American Airlines' Main Cabin Extra offers more legroom, enhancing comfort on short domestic flights.
American Airlines provides priority boarding with Main Cabin Extra, saving time for business travelers.
$79+ Cheap flights from Chicago (CHI) 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Feb 4 — Feb 111
1 adult, Economy
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Find cheap flights from Chicago 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.The best prices from Chicago to Boston Logan Intl are usually found in September or August, booked 83 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
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 January 30, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $146 (Kiwi.com) |
One-way from | $79 (Delta) |
Popular in | April |
Cheapest in | September |
Average price | $227 |
Good round-trip deal | $193 or less |
Good one-way deal | $108 or less |
Find flight deals from Chicago to Boston
Cheapest flights from Chicago to BostonExplore 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 January 30, 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 January 30, 2025.
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 5/24:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Tue 5/134:35 pmBOS - ORD
1 stop6h 53mMultiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$146
This Trip.com deal was found by Cheapflights users on 1/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/14:19 pmMDW - BOS
1 stop7h 11mFrontier
Fri 3/75:10 amBOS - MDW
1 stop7h 24mFrontier
Deal found 1/29![Frontier logo]()
$146
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/127:07 amORD - BOS
2 stops14h 34mSpirit Airlines
Tue 2/188:10 pmBOS - ORD
1 stop16h 40mSpirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$147
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/710:00 amORD - BOS
1 stop13h 44mFrontier
Tue 3/116:00 amBOS - ORD
1 stop29h 57mFrontier
Deal found 1/29![Frontier logo]()
$149
This Delta deal was found by Cheapflights users on 1/29. 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.
Thu 2/207:10 amORD - BOS
Nonstop2h 33mDelta
Tue 2/2511:45 amBOS - ORD
Nonstop3h 01mDelta
Deal found 1/29![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 1/29. 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 2/2610:05 amMDW - BOS
Nonstop2h 15mSouthwest
Fri 2/287:45 pmBOS - MDW
Nonstop2h 50mSouthwest
Deal found 1/29![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 1/29. 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.
Sun 2/168:05 amORD - BOS
Nonstop2h 14mAmerican Airlines
Thu 2/206:34 amBOS - ORD
Nonstop3h 05mAmerican Airlines
Deal found 1/29![American Airlines logo]()
$168
This JetBlue deal was found by Cheapflights users on 1/29. 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.
Sat 3/14:50 pmORD - BOS
Nonstop2h 24mJetBlue
Mon 3/33:00 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 1/29![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 1/29. 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 6/289:37 pmORD - BOS
Nonstop2h 32mUnited Airlines
Sat 7/57:30 pmBOS - ORD
1 stop5h 12mUnited Airlines
Deal found 1/29![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 1/29. 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.
Mon 3/101:50 pmORD - BOS
2 stops9h 30mSouthwest
Fri 3/145:40 pmBOS - ORD
1 stop4h 50mSouthwest
Deal found 1/29![Southwest logo]()
$232
This Kissandfly.com deal was found by Cheapflights users on 1/29. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/154:40 pmMDW - BOS
1 stop7h 04mMultiple Airlines
Sat 3/2210:21 pmBOS - MDW
2 stops15h 41mMultiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 1/29. 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.
Thu 2/66:00 amMDW - BOS
1 stop6h 39mDelta
Wed 2/126:05 amBOS - MDW
2 stops13h 06mDelta
Deal found 1/29![Delta logo]()
$315
Find flights from Chicago to Boston within your budget
Customize 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 2,558,603 searches. Data last updated January 30, 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 2/19
7:25 am-12:31 am
1 stop16h 06m
Boston Logan Intl
Sun 2/23
6:00 am-9:27 am
1 stop28h 27m
$146
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 3/1
4:19 pm-12:30 am
1 stop7h 11m
Boston Logan Intl
Fri 3/7
5:10 am-11:34 am
1 stop7h 24m
$146
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 2/12
7:07 am-10:41 pm
2 stops14h 34m
Boston Logan Intl
Tue 2/18
8:10 pm-11:50 am
1 stop16h 40m
$147
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 2/17
7:13 pm-1:29 pm
1 stop17h 16m
Boston Logan Intl
Fri 2/21
12:45 pm-9:15 am
1 stop21h 30m
$148
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 2/20
7:10 am-10:43 am
Nonstop2h 33m
Boston Logan Intl
Tue 2/25
8:20 pm-10:19 pm
Nonstop2h 59m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 2/26
10:05 am-1:20 pm
Nonstop2h 15m
Boston Logan Intl
Fri 2/28
7:45 pm-9:35 pm
Nonstop2h 50m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 2/28
12:50 pm-4:13 pm
Nonstop2h 23m
Boston Logan Intl
Thu 3/6
2:30 pm-4:30 pm
Nonstop3h 00m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 3/8
7:20 am-10:43 am
Nonstop2h 23m
Boston Logan Intl
Tue 3/11
1:40 pm-3:40 pm
Nonstop3h 00m
$178
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 3/1
6:00 am-11:21 am
1 stop4h 21m
Boston Logan Intl
Sat 3/8
8:55 am-10:57 am
Nonstop3h 02m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 2/24
4:00 pm-10:55 pm
1 stop5h 55m
Boston Logan Intl
Thu 2/27
5:20 pm-9:30 pm
1 stop5h 10m
$226
Showing 1-10 of 25 results
Compare providers for flights from Chicago 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 Chicago 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*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-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-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
The best insider tips for Chicago to Boston flights
Find out what our experts recommend to make the most of your Chicago to Boston trip
Airlines
![American Airlines]()
American Airlines
![United Airlines]()
United Airlines
United's Economy Plus offers extra legroom, perfect for added comfort on short domestic routes.
United's free snacks and drinks enhance the short-haul travel experience for all economy passengers.
![Delta]()
Delta
Delta offers free Wi-Fi for SkyMiles members on most domestic flights, enhancing travel productivity.
Delta Comfort Plus provides extra legroom and early boarding, ideal for a comfortable short flight.
![JetBlue]()
JetBlue
JetBlue offers free onboard Wi-Fi, ideal for staying connected during short flights.
JetBlue's Even More Space seats provide up to 38 inches of legroom, enhancing comfort.
Airports
Our travel experts
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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 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.
Travel insights for flights from Chicago to Boston
Get recent, data-driven insights about flights from Chicago to Boston including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Chicago to Boston?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Boston. Price data was last updated on January 24, 2025.
The price you pay for your flight from Chicago to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 83 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $218). Flying from Chicago to Boston in July is currently the most expensive (average of $311). 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 January 30, 2025.
It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 33% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chicago to Boston?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Boston. Price data was last updated on January 26, 2025.
Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Wednesday evenings 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 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 January 30, 2025.
The most flights from CHI to BOS are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).
Rainfall in Boston by month
Plan your trip to Boston by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.
Temperature in Boston by month
Plan your trip to Boston by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).
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 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and JetBlue from Chicago to Boston to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.1
Entertainment
7.7
Overall
8.1
Boarding
8.2
Food
7.1
Crew
8.7
Reviews
1 / 20
6.0
GoodLauren,Dec 2024
MCI - DCA
Comfort
8.1
Entertainment
7.7
Overall
8.1
Boarding
8.2
Food
7.1
Crew
8.7
Reviews
1 / 20
6.0
GoodLauren,Dec 2024
MCI - DCA
Comfort
8.1
Entertainment
7.7
Overall
8.1
Boarding
8.2
Food
7.1
Crew
8.7
Reviews
1 / 20
6.0
GoodLauren,Dec 2024
MCI - DCA
Comfort
8.1
Entertainment
7.7
Overall
8.1
Boarding
8.2
Food
7.1
Crew
8.7
Reviews
1 / 20
6.0
GoodLauren,Dec 2024
MCI - DCA
Comfort
8.1
Entertainment
7.7
Overall
8.1
Boarding
8.2
Food
7.1
Crew
8.7
Reviews
1 / 20
6.0
GoodLauren,Dec 2024
MCI - DCA
Comfort
8.1
Entertainment
7.7
Overall
8.1
Boarding
8.2
Food
7.1
Crew
8.7
Reviews
1 / 20
6.0
GoodLauren,Dec 2024
MCI - DCA
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWarwick
Sturbridge
Marlborough
Waltham
Brockton
Cambridge
Watertown
Framingham
Somerville
Chestnut Hill
Seekonk
Randolph
Lowell
West Yarmouth
Woburn
Saco
Seabrook
Salem
Brookline
Fall River
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Chicago to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chicago to Boston
Discover the top 7 airlines that operate flights from Chicago 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 30, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$38 | Average$96 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$63 | Average$316 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$69 | Average$116 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$86 | Average$240 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$256 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$153 | Average$282 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$299 | FlexibilityNo cancel fee | On-time69% |