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

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

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

48 flights are operational daily from Boston to Illinois as of August 2026. The most popular departure time for this route is 8:00AM, with 40% of flights per day taking off at noon.

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 42% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 5 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 week?

As of August 2026, 340 flights take off from Boston and land in Illinois each week. The most common flight departure day for this route is Fri, with 21% of weekly flights taking off on this day.

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 6 as of August 2026.

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.

$97 Cheap Flights from Boston to Illinois in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Boston to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:28 am - 8:28 pm

BOS

ORD

10h 00m

1 stop

9:33 pm - 10:52 am

ORD

BOS

12h 19m

1 stop

$161Frontier

Wed, Oct 21 - Fri, Oct 23

12:45 pm - 8:08 pm

BOS

ORD

8h 23m

1 stop

9:10 pm - 9:09 am

ORD

BOS

10h 59m

1 stop

$161Frontier

Wed, Sep 2 - Fri, Sep 4

6:55 am - 8:49 am

BOS

ORD

2h 54mnonstop

1:00 pm - 8:49 pm

ORD

BOS

6h 49m

1 stop

$199JetBlue

Tue, Oct 6 - Thu, Oct 8

5:00 pm - 7:01 pm

BOS

ORD

3h 01mnonstop

7:00 am - 3:14 pm

ORD

BOS

7h 14m

1 stop

$203JetBlue

Sat, Sep 12 - Sun, Sep 13

7:00 am - 9:06 am

BOS

ORD

3h 06mnonstop

1:54 pm - 5:35 pm

ORD

BOS

2h 41mnonstop

$217American Airlines

Wed, Sep 9 - Sat, Sep 12

4:29 pm - 6:42 pm

BOS

ORD

3h 13mnonstop

5:18 pm - 9:00 pm

ORD

BOS

2h 42mnonstop

$217American Airlines

Sat, Sep 12 - Tue, Sep 15

4:30 pm - 6:28 pm

BOS

ORD

2h 58mnonstop

7:35 am - 11:08 am

ORD

BOS

2h 33mnonstop

$217Delta

Tue, Sep 22 - Wed, Sep 30

12:15 pm - 2:04 pm

BOS

ORD

2h 49mnonstop

7:30 pm - 11:09 pm

ORD

BOS

2h 39mnonstop

$217Delta

Wed, Sep 23 - Tue, Sep 29

10:55 am - 12:30 pm

BOS

MDW

2h 35mnonstop

8:15 am - 11:35 am

MDW

BOS

2h 20mnonstop

$217Southwest

Wed, Oct 28 - Sat, Oct 31

10:05 am - 11:35 am

BOS

MDW

2h 30mnonstop

7:40 am - 11:00 am

MDW

BOS

2h 20mnonstop

$217Southwest

Wed, Sep 16 - Sat, Sep 19

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Frontier flights from Boston to Illinois

Our best Frontier deals on Boston to Illinois flight tickets

Frontier

Oct 21

BOS11:28 amBoston Logan Intl

10h 00m

1 stop

ORD8:28 pmChicago O'Hare Intl

Oct 23

ORD9:33 pmChicago O'Hare Intl

12h 19m

1 stop

BOS10:52 amBoston Logan Intl

$161

Frontier

Aug 26

BOS12:45 pmBoston Logan Intl

8h 23m

1 stop

ORD8:08 pmChicago O'Hare Intl

Sep 2

ORD7:44 pmChicago O'Hare Intl

12h 25m

1 stop

BOS9:09 amBoston Logan Intl

$166

Frontier

Aug 29

BOS12:45 pmBoston Logan Intl

8h 23m

1 stop

ORD8:08 pmChicago O'Hare Intl

Sep 5

ORD7:44 pmChicago O'Hare Intl

12h 25m

1 stop

BOS9:09 amBoston Logan Intl

$167

American Airlines flights from Boston to Illinois

Our best American Airlines deals on Boston to Illinois flight tickets

American Airlines

Sep 12

BOS12:05 pmBoston Logan Intl

3h 02m

ORD2:07 pmChicago O'Hare Intl

Sep 14

ORD5:18 pmChicago O'Hare Intl

2h 42m

BOS9:00 pmBoston Logan Intl

$228

American Airlines

Aug 14

BOS7:39 pmBoston Logan Intl

5h 20m

1 stop

ORD11:59 pmChicago O'Hare Intl

Aug 22

ORD5:00 amChicago O'Hare Intl

4h 12m

1 stop

BOS10:12 amBoston Logan Intl

$270

American Airlines

Aug 13

BOS7:10 amBoston Logan Intl

3h 06m

ORD9:16 amChicago O'Hare Intl

Aug 16

ORD6:00 amChicago O'Hare Intl

5h 16m

1 stop

BOS12:16 pmBoston Logan Intl

$275

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/21

11:28 am-8:28 pm

1 stop10h 00m

Chicago O'Hare Intl

Fri 10/23

9:33 pm-10:52 am

1 stop12h 19m

$161

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/2

12:45 pm-8:08 pm

1 stop8h 23m

Chicago O'Hare Intl

Fri 9/4

9:10 pm-9:09 am

1 stop10h 59m

$161

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/6

6:55 am-8:49 am

Nonstop2h 54m

Chicago O'Hare Intl

Thu 10/8

1:00 pm-8:49 pm

1 stop6h 49m

$199

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/12

5:00 pm-7:01 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sun 9/13

7:00 am-3:14 pm

1 stop7h 14m

$203

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/9

7:00 am-9:06 am

Nonstop3h 06m

Chicago O'Hare Intl

Sat 9/12

1:54 pm-5:35 pm

Nonstop2h 41m

$217

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/12

4:29 pm-6:42 pm

Nonstop3h 13m

Chicago O'Hare Intl

Tue 9/15

5:18 pm-9:00 pm

Nonstop2h 42m

$217

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/22

4:30 pm-6:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

Wed 9/30

7:35 am-11:08 am

Nonstop2h 33m

$217

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/23

12:15 pm-2:04 pm

Nonstop2h 49m

Chicago O'Hare Intl

Tue 9/29

7:30 pm-11:09 pm

Nonstop2h 39m

$217

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/28

10:55 am-12:30 pm

Nonstop2h 35m

Chicago Midway

Sat 10/31

8:15 am-11:35 am

Nonstop2h 20m

$217

Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 9/16

10:05 am-11:35 am

Nonstop2h 30m

Chicago Midway

Sat 9/19

7:40 am-11:00 am

Nonstop2h 20m

$217

Flights are sorted by cheapest round-trip flights first.

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 January. Flight prices, which tend to average around $197, 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 January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $216.

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

The cheapest day to depart from Boston to Illinois is on a Friday when prices can be found for as low as $316. Flights from Boston to Illinois on a Sunday will generally be more expensive and average around $413. 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 $274. Flights at noon are often more expensive with an average ticket price of $370.

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

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

How far in advance should I book a flight from Boston 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 $252 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 $223 on momondo.

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

There are 4 cabin classes available to choose from on Boston 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	$163
Fastest flight time	2h 30m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Boston in the past 72 hours is $163. The best round-trip flight deal from Boston to Illinois found on momondo in the last 72 hours is $240.

The fastest flight from Boston to Illinois takes 2h 30m

Direct flights go from Boston to Illinois every day.

There are 98 airports in Illinois. From Boston there are direct flights to Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Boston to Illinois

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 6 as of August 2026.
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 18.17% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 11.86%, Airbus A321neo at 11.74%, and Boeing 737-900 at 11.18%.

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
JetBlue	PriceFrom $69	Free Cancellation	Rating 7.1 3,029 reviews	Search JetBlue flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.8 8,494 reviews	Search Delta flights
United Airlines	PriceFrom $126	Free Cancellation	Rating 7.4 10,062 reviews	Search United Airlines flights
Southwest	PriceFrom $134	Free Cancellation	Rating 8.0 4,229 reviews	Search Southwest flights
American Airlines	PriceFrom $137	Free Cancellation	Rating 7.1 11,845 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.

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Popular cities in Illinois

Flights to New Yorkfrom $76

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Flights to Chicagofrom $58

Flights to San Franciscofrom $46

Flights to Las Vegasfrom $46

Flights to Washington, D.C.from $48

Flights to Bostonfrom $51

Flights to Atlantafrom $51

Flights to Fort Lauderdalefrom $46

Flights to Dallasfrom $61

Cheap flights from Boston to Illinois from $98

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 8/23. 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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Frontier flights from Boston to Illinois

Our best Frontier deals on Boston to Illinois flight tickets

American Airlines flights from Boston to Illinois

Our best American Airlines deals on Boston to Illinois flight tickets

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See travel insights to Illinois from

How to get the cheapest flight ticket from Boston to Illinois

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?

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

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

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

Can stopping save me money on Boston to Illinois flights?

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

What airlines fly to Illinois?

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

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

Cheap Boston to Illinois flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Illinois

Frequently asked questions about flying 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?

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

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