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

JetBlue, Frontier, and Southwest are the most popular carriers operating from Boston Logan Intl to Illinois

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

As of October 2025, 159 flights take off from Boston and land in Illinois each week. The most common flight departure day for this route is Thu, with 50% of weekly flights taking off on this day.

What airlines fly to Illinois?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Illinois from Boston according to our data. American Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 7 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

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

22 flights are operational daily from Boston to Illinois as of October 2025. The most popular departure time for this route is 4:00PM, with 47% of flights per day taking off in the afternoon.

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

Prices for flights from Boston Logan Intl Airport to Illinois are refreshed on a daily basis.

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

The number of operators available for flights from Boston Logan Intl Airport to Illinois is 7 as of October 2025.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Boston Logan Intl Airport to Illinois.

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

The necessary travel and health documents for your Illinois 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.

$60 Cheap Flights from Boston to Illinois in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:05 pm - 6:02 pmBOS-ORD

2h 57mnonstop

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

$118Delta

Find Deal

jue., dic. 4 - dom., dic. 7

4:05 pm - 6:02 pmBOS-ORD

2h 57mnonstop

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

$119Delta

Find Deal

jue., dic. 4 - dom., dic. 7

10:40 am - 12:40 pmBOS-ORD

3h 00mnonstop

7:30 am - 10:49 amORD-BOS

2h 19mnonstop

$122United Airlines

Find Deal

lun., nov. 17 - jue., feb. 19

5:15 am - 7:00 amBOS-MDW

2h 45mnonstop

9:35 am - 12:50 pmMDW-BOS

2h 15mnonstop

$127Southwest

Find Deal

dom., nov. 9 - lun., nov. 10

7:10 am - 9:15 amBOS-ORD

3h 05mnonstop

6:55 pm - 10:27 pmORD-BOS

2h 32mnonstop

$127JetBlue

Find Deal

sáb., nov. 15 - lun., nov. 17

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

10:00 am - 1:20 pmORD-BOS

2h 20mnonstop

$130JetBlue

Find Deal

jue., nov. 13 - sáb., nov. 15

4:15 pm - 6:19 pmBOS-ORD

3h 04mnonstop

6:11 pm - 9:44 pmORD-BOS

2h 33mnonstop

$131United Airlines

Find Deal

mié., dic. 24 - mié., dic. 31

7:00 am - 9:05 amBOS-ORD

3h 05mnonstop

1:25 pm - 4:43 pmORD-BOS

2h 18mnonstop

$137American Airlines

Find Deal

vie., ene. 16 - lun., ene. 19

5:15 am - 7:00 amBOS-MDW

2h 45mnonstop

5:15 pm - 10:55 pmMDW-BOS

4h 40m1 stop

$137Southwest

Find Deal

dom., nov. 9 - lun., nov. 10

5:22 pm - 7:36 pmBOS-ORD

3h 14mnonstop

7:00 am - 10:25 amORD-BOS

2h 25mnonstop

$146American Airlines

Find Deal

lun., nov. 10 - mar., nov. 11

United Airlines flights from Boston to Illinois

Our best United Airlines deals on Boston to Illinois flight tickets

United Airlines

Nov 17

BOS10:40 amBoston Logan Intl

3h 00m

ORD12:40 pmChicago O'Hare Intl

Feb 19

ORD7:30 amChicago O'Hare Intl

2h 19m

BOS10:49 amBoston Logan Intl

$122

Find similar

United Airlines

Nov 5

BOS4:15 pmBoston Logan Intl

2h 55m

ORD6:10 pmChicago O'Hare Intl

Nov 6

ORD6:15 amChicago O'Hare Intl

2h 15m

BOS9:30 amBoston Logan Intl

$127

Find similar

United Airlines

Dec 24

BOS4:15 pmBoston Logan Intl

3h 04m

ORD6:19 pmChicago O'Hare Intl

Dec 31

ORD6:11 pmChicago O'Hare Intl

2h 33m

BOS9:44 pmBoston Logan Intl

$131

Find similar

JetBlue flights from Boston to Illinois

Our best JetBlue deals on Boston to Illinois flight tickets

JetBlue

Nov 15

BOS7:10 amBoston Logan Intl

3h 05m

ORD9:15 amChicago O'Hare Intl

Nov 17

ORD6:55 pmChicago O'Hare Intl

2h 32m

BOS10:27 pmBoston Logan Intl

$127

Find similar

JetBlue

Nov 13

BOS8:30 amBoston Logan Intl

3h 05m

ORD10:35 amChicago O'Hare Intl

Nov 15

ORD10:00 amChicago O'Hare Intl

2h 20m

BOS1:20 pmBoston Logan Intl

$130

Find similar

JetBlue

Jan 15

BOS3:35 pmBoston Logan Intl

3h 09m

ORD5:44 pmChicago O'Hare Intl

Jan 20

ORD10:45 amChicago O'Hare Intl

2h 24m

BOS2:09 pmBoston Logan Intl

$132

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 12/4

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

dom. 12/7

7:10 am-10:36 am

Nonstop2h 26m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 12/4

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

dom. 12/7

7:10 am-10:36 am

Nonstop2h 26m

$119

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 11/17

10:40 am-12:40 pm

Nonstop3h 00m

Chicago O'Hare Intl

jue. 2/19

7:30 am-10:49 am

Nonstop2h 19m

$122

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

dom. 11/9

5:15 am-7:00 am

Nonstop2h 45m

Chicago Midway

lun. 11/10

9:35 am-12:50 pm

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 11/15

7:10 am-9:15 am

Nonstop3h 05m

Chicago O'Hare Intl

lun. 11/17

6:55 pm-10:27 pm

Nonstop2h 32m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 11/13

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

sáb. 11/15

10:00 am-1:20 pm

Nonstop2h 20m

$130

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 12/24

4:15 pm-6:19 pm

Nonstop3h 04m

Chicago O'Hare Intl

mié. 12/31

6:11 pm-9:44 pm

Nonstop2h 33m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 1/16

7:00 am-9:05 am

Nonstop3h 05m

Chicago O'Hare Intl

lun. 1/19

1:25 pm-4:43 pm

Nonstop2h 18m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

dom. 11/9

5:15 am-7:00 am

Nonstop2h 45m

Chicago Midway

lun. 11/10

5:15 pm-10:55 pm

1 stop4h 40m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 11/10

5:22 pm-7:36 pm

Nonstop3h 14m

Chicago O'Hare Intl

mar. 11/11

7:00 am-10:25 am

Nonstop2h 25m

$146

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Boston to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Boston is in September. Flight prices, which tend to average around $187, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $193.

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

The cheapest day to depart from Boston to Illinois is on a Wednesday when prices can be found for as low as $322. Flights from Boston to Illinois on a Sunday will generally be more expensive and average around $431. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Boston to Illinois during this time can be as low as $272. Flights in the morning are often more expensive with an average ticket price of $351.

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

Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - Illinois flight prices

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

You are more likely to see cheaper flights to Illinois from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $250 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Boston for as low as $225 on momondo.

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

There are 4 cabin classes available to choose from on Boston Logan Intl to Illinois 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 Illinois flights?

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

Cheap Boston to Illinois flight deals and tips

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

Best Price Found	$131
Fastest flight time	2h 40m
Direct flights	Every day
Airports in Illinois	1 airport

The best one-way flight to Illinois from Boston in the past 72 hours is $131. The best round-trip flight deal from Boston to Illinois found on momondo in the last 72 hours is $200.

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

Direct flights go from Boston to Illinois every day.

There is 1 airport near Illinois: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Boston Logan Intl Airport to Illinois?
Prices for flights from Boston Logan Intl Airport to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Boston Logan Intl Airport to Illinois?
The number of operators available for flights from Boston Logan Intl Airport to Illinois is 7 as of October 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Illinois?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Boston Logan Intl Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The necessary travel and health documents for your Illinois 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 Illinois?
momondo data reveals that the most frequently booked plane model on the route from Boston to Illinois is Boeing 737-800, representing 25.93% of all bookings. The subsequent popular models are Boeing 737-900 at 12.17%, Boeing 737 MAX 8 at 11.41%, and Airbus A220-300 at 9.80%.

Best airlines flying from Boston to Illinois

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $67	Free Cancellation	Rating 6.3 8,115 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $75	Free Cancellation	Rating 7.2 2,906 reviews	Search JetBlue flights
Frontier	PriceFrom $89	Free Cancellation	Rating 5.8 3,123 reviews	Search Frontier flights
Delta	PriceFrom $116	Free Cancellation	Rating 7.9 7,993 reviews	Search Delta flights
Southwest	PriceFrom $117	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
United Airlines	PriceFrom $129	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines flights
American Airlines	PriceFrom $136	Free Cancellation	Rating 7.2 11,030 reviews	Search American Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Boston to Illinois for you.

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

All flight searches from Boston to Illinois on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Boston to Illinois.

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

Price alerts on flights to Illinois 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 Illinois 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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sáb. 11/29

sáb. 12/6

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Find better results for your trip to Illinois

Popular cities in Illinois

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Cheap flights from Boston to Illinois from $60

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 Illinois departing on 11/15. 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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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Find the cheapest flights from Boston to Illinois

Cheap round-trip flights

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United Airlines flights from Boston to Illinois

Our best United Airlines deals on Boston to Illinois flight tickets

JetBlue flights from Boston to Illinois

Our best JetBlue deals on Boston to Illinois flight tickets

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

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How to get the cheapest flight ticket from Boston to Illinois

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 Illinois?

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

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

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Boston to Illinois during this time can be as low as $272. Flights in the morning are often more expensive with an average ticket price of $351.

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

Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - Illinois flight prices

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

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

There are 4 cabin classes available to choose from on Boston Logan Intl to Illinois 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 Illinois flights?

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

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

JetBlue, Frontier, and Southwest are the most popular carriers operating from Boston Logan Intl to Illinois

What airlines fly to Illinois?

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

22 flights are operational daily from Boston to Illinois as of October 2025. The most popular departure time for this route is 4:00PM, with 47% of flights per day taking off in the afternoon.

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

As of October 2025, 159 flights take off from Boston and land in Illinois each week. The most common flight departure day for this route is Thu, with 50% of weekly flights taking off on this day.

Cheap Boston to Illinois flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Illinois

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

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

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

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

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

Best airlines flying from Boston to Illinois

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

Why use momondo?

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

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

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

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

An easier way to manage your Illinois 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.

Find better results for your trip to Illinois

Popular cities in Illinois

Popular flights according to clicks in the last 7 days on momondo