Cheap flights from Boston (BOS) to Chicago (CHI) from $39

This is the cheapest one-way flight price, found on 9/27. Prices may vary by date and flight preferences.
BOS — CHI
Oct 3 — Oct 101

The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 0 days in advance, depart on a Saturday or Wednesday and return on a Saturday

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

All the information you need to plan the best BOS to CHI flight in 2023: compare Boston to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

June

Cheapest in

January

Round-trip from

$207

One-way from

$54
High demand for flights, 23% potential price rise
Best time to find cheap flights, 37% potential price drop
From Boston Logan Intl to Chicago (CHI)
One-way flight from Boston Logan Intl to Chicago (CHI)

BOS - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

What is the cheapest day to fly round-trip from Boston to Chicago?

Travelers have found that booking a Friday departure is the best way to save up to 32% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

What is the cheapest month to fly from Boston 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 Boston in January are about $251 on average during January, but can be found for as low as $118.

When is the cheapest time to fly from Boston to Chicago (BOS - CHI)?

Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Boston to Chicago by exploring options for tickets in the evening.

Cheap American Airlines flights from Boston to Chicago

Consider these cheap American Airlines flights we've found departing from Boston to Chicago. It's recommended that users confirm their flight details before booking.
  • If you’re traveling from Boston to Chicago, one of the more common airlines traveling that route is American Airlines. Flights from American Airlines traveling this route typically cost $299.40 RT. This price is typically 30% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $49. The most popular departure airport in Boston when flying to Chicago is Boston Logan Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, American Airlines flights are 10% more popular than any other airline flying that same route.

Cheap JetBlue flights from Boston to Chicago

Have a look at some of the cheapest available JetBlue flights departing from Boston and landing in Chicago. Check back soon if you're not seeing flights that suit your needs.
  • JetBlue is one of the most popular airlines used for those traveling from Boston to Chicago. Flights from JetBlue traveling this route typically cost $325.83 RT. This price is typically 27% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $94. The most popular departure airport in Boston when flying to Chicago is Boston Logan Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, JetBlue flights are 8% more popular than any other airline flying that same route.

Cheap Boston to Chicago flights in September & October 2023

The best prices found for BOS to CHI flights for September, October
The lowest fares we've come across on flights traveling from Boston to Chicago in September and October 2023. Check back in a little while for more flight options.

Boston to Chicago 2023 flight deals

Cheap flights to Chicago from Boston found for this year
The lowest fares we've come across on flights traveling from Boston to Chicago in September and October 2023. Check back in a little while for more flight options.

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
For a quicker trip, book one of these direct flights from Boston to Chicago. Search for alternative flights from Boston to Chicago by utilizing the search form above.

Boston to Chicago flights leaving soon

Late deals on return flights to Chicago from Boston, departing today and this week
Check out these flights departing soon from Boston to Chicago. Users should examine the flight details to ensure there are no surprises.

One-way flights to Chicago from Boston

The cheapest one-way flights from Boston to Chicago
If you're seeking multiple options on one-way flights from Boston to Chicago, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Boston to Chicago should utilize the search form at the the top of the page.

Find flights from Boston to Chicago within your budget

Use the slider to find flights from Boston to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$78 - $156

Route

Depart

Return

Price

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/24

1 stop5h 05m

Chicago Midway

Wed 10/25

1 stop10h 26m

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/24

1 stop5h 05m

Chicago Midway

Sat 10/28

1 stop14h 33m

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/4

Nonstop3h 00m

Chicago O'Hare Intl

Wed 11/8

Nonstop2h 17m

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/11

Nonstop2h 48m

Chicago O'Hare Intl

Tue 11/14

Nonstop2h 13m

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 11/7

1 stop6h 43m

Chicago O'Hare Intl

Tue 11/7

Nonstop2h 17m

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/31

1 stop8h 59m

Chicago Midway

Sat 11/4

1 stop11h 16m

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/4

Nonstop2h 57m

Chicago O'Hare Intl

Sat 11/4

Nonstop2h 21m

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/18

1 stop16h 34m

Chicago O'Hare Intl

Tue 10/24

1 stop11h 09m

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/2

Nonstop2h 49m

Chicago O'Hare Intl

Wed 11/8

Nonstop2h 25m

Flights are sorted by cheapest first

Deals found on 9/26

Reviews of airlines servicing Chicago

See what other customers who have flown with American Airlines, JetBlue and United Airlines 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.
Delta
7.9
Good
3,023 reviews

Food

7.2

Comfort

7.9

Boarding

8.0

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 10

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

Delta
7.9
Good
3,023 reviews
Delta
7.9
Good
3,023 reviews

Food

7.2

Comfort

7.9

Boarding

8.0

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 10

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

Porter Airlines
7.6
Good
27 reviews
Delta
7.9
Good
3,023 reviews

Food

7.2

Comfort

7.9

Boarding

8.0

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 10

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

Allegiant Air
7.5
Good
103 reviews
Delta
7.9
Good
3,023 reviews

Food

7.2

Comfort

7.9

Boarding

8.0

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 10

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

Sun Country Air
7.4
Good
94 reviews
Delta
7.9
Good
3,023 reviews

Food

7.2

Comfort

7.9

Boarding

8.0

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 10

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

United Airlines
7.4
Good
1,890 reviews
Delta
7.9
Good
3,023 reviews

Food

7.2

Comfort

7.9

Boarding

8.0

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 10

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

Related info for your journey

Useful info, stats and facts about Boston to Chicago flights.

What airport do you fly from for flights from Boston to Chicago?

Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Chicago from Boston. Booking flights from Logan Intl (BOS) to Chicago should be relatively easy as there are 51 daily outbound flights to Chicago from 7 different airlines.

Can I find flights from Boston to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Boston to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $78, but on average you can expect to pay $99.

Are there nonstop flights from Boston to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Boston to Chicago under $100. A good price for a nonstop flight from Boston to Chicago is less than $126.

Are there last-minute flights available from Boston to Chicago for under $200?

There are currently 20+ open flights from Boston to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Boston to Chicago?

You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from Boston to Chicago on average per day?

82 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 7% of flight departures
Morning (6am - Noon) - 33% of flight departures
Afternoon (Noon - 6pm) - 51% of flight departures
Evening (6pm - Midnight) - 9% of flight departures

How long is the flight from Boston to Chicago?

For as low as $78, Frontier can have you in Chicago from Boston in 2h 48m. Airlines will cover a distance of 869 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from Boston to Chicago round-trip?

Our cheapest airline available from Boston to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $78 on this airline. Additional options worth looking into are JetBlue and American Airlines, starting at $88 and $90 round-trip. You may be able to fly from Boston to Chicago for 68% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Boston to Chicago one-way?

To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $39. JetBlue flights start at $44 while deals on Spirit Airlines start at $51 one-way.

What are the most popular routes from Boston to Chicago?

What are the most popular airlines that fly from Boston to Chicago?

What are the most reliable airlines from Boston to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Chicago on time: Japan Airlines (90%), ANA (88%), SkyWest Airlines (82%).

What are the cheapest flights from Boston to Chicago?

The cheapest flight price from Boston to Chicago is $79. On average you can expect to pay $600. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $88.

What does BOS to ORD mean?

BOS and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. BOS to ORD refers to a flight route from Boston Logan Intl Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

Top 6 airlines flying from Boston to Chicago

The chart below displays the airlines Cheapflights users traveling from Boston to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$49Average$299FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
JetBlueCheapest$79Average$278FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
United AirlinesCheapest$82Average$276FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$94Average$326FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$109Average$267FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Spirit AirlinesCheapest$141Average$233FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights

Hourly flight availability from Boston to Chicago

See what time of day planes typically take off from Boston to Chicago
20%of flight departuresEarly morningMidnight to 6 am
34%of flight departuresMorning6 am to noon
43%of flight departuresAfternoonNoon to 6 pm
3%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Boston to Chicago

See how many times per day planes take to the skies headed from Boston to Chicago
Sunday51daily flights
Monday66daily flights
Tuesday46daily flights
Wednesday52daily flights
Thursday56daily flights
Friday61daily flights
Saturday31daily flights

Fly with Cheapflights

What makes Cheapflights the go-to destination for all your flight needs

How does Cheapflights help users find flights from Boston to Chicago?

Cheapflights makes it easy to find Boston to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Boston to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Boston to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Boston to Chicago with no change fees?

Yes, we can. To see specific flights from Boston to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Boston to Chicago become cheaper?

Yes! Start tracking prices for Boston to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, navigate to the search form above to perform a search, which will then prompt you for a valid email address to use the tool.

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