Which airport is the most popular layover for flights between Boston and Chicago?

Philadelphia (PHL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest travel time from Boston to Chicago?

Flights connecting via Philadelphia (PHL) have the shortest average one-way travel time: 9h 52m.

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

63 flights are operational daily from Boston to Chicago as of October 2025. The most popular departure time for this route is 4:00PM, with 41% of flights per day taking off at noon.

Which layover airport offers the lowest fares from Boston to Chicago?

Flights via Tampa (TPA) offer the lowest average round-trip price of $215.

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

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

Which layover airport has the shortest connection time from Boston to Chicago?

Tampa (TPA) has the shortest average layover time for this route: 4h 44m.

What airlines fly to Chicago?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Boston according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

As of October 2025, 445 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.

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 refresh daily.

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

There are 7 operators 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?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$64 Cheap Flights from Boston to Chicago in 2025/26

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7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

10:08 am - 1:37 pmORD-BOS

2h 29mnonstop

$122JetBlue

Find Deal

Thu, Oct 23 - Sat, Oct 25

7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

7:13 pm - 10:46 pmORD-BOS

2h 33mnonstop

$124JetBlue

Find Deal

Wed, Oct 15 - Mon, Oct 20

5:40 pm - 10:05 pmBOS-MDW

5h 25m1 stop

6:05 pm - 9:20 pmMDW-BOS

2h 15mnonstop

$127Southwest

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Tue, Oct 28 - Wed, Oct 29

11:45 am - 1:40 pmBOS-ORD

2h 55mnonstop

10:25 am - 1:55 pmORD-BOS

2h 30mnonstop

$127Delta

Find Deal

Sat, Nov 1 - Sat, Nov 8

6:45 am - 8:52 amBOS-ORD

3h 07mnonstop

1:04 pm - 4:32 pmORD-BOS

2h 28mnonstop

$128American Airlines

Find Deal

Thu, Nov 20 - Thu, Nov 27

11:55 am - 7:10 pmBOS-MDW

8h 15m2 stops

5:35 pm - 8:50 pmMDW-BOS

2h 15mnonstop

$132Southwest

Find Deal

Tue, Oct 28 - Sat, Nov 1

9:53 am - 11:43 amBOS-ORD

2h 50mnonstop

6:15 am - 9:30 amORD-BOS

2h 15mnonstop

$133United Airlines

Find Deal

Tue, Oct 21 - Sun, Oct 26

4:25 pm - 6:20 pmBOS-ORD

2h 55mnonstop

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

$136United Airlines

Find Deal

Wed, Oct 15 - Sat, Oct 18

7:20 am - 9:22 amBOS-ORD

3h 02mnonstop

3:50 pm - 7:23 pmORD-BOS

2h 33mnonstop

$137Delta

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Thu, Oct 23 - Sat, Oct 25

6:57 am - 8:55 amBOS-ORD

2h 58mnonstop

6:05 am - 9:32 amORD-BOS

2h 27mnonstop

$156American Airlines

Find Deal

Thu, Oct 23 - Sun, Oct 26

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

JetBlue

Oct 23

BOS7:09 amBoston Logan Intl

3h 13m

ORD9:22 amChicago O'Hare Intl

Oct 25

ORD10:08 amChicago O'Hare Intl

2h 29m

BOS1:37 pmBoston Logan Intl

$122

Find similar

JetBlue

Oct 15

BOS7:09 amBoston Logan Intl

3h 13m

ORD9:22 amChicago O'Hare Intl

Oct 20

ORD7:13 pmChicago O'Hare Intl

2h 33m

BOS10:46 pmBoston Logan Intl

$124

Find similar

JetBlue

Nov 1

BOS7:00 amBoston Logan Intl

3h 05m

ORD9:05 amChicago O'Hare Intl

Nov 5

ORD6:55 pmChicago O'Hare Intl

2h 32m

BOS10:27 pmBoston Logan Intl

$129

Find similar

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets

Delta

Nov 1

BOS11:45 amBoston Logan Intl

2h 55m

ORD1:40 pmChicago O'Hare Intl

Nov 8

ORD10:25 amChicago O'Hare Intl

2h 30m

BOS1:55 pmBoston Logan Intl

$127

Find similar

Delta

Oct 23

BOS7:20 amBoston Logan Intl

3h 02m

ORD9:22 amChicago O'Hare Intl

Oct 25

ORD3:50 pmChicago O'Hare Intl

2h 33m

BOS7:23 pmBoston Logan Intl

$137

Find similar

Delta

Oct 23

BOS7:20 amBoston Logan Intl

3h 02m

ORD9:22 amChicago O'Hare Intl

Oct 26

ORD7:05 amChicago O'Hare Intl

2h 24m

BOS10:29 amBoston Logan Intl

$157

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Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Sat 10/25

10:08 am-1:37 pm

Nonstop2h 29m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Mon 10/20

7:13 pm-10:46 pm

Nonstop2h 33m

$124

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/28

5:40 pm-10:05 pm

1 stop5h 25m

Chicago Midway

Wed 10/29

6:05 pm-9:20 pm

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/1

11:45 am-1:40 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 11/8

10:25 am-1:55 pm

Nonstop2h 30m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/20

6:45 am-8:52 am

Nonstop3h 07m

Chicago O'Hare Intl

Thu 11/27

1:04 pm-4:32 pm

Nonstop2h 28m

$128

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/28

11:55 am-7:10 pm

2 stops8h 15m

Chicago Midway

Sat 11/1

5:35 pm-8:50 pm

Nonstop2h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/21

9:53 am-11:43 am

Nonstop2h 50m

Chicago O'Hare Intl

Sun 10/26

6:15 am-9:30 am

Nonstop2h 15m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

4:25 pm-6:20 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 10/18

6:30 am-9:56 am

Nonstop2h 26m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

7:20 am-9:22 am

Nonstop3h 02m

Chicago O'Hare Intl

Sat 10/25

3:50 pm-7:23 pm

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

6:57 am-8:55 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 10/26

6:05 am-9:32 am

Nonstop2h 27m

$156

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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

Layovers

Other information

What is the typical price of a round-trip flight between Boston and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $197.

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 Friday when prices can be found for as low as $321. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Chicago for around $434.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $273. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

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 $251 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as $225 on momondo.

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

There are 4 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.

How have Boston to Chicago flight prices changed over time?

As of October 2025, prices for Boston to Chicago flights are approximately 21% 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 round-trip 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

Best Price Found	$128
Fastest flight time	2h 40m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Boston in the past 72 hours is $128. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $206.

The fastest flight from Boston to Chicago takes 2h 40m

Direct flights go from Boston to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Boston Logan Intl to Chicago by plane?
A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 40m 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 refresh daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?
There are 7 operators 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?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Boston to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Boston to Chicago is Boeing 737-800 (26.61% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (12.40%), Boeing 737-900 (11.77%), and Airbus A220-300 (10.23%).
What is the most popular airline from Boston to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Boston to Chicago is American Airlines (29% of total bookings). The next most popular airlines are United Airlines (26%), Southwest (17%), and Delta (15%).

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
Spirit Airlines	PriceFrom $67	Free Cancellation	Rating 6.3 8,080 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $83	Free Cancellation	Rating 7.2 2,908 reviews	Search JetBlue flights
United Airlines	PriceFrom $97	Free Cancellation	Rating 7.4 8,957 reviews	Search United Airlines flights
Frontier	PriceFrom $100	Free Cancellation	Rating 5.8 3,144 reviews	Search Frontier flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 7,969 reviews	Search Delta flights
Southwest	PriceFrom $118	Free Cancellation	Rating 8.0 4,234 reviews	Search Southwest flights
American Airlines	PriceFrom $137	Free Cancellation	Rating 7.2 11,041 reviews	Search American Airlines flights

Southwest Flights From Boston to Chicago
The lowest priced Southwest flight from Boston to Chicago from the last 72 hours was $118. Generally, Southwest has 23 flights on this route every week with an average price of $238. Southwest is rated 8.0/10 by our users.
Delta Flights From Boston to Chicago
Delta is also a popular choice for this route. Delta flight deals for Boston to Chicago start from as low as $114 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $299. Delta operates 9 flights to Chicago from Boston in an average week. Users have rated it 7.9/10 across 7,969 reviews.

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Saint John

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?

momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Chicago from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

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

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Cheap flights from Boston to Chicago from $64

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 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

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Our best Delta deals on Boston to Chicago flight tickets

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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 typical price of a round-trip flight between Boston and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $197.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $273. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

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 4 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.

How have Boston to Chicago flight prices changed over time?

As of October 2025, prices for Boston to Chicago flights are approximately 21% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Boston and Chicago?

Philadelphia (PHL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Boston to Chicago?

Flights via Tampa (TPA) offer the lowest average round-trip price of $215.

Which layover airport has the shortest travel time from Boston to Chicago?

Flights connecting via Philadelphia (PHL) have the shortest average one-way travel time: 9h 52m.

Which layover airport has the shortest connection time from Boston to Chicago?

Tampa (TPA) has the shortest average layover time for this route: 4h 44m.

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

63 flights are operational daily from Boston to Chicago as of October 2025. The most popular departure time for this route is 4:00PM, with 41% of flights per day taking off at noon.

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

As of October 2025, 445 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off 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

Best Price Found

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?

What is the most popular airline 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

Southwest Flights From Boston to Chicago

Delta Flights From Boston to Chicago

Traveling to a place near 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, organize 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.