American Airlines offers Main Cabin Extra seats with more legroom for added comfort.
Flagship Business class includes priority boarding and lounge access for a seamless experience.
$79+ Cheap flights from Boston (BOS) to Chicago (CHI)
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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
ene. 28 — feb. 41
1 adult, Economy
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Find cheap flights from Boston to Chicago 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 Boston Logan Intl to Chicago are usually found in September or January, booked 76 days in advance, depart on a Wednesday or Friday and return on a Wednesday
Cheap flight deals from Boston to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). 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 enero 23, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $147 (FlightHub) |
One-way from | $79 (Southwest) |
Popular in | April |
Cheapest in | September |
Average price | $197 |
Good round-trip deal | $224 or less |
Good one-way deal | $133 or less |
Find flight deals from Boston to Chicago
Cheapest flights from Boston to ChicagoExplore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 23, 2025.
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 23, 2025.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/206:00 amBOS - MDW
1 stop14h 29mFrontier
jue. 2/274:04 pmMDW - BOS
1 stop17h 17mFrontier
Deal found 1/23![Frontier logo]()
$147
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/44:47 pmBOS - ORD
1 stop8h 11mMultiple Airlines
vie. 3/710:00 amORD - BOS
1 stop13h 44mMultiple Airlines
Deal found 1/23![Multiple Airlines logo]()
$147
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.
lun. 3/105:10 amBOS - ORD
1 stop12h 21mFrontier
jue. 3/134:30 pmORD - BOS
1 stop18h 24mFrontier
Deal found 1/23![Frontier logo]()
$148
This Mytrip deal was found by Cheapflights users on 1/22. 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.
sáb. 2/86:25 amBOS - ORD
1 stop10h 45mSpirit Airlines
mié. 2/125:15 amORD - BOS
2 stops14h 49mSpirit Airlines
Deal found 1/22![Spirit Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 1/22. 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.
jue. 2/136:50 amBOS - MDW
Nonstop2h 55mSouthwest
dom. 2/168:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/22![Southwest logo]()
$157
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/249:20 amBOS - ORD
Nonstop3h 02mUnited Airlines
mar. 2/257:30 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 1/23![United Airlines logo]()
$157
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.
lun. 2/2412:40 pmBOS - ORD
1 stop5h 05mJetBlue
jue. 2/2712:50 pmORD - BOS
Nonstop2h 23mJetBlue
Deal found 1/23![JetBlue logo]()
$167
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/136:34 amBOS - ORD
Nonstop3h 05mAmerican Airlines
dom. 2/168:05 amORD - BOS
Nonstop2h 14mAmerican Airlines
Deal found 1/23![American Airlines logo]()
$188
This Delta deal was found by Cheapflights users on 1/22. 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.
sáb. 4/265:40 pmBOS - ORD
Nonstop3h 04mDelta
mié. 4/3010:10 amORD - BOS
Nonstop2h 28mDelta
Deal found 1/22![Delta logo]()
$198
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/132:45 pmBOS - ORD
1 stop7h 45mSouthwest
dom. 2/1611:25 amORD - BOS
1 stop4h 10mSouthwest
Deal found 1/23![Southwest logo]()
$227
This Mytrip deal was found by Cheapflights users on 1/22. 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.
mar. 2/185:07 pmBOS - RFD
1 stop16h 06mMultiple Airlines
mié. 2/196:36 pmRFD - BOS
1 stop13h 32mMultiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$279
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.
jue. 2/135:20 amBOS - MDW
1 stop8h 45mDelta
dom. 2/169:33 amMDW - BOS
1 stop5h 20mDelta
Deal found 1/23![Delta logo]()
$302
Find flights from Boston to Chicago within your budget
Customize your flight search to find flights from Boston 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 2,558,603 searches. Data last updated enero 23, 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
jue. 2/20
6:00 am-7:29 pm
1 stop14h 29m
Chicago Midway
jue. 2/27
4:04 pm-10:21 am
1 stop17h 17m
$147
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mié. 2/5
6:00 am-12:45 pm
1 stop7h 45m
Chicago O'Hare Intl
dom. 2/16
7:10 am-3:42 pm
1 stop7h 32m
$147
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
lun. 3/10
5:10 am-4:31 pm
1 stop12h 21m
Chicago O'Hare Intl
jue. 3/13
4:30 pm-11:54 am
1 stop18h 24m
$148
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mié. 2/5
6:25 am-4:10 pm
1 stop10h 45m
Chicago O'Hare Intl
mié. 2/12
5:15 am-9:04 pm
2 stops14h 49m
$152
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
jue. 2/13
6:50 am-8:45 am
Nonstop2h 55m
Chicago Midway
dom. 2/16
8:05 am-11:20 am
Nonstop2h 15m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
lun. 2/24
10:00 am-12:00 pm
Nonstop3h 00m
Chicago O'Hare Intl
vie. 2/28
12:50 pm-4:13 pm
Nonstop2h 23m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
lun. 2/24
8:20 pm-10:19 pm
Nonstop2h 59m
Chicago O'Hare Intl
lun. 3/3
7:10 am-10:43 am
Nonstop2h 33m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
vie. 3/21
5:30 am-9:38 am
1 stop5h 08m
Chicago O'Hare Intl
mié. 3/26
4:05 pm-7:25 pm
Nonstop2h 20m
$183
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
jue. 2/13
5:20 am-7:21 am
Nonstop3h 01m
Chicago O'Hare Intl
dom. 2/16
7:00 am-10:20 am
Nonstop2h 20m
$188
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
jue. 2/13
5:45 am-2:00 pm
1 stop9h 15m
Chicago O'Hare Intl
mar. 2/18
11:25 am-8:30 pm
1 stop8h 05m
$227
Showing 1-10 of 28 results
Compare providers for flights from Boston to Chicago
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 Boston to Chicago 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 Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Boston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Chicago 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 Boston-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
The best insider tips for Boston to Chicago flights
Find out what our experts recommend to make the most of your Boston to Chicago trip
Airlines
![American Airlines]()
American Airlines
![United Airlines]()
United Airlines
United Economy Plus offers extra legroom seats for a more comfortable journey.
United's Polaris Business Class features lie-flat seats and upscale amenities.
![Delta]()
Delta
Delta offers free Wi-Fi for SkyMiles members, enhancing productivity during flights.
Delta Comfort Plus provides extra legroom and earlier boarding for added convenience.
![JetBlue]()
JetBlue
JetBlue offers free onboard Wi-Fi and seatback screens for entertainment.
Even More Space seats provide up to 38 inches of legroom for added comfort.
![Spirit Airlines]()
Spirit Airlines
Spirit's Big Front Seats offer 11 inches more legroom for a comfortable ride.
Spirit's self-service bag drop saves time at the airport.
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 Boston to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston 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 Boston to Chicago
Get recent, data-driven insights about flights from Boston to Chicago including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Boston to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Boston to Chicago. Price data was last updated on January 17, 2025.
The best time to book flights from Boston to Chicago is 49 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Boston to Chicago?
Currently, August is the cheapest month in which you can book a flight from Boston to Chicago (average of $245). Flying from Boston to Chicago in March is currently the most expensive (average of $322). 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 BOS to CHI?
Find hourly flight availability from Boston 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 enero 23, 2025.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 30% on flights from Boston to Chicago by exploring options for tickets in the evening.
What is the cheapest day to fly from Boston to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Boston to Chicago. Price data was last updated on January 21, 2025.
Travelers seeking maximum savings on their Boston to Chicago 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.
Weekly flight availability from Boston to Chicago
Explore weekly flight availability from Boston to Chicago. 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 enero 23, 2025.
The most flights from BOS to CHI are scheduled on a Thursday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, 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 23.0 F).
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 enero 23, 2025.
See what other customers who have flown with JetBlue, Delta and Frontier from Boston to Chicago have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
4,647 reviews
Food
7.2
Boarding
8.2
Crew
8.7
Entertainment
7.7
Comfort
8.1
Overall
8.1
Reviews
1 / 10
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
4,647 reviews
4,647 reviews
Food
7.2
Boarding
8.2
Crew
8.7
Entertainment
7.7
Comfort
8.1
Overall
8.1
Reviews
1 / 10
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
9,699 reviews
4,647 reviews
Food
7.2
Boarding
8.2
Crew
8.7
Entertainment
7.7
Comfort
8.1
Overall
8.1
Reviews
1 / 10
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
8,508 reviews
4,647 reviews
Food
7.2
Boarding
8.2
Crew
8.7
Entertainment
7.7
Comfort
8.1
Overall
8.1
Reviews
1 / 10
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
3,185 reviews
4,647 reviews
Food
7.2
Boarding
8.2
Crew
8.7
Entertainment
7.7
Comfort
8.1
Overall
8.1
Reviews
1 / 10
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
8,970 reviews
4,647 reviews
Food
7.2
Boarding
8.2
Crew
8.7
Entertainment
7.7
Comfort
8.1
Overall
8.1
Reviews
1 / 10
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Related info for your journey
Find useful and relevant information for your journey from Boston to Chicago. 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 locationsMerrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Boston to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Boston to Chicago
Discover the top 7 airlines that operate flights from Boston 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 2,558,603 searches. Data last updated enero 23, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$106 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$81 | Average$239 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$344 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$144 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$266 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$147 | Average$312 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$149 | Average$239 | FlexibilityNo cancel fee | On-time63% |