1/26. 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 1/3011:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sun 2/16:00 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Deal found 1/26![United Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 1/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Wed 2/257:45 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 1/23![Delta logo]()
$136
This American Airlines deal was found by Cheapflights users on 1/25. 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 1/318:18 pm
ORD
- BOS
Nonstop2h 26m
American Airlines
Sun 2/16:10 am
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 1/25![American Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Sat 2/144:42 pm
ORD
- BOS
1 stop6h 47m
Multiple Airlines
Tue 2/175:50 pm
BOS
- ORD
1 stop16h 49m
Multiple Airlines
Deal found 1/24![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1112:36 pm
ORD
- BOS
1 stop11h 37m
Frontier
Wed 2/256:00 am
BOS
- ORD
1 stop11h 52m
Frontier
Deal found 1/23![Frontier logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 1/25. 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 3/1010:44 am
ORD
- BOS
1 stop10h 17m
Spirit Airlines
Wed 3/185:40 am
BOS
- ORD
1 stop13h 41m
Spirit Airlines
Deal found 1/25![Spirit Airlines logo]()
$140
This Booking.com deal was found by Cheapflights users on 1/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- BOS
1 stop9h 15m
Spirit Airlines
Tue 3/175:40 am
BOS
- ORD
1 stop13h 41m
Spirit Airlines
Deal found 1/24![Spirit Airlines logo]()
$141
This United Airlines deal was found by Cheapflights users on 1/24. 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 2/64:15 pm
ORD
- BOS
1 stop4h 37m
United Airlines
Sun 2/89:30 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Deal found 1/24![United Airlines logo]()
$142
This Flightnetwork deal was found by Cheapflights users on 1/25. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:15 am
ORD
- BOS
1 stop11h 00m
Spirit Airlines
Wed 3/185:40 am
BOS
- ORD
1 stop13h 41m
Spirit Airlines
Deal found 1/25![Spirit Airlines logo]()
$143
Find flight deals from O'Hare Intl to Boston
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 January 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (Kiwi.com) |
One-way from | $64 (Priceline) |
Popular in | February |
Cheapest in | September |
Average price | $207 |
Good round-trip deal | $165 or less |
Good one-way deal | $90 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Boston that are best for you.
Fly from
O'Hare Intl
Fly to
Boston
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 2/13
6:04 am-2:24 pm
1 stop7h 20m
Boston Logan Intl
Tue 2/24
7:00 am-9:10 am
Nonstop3h 10m
$132
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 3/10
7:30 am-10:50 am
Nonstop2h 20m
Boston Logan Intl
Tue 3/10
4:30 pm-6:35 pm
Nonstop3h 05m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/9
10:00 am-1:27 pm
Nonstop2h 27m
Boston Logan Intl
Mon 4/13
7:10 am-9:10 am
Nonstop3h 00m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 6/4
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
Tue 6/9
8:15 am-10:12 am
Nonstop2h 57m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/3
8:21 pm-11:56 pm
Nonstop2h 35m
Boston Logan Intl
Mon 6/8
6:50 am-8:45 am
Nonstop2h 55m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/8
10:10 am-1:40 pm
Nonstop2h 30m
Boston Logan Intl
Sat 7/11
8:10 pm-10:06 pm
Nonstop2h 56m
$156
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 6/4
8:21 pm-11:56 pm
Nonstop2h 35m
Boston Logan Intl
Mon 6/8
6:50 am-8:45 am
Nonstop2h 55m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 6/4
8:21 pm-11:56 pm
Nonstop2h 35m
Boston Logan Intl
Sun 6/7
6:00 am-7:55 am
Nonstop2h 55m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/3
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
Wed 6/3
2:15 pm-6:50 pm
1 stop5h 35m
$161
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 3/25
12:20 pm-9:25 pm
1 stop8h 05m
Boston Logan Intl
Mon 3/30
6:00 pm-10:56 pm
1 stop5h 56m
$167
Showing 1-10 of 21 results
Compare providers for flights from O'Hare Intl to Boston
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Boston in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from O'Hare Intl to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from O'Hare Intl 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 O'Hare Intl Airport to Boston
Prices
Airlines
Delays
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Boston?
Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Boston. Price data was last updated on January 23, 2026.
Booking 43 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Boston?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $91). Flying from Chicago O'Hare Intl Airport to Boston in February 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 ORD to BOS?
Find hourly flight availability from O'Hare Intl 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 January 26, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Boston?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Boston. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Tuesday evenings 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.
How often are flights from Chicago to Boston delayed?
About 23% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 153 minutes.
What is the most punctual flight time for Chicago to Boston flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Boston flights?
Over the last year, JetBlue have had the lowest number of delays on this route, with just 19% of flights being delayed.
The best insider tips for Chicago O'Hare Intl Airport to Boston flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago O'Hare Intl Airport to Boston trip
Our travel experts
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 January 26, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago O'Hare Intl Airport to Boston to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsMedford
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Waltham
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Alternative routes for O'Hare Intl to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from O'Hare Intl to Boston
Discover the top 6 airlines that operate flights from O'Hare Intl to Boston. 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 January 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$157 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$94 | Average$217 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$232 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$254 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |