What is the cheapest airline that flies from Boston Logan Intl to Chicago?

Southwest, United Airlines, and Delta are the most popular carriers operating from Boston Logan Intl to Chicago

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

The number of flights available between Boston and Chicago is 422 per week as of October 2025. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

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

60 flights are operational daily from Boston to Chicago as of October 2025. The most popular departure time for this route is 16:00, with 43% of flights per day taking off in the afternoon.

When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?

Prices for flights from Boston Logan Intl Airport to Chicago were last updated today.

How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?

There is 1 operator available for flights from Boston Logan Intl Airport to Chicago as of October 2025.

How old do you have to be to fly from Boston Logan Intl Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

£43 Cheap Flights from Boston to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Voted winner of Europe's Best Travel App 2023

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Boston to Chicago

Round-trip

One-way

Last minute

Direct

Cheap return flights

Enter your travel dates to find the best prices.

06:00 - 08:04BOS-ORD

3h 04mdirect

09:13 - 12:46ORD-BOS

2h 33mdirect

£89United Airlines

Find Deal

Fri, 16 Jan - Sun, 18 Jan

05:10 - 12:15BOS-ORD

8h 05m1 stop

13:45 - 22:55ORD-BOS

8h 10m1 stop

£93Southwest

Find Deal

Sat, 31 Jan - Thu, 5 Feb

12:50 - 14:47BOS-ORD

2h 57mdirect

05:30 - 12:30ORD-BOS

6h 00m1 stop

£95Delta

Find Deal

Thu, 4 Dec - Thu, 11 Dec

13:40 - 18:43BOS-ORD

6h 03m1 stop

15:50 - 19:14ORD-BOS

2h 24mdirect

£98Delta

Find Deal

Fri, 5 Dec - Fri, 12 Dec

07:45 - 09:45BOS-ORD

3h 00mdirect

13:55 - 17:15ORD-BOS

2h 20mdirect

£99United Airlines

Find Deal

Thu, 6 Nov - Sat, 8 Nov

07:45 - 09:45BOS-ORD

3h 00mdirect

06:15 - 09:30ORD-BOS

2h 15mdirect

£100United Airlines

Find Deal

Thu, 6 Nov - Sun, 9 Nov

06:00 - 08:00BOS-ORD

3h 00mdirect

18:21 - 21:49ORD-BOS

2h 28mdirect

£101United Airlines

Find Deal

Fri, 31 Oct - Sat, 1 Nov

12:02 - 17:09BOS-ORD

6h 07m1 stop

18:17 - 21:45ORD-BOS

2h 28mdirect

£101United Airlines

Find Deal

Tue, 9 Dec - Sat, 13 Dec

08:30 - 10:35BOS-ORD

3h 05mdirect

10:45 - 14:09ORD-BOS

2h 24mdirect

£106JetBlue

Find Deal

Wed, 17 Dec - Sat, 17 Jan

15:55 - 17:55BOS-ORD

3h 00mdirect

18:55 - 22:27ORD-BOS

2h 32mdirect

£114JetBlue

Find Deal

Tue, 4 Nov - Mon, 10 Nov

United Airlines flights from Boston to Chicago

Our best United Airlines deals on Boston to Chicago flight tickets

United Airlines

16 Jan

BOS06:00Boston Logan Intl

3h 04m

ORD08:04Chicago O'Hare Intl

18 Jan

ORD09:13Chicago O'Hare Intl

2h 33m

BOS12:46Boston Logan Intl

£89

Find similar

United Airlines

6 Nov

BOS07:45Boston Logan Intl

3h 00m

ORD09:45Chicago O'Hare Intl

8 Nov

ORD13:55Chicago O'Hare Intl

2h 20m

BOS17:15Boston Logan Intl

£99

Find similar

United Airlines

6 Nov

BOS07:45Boston Logan Intl

3h 00m

ORD09:45Chicago O'Hare Intl

9 Nov

ORD06:15Chicago O'Hare Intl

2h 15m

BOS09:30Boston Logan Intl

£100

Find similar

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets

Delta

4 Dec

BOS12:50Boston Logan Intl

2h 57m

ORD14:47Chicago O'Hare Intl

11 Dec

ORD05:30Chicago O'Hare Intl

6h 00m

1 stop

BOS12:30Boston Logan Intl

£95

Find similar

Delta

5 Dec

BOS13:40Boston Logan Intl

6h 03m

1 stop

ORD18:43Chicago O'Hare Intl

12 Dec

ORD15:50Chicago O'Hare Intl

2h 24m

BOS19:14Boston Logan Intl

£98

Find similar

Delta

8 Nov

BOS16:10Boston Logan Intl

2h 57m

ORD18:07Chicago O'Hare Intl

9 Nov

ORD07:10Chicago O'Hare Intl

2h 26m

BOS10:36Boston Logan Intl

£102

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 16/1

06:00-08:04

Nonstop3h 04m

Chicago O'Hare Intl

Sun 18/1

09:13-12:46

Nonstop2h 33m

£89

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 31/1

05:10-12:15

1 stop8h 05m

Chicago O'Hare Intl

Thu 5/2

13:45-22:55

1 stop8h 10m

£93

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/12

12:50-14:47

Nonstop2h 57m

Chicago O'Hare Intl

Thu 11/12

05:30-12:30

1 stop6h 00m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/12

13:40-18:43

1 stop6h 03m

Chicago O'Hare Intl

Fri 12/12

15:50-19:14

Nonstop2h 24m

£98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/11

07:45-09:45

Nonstop3h 00m

Chicago O'Hare Intl

Sat 8/11

13:55-17:15

Nonstop2h 20m

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/11

07:45-09:45

Nonstop3h 00m

Chicago O'Hare Intl

Sun 9/11

06:15-09:30

Nonstop2h 15m

£100

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 31/10

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sat 1/11

18:21-21:49

Nonstop2h 28m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/12

12:02-17:09

1 stop6h 07m

Chicago O'Hare Intl

Sat 13/12

18:17-21:45

Nonstop2h 28m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 17/12

08:30-10:35

Nonstop3h 05m

Chicago O'Hare Intl

Sat 17/1

10:45-14:09

Nonstop2h 24m

£106

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/11

15:55-17:55

Nonstop3h 00m

Chicago O'Hare Intl

Mon 10/11

18:55-22:27

Nonstop2h 32m

£114

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Boston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Boston is in September. Flight prices, which tend to average around £139, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Boston during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £147.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as £162. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around £634.

What is the cheapest time of day to depart on your flight to Chicago?

Flying to Chicago from Boston in the morning is the least expensive time of day to depart. momondo users have found prices as low as £221 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £378.

What is the cheapest Boston Logan Intl to Chicago flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £186 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as £168 on momondo.

What cabin class options are available on Boston Logan Intl to Chicago flights?

There are 3 cabin classes available to choose from on Boston Logan Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Boston to Chicago flights?

No. A direct flight is the cheapest option for a flight between Boston to Chicago.

How have Boston to Chicago flight prices changed over time?

As of October 2025, prices for Boston to Chicago flights are approximately 20% cheaper when compared to flights at the same time last year.

When to book flights from Boston to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated return price

Cheap Boston to Chicago (BOS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago

Fastest flight time	2h 49m
Direct flights	Every day
Airports in Chicago	1 airport

The fastest flight from Boston to Chicago takes 2h 49m

Direct flights go from Boston to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Boston Logan Intl to Chicago by plane?
Chicago is 847.9 mi away from Boston Logan Intl. 2h 49m is a normal flight duration for this route.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?
Prices for flights from Boston Logan Intl Airport to Chicago were last updated today.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?
There is 1 operator available for flights from Boston Logan Intl Airport to Chicago as of October 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Boston to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Boston to Chicago is Boeing 737-800, representing 26.24% of all bookings. The subsequent popular models are Boeing 737-900 at 12.09%, Boeing 737 MAX 8 at 11.69%, and Airbus A220-300 at 9.90%.

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom £73	Free Cancellation	Rating 7.2 11,024 reviews		Search American Airlines flights

American Airlines Flights From Boston to Chicago
American Airlines operates around 42 flights from Boston to Chicago every week. The average price of these flights found in the last 72 hours has been £155, but momondo users have found American Airlines deals from Boston to Chicago from as low as £98 round-trip. American Airlines has been scored 7.2/10 in 11,024 reviews.

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Chicago?

It is quick and easy to find Boston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Boston to Chicago with flexible booking policies on momondo?

Flights from Boston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Boston to Chicago?

momondo helps you find the best flight between Boston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Boston and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Thu 20/11

Thu 27/11

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular Cities in the United States

Flights to New Yorkfrom £253

Flights to Orlandofrom £241

Flights to Los Angelesfrom £355

Flights to Miamifrom £346

Flights to San Franciscofrom £362

Flights to Bostonfrom £326

Flights to Las Vegasfrom £430

Flights to Washington, D.C.from £326

Flights to Atlantafrom £393

Flights to Dallasfrom £355

Flights to Houstonfrom £377

Flights to Tampafrom £426

Cheap flights from Boston to Chicago from £47

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 15/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Boston to Chicago

Cheap return flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

United Airlines flights from Boston to Chicago

Our best United Airlines deals on Boston to Chicago flight tickets

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Boston to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Boston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as £162. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around £634.

What is the cheapest time of day to depart on your flight to Chicago?

Flying to Chicago from Boston in the morning is the least expensive time of day to depart. momondo users have found prices as low as £221 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £378.

What is the cheapest Boston Logan Intl to Chicago flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Boston Logan Intl to Chicago flights?

There are 3 cabin classes available to choose from on Boston Logan Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Boston to Chicago flights?

No. A direct flight is the cheapest option for a flight between Boston to Chicago.

How have Boston to Chicago flight prices changed over time?

As of October 2025, prices for Boston to Chicago flights are approximately 20% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Boston Logan Intl to Chicago?

Southwest, United Airlines, and Delta are the most popular carriers operating from Boston Logan Intl to Chicago

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

60 flights are operational daily from Boston to Chicago as of October 2025. The most popular departure time for this route is 16:00, with 43% of flights per day taking off in the afternoon.

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

The number of flights available between Boston and Chicago is 422 per week as of October 2025. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

When to book flights from Boston to Chicago

Cheap Boston to Chicago (BOS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago

Fastest flight time

Direct flights

Airports in Chicago

How far is Boston Logan Intl to Chicago by plane?

When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?

How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?

How old do you have to be to fly from Boston Logan Intl Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Boston to Chicago?

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo

American Airlines Flights From Boston to Chicago

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Chicago?

Can I find flights from Boston to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Boston to Chicago?

I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago