Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Massachusetts to Illinois from $45

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Illinois departing on 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Massachusetts to Illinois

Cheap round-trip flights

These are some of the best round-trip flight deals from Massachusetts to Illinois that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Massachusetts to Illinois.

Cheap last minute flights

Planning a quick getaway from Massachusetts to Illinois? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Illinois, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Massachusetts to Illinois

Find recent round-trip train or bus tickets from Massachusetts to Illinois.

All round-trip flight deals to Illinois

The cheapest plane tickets to Illinois found on KAYAK recently.
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
$98Frontier
Find Deal
Tue, Feb 4 - Wed, Feb 12
6:00 am - 12:45 pmBOS-ORD
7h 45m1 stop
2:59 pm - 12:39 amORD-BOS
8h 40m1 stop
$99Frontier
Find Deal
Wed, Feb 5 - Tue, Feb 11
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$135Delta
Find Deal
Tue, Jan 28 - Thu, Jan 30
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
8:20 pm - 11:44 pmORD-BOS
2h 24mnonstop
$136American Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 4
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$137JetBlue
Find Deal
Tue, Feb 4 - Wed, Feb 12
4:17 pm - 10:00 pmBOS-ORD
6h 43m1 stop
9:20 am - 12:43 pmORD-BOS
2h 23mnonstop
$143United Airlines
Find Deal
Mon, Mar 10 - Wed, Mar 12
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$147JetBlue
Find Deal
Fri, Feb 7 - Tue, Feb 11
7:15 am - 9:21 amBOS-ORD
3h 06mnonstop
6:25 pm - 10:04 pmORD-BOS
2h 39mnonstop
$158Delta
Find Deal
Tue, Feb 11 - Wed, Feb 19
6:00 am - 8:04 amBOS-ORD
3h 04mnonstop
9:12 am - 3:19 pmORD-BOS
5h 07m1 stop
$188United Airlines
Find Deal
Fri, Mar 28 - Tue, Apr 1
5:20 am - 7:21 amBOS-ORD
3h 01mnonstop
12:20 pm - 3:38 pmORD-BOS
2h 18mnonstop
$189American Airlines
Find Deal
Thu, Feb 13 - Wed, Feb 19
6:00 am - 2:43 pmBOS-STL
9h 43m1 stop
$45Spirit Airlines
Find Deal
Tue, Feb 4
6:25 am - 4:10 pmBOS-ORD
10h 45m1 stop
$45Spirit Airlines
Find Deal
Wed, Feb 5
11:45 am - 1:46 pmBOS-ORD
3h 01mnonstop
$69Delta
Find Deal
Wed, Feb 12
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
$79JetBlue
Find Deal
Thu, Jan 23
12:25 pm - 2:27 pmBOS-ORD
3h 02mnonstop
$89United Airlines
Find Deal
Fri, Feb 28
9:20 am - 11:22 amBOS-ORD
3h 02mnonstop
$90United Airlines
Find Deal
Wed, Feb 19
7:00 am - 9:09 amBOS-ORD
3h 09mnonstop
$119Delta
Find Deal
Sat, Mar 15
7:19 pm - 9:15 pmBOS-ORD
2h 56mnonstop
$120American Airlines
Find Deal
Sat, Jun 28
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
$124JetBlue
Find Deal
Fri, Jan 24
12:36 pm - 4:20 pmBOS-ORD
4h 44m1 stop
$129American Airlines
Find Deal
Fri, Apr 4
6:00 am - 11:47 amBOS-ORD
6h 47m1 stop
4:41 pm - 12:39 amORD-BOS
6h 58m1 stop
$136Frontier
Find Deal
Wed, Jan 15 - Thu, Jan 16
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$137JetBlue
Find Deal
Sat, Jan 18 - Tue, Jan 21
6:00 am - 8:03 amBOS-ORD
3h 03mnonstop
12:51 pm - 6:26 pmORD-BOS
4h 35m1 stop
$157United Airlines
Find Deal
Thu, Jan 16 - Thu, Jan 16
8:45 am - 10:45 amBOS-ORD
3h 00mnonstop
6:30 am - 10:03 amORD-BOS
2h 33mnonstop
$167American Airlines
Find Deal
Thu, Jan 16 - Mon, Jan 20
8:45 am - 10:45 amBOS-ORD
3h 00mnonstop
6:30 am - 10:03 amORD-BOS
2h 33mnonstop
$168American Airlines
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:25 am - 4:10 pmBOS-ORD
10h 45m1 stop
6:55 am - 4:59 pmORD-BOS
9h 04m1 stop
$176Spirit Airlines
Find Deal
Sun, Jan 19 - Thu, Jan 23
6:25 am - 4:10 pmBOS-ORD
10h 45m1 stop
12:25 pm - 11:35 pmORD-BOS
10h 10m1 stop
$188Spirit Airlines
Find Deal
Sun, Jan 19 - Fri, Jan 24
5:45 pm - 7:52 pmBOS-ORD
3h 07mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$202Delta
Find Deal
Sat, Jan 18 - Mon, Jan 20
10:35 am - 4:26 pmBOS-ORD
6h 51m1 stop
9:20 am - 12:46 pmORD-BOS
2h 26mnonstop
$208United Airlines
Find Deal
Sat, Jan 18 - Mon, Jan 20
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
7:30 am - 1:23 pmORD-BOS
4h 53m1 stop
$242Delta
Find Deal
Thu, Jan 16 - Sun, Jan 19
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$135Delta
Find Deal
Tue, Jan 28 - Thu, Jan 30
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
8:20 pm - 11:44 pmORD-BOS
2h 24mnonstop
$136American Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 4
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$137JetBlue
Find Deal
Tue, Feb 4 - Tue, Feb 11
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
Wed, Jan 29 - Thu, Jan 30
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$147JetBlue
Find Deal
Fri, Feb 7 - Tue, Feb 11
6:35 pm - 8:25 pmBOS-MDW
2h 50mnonstop
9:00 am - 12:15 pmMDW-BOS
2h 15mnonstop
$147Southwest
Find Deal
Fri, Feb 7 - Sat, Feb 8
7:15 am - 9:21 amBOS-ORD
3h 06mnonstop
6:25 pm - 10:04 pmORD-BOS
2h 39mnonstop
$158Delta
Find Deal
Tue, Feb 11 - Wed, Feb 19
12:25 pm - 2:27 pmBOS-ORD
3h 02mnonstop
9:15 am - 12:38 pmORD-BOS
2h 23mnonstop
$168United Airlines
Find Deal
Fri, Feb 21 - Tue, Feb 25
9:30 am - 11:28 amBOS-ORD
2h 58mnonstop
7:30 am - 10:49 amORD-BOS
2h 19mnonstop
$178United Airlines
Find Deal
Sun, Feb 9 - Thu, Feb 13
6:00 am - 8:15 amBOS-ORD
3h 15mnonstop
12:20 pm - 3:38 pmORD-BOS
2h 18mnonstop
$179American Airlines
Find Deal
Tue, Feb 18 - Wed, Feb 19

Delta flights from Massachusetts to Illinois

Our best Delta deals on Massachusetts to Illinois flight tickets
Delta
Jan 28
BOS3:30 pmBoston Logan Intl
3h 06m
ORD5:36 pmChicago O'Hare Intl
Jan 30
ORD7:10 amChicago O'Hare Intl
2h 37m
BOS10:47 amBoston Logan Intl
Delta
Jan 21
BOS3:30 pmBoston Logan Intl
3h 06m
ORD5:36 pmChicago O'Hare Intl
Jan 23
ORD7:10 amChicago O'Hare Intl
2h 37m
BOS10:47 amBoston Logan Intl
Delta
Feb 11
BOS7:15 amBoston Logan Intl
3h 06m
ORD9:21 amChicago O'Hare Intl
Feb 19
ORD6:25 pmChicago O'Hare Intl
2h 39m
BOS10:04 pmBoston Logan Intl

United Airlines flights from Massachusetts to Illinois

Our best United Airlines deals on Massachusetts to Illinois flight tickets
United Airlines
Mar 10
BOS4:17 pmBoston Logan Intl
6h 43m
1 stop
ORD10:00 pmChicago O'Hare Intl
Mar 12
ORD9:20 amChicago O'Hare Intl
2h 23m
BOS12:43 pmBoston Logan Intl
United Airlines
Jan 20
BOS5:45 amBoston Logan Intl
4h 59m
1 stop
ORD9:44 amChicago O'Hare Intl
Jan 21
ORD11:51 amChicago O'Hare Intl
4h 21m
1 stop
BOS5:12 pmBoston Logan Intl
United Airlines
Mar 28
BOS6:00 amBoston Logan Intl
3h 04m
ORD8:04 amChicago O'Hare Intl
Apr 1
ORD9:12 amChicago O'Hare Intl
5h 07m
1 stop
BOS3:19 pmBoston Logan Intl

See travel insights to Illinois from

How to get the cheapest flight ticket from Massachusetts 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?

The cheapest month to fly to Illinois from Massachusetts is in September. Flight prices, which tend to average around $183, 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 $191.

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

The cheapest day to depart from Massachusetts to Illinois is on a Tuesday when prices can be found for as low as $222. Flights from Massachusetts to Illinois on a Sunday will generally be more expensive and average around $278. 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 Massachusetts to Illinois during this time can be as low as $237. Flights in the afternoon are often more expensive with an average ticket price of $277.

What is the cheapest Massachusetts to Illinois flight route?

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

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

The best time to book a flight to Illinois from Massachusetts is 57 days out, which is when prices tend to be around $247. In the past 72 hours, momondo users found flights from Massachusetts to Illinois for as low as $163.

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

There are 4 cabin classes available to choose from on Massachusetts to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Massachusetts to Illinois flight deals and tips

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

Best Price Found

$45

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Illinois

3 airports
The best one-way flight to Illinois from Massachusetts in the past 72 hours is $45. The best round-trip flight deal from Massachusetts to Illinois found on momondo in the last 72 hours is $98.
The fastest flight from Massachusetts to Illinois takes 2h 10m
Direct flights go from Massachusetts to Illinois every day.
There are 3 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Lambert-St Louis (STL)

  • When did momondo last update prices for flights from Massachusetts to Illinois?

    Prices for flights from Massachusetts to Illinois refresh daily.

  • How many operators does momondo search for flights from Massachusetts to Illinois?

  • How old do you have to be to fly from Massachusetts to Illinois?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Illinois.

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

    The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Massachusetts to Illinois?


Best airlines flying from Massachusetts to Illinois

Compare and see reviews for airlines that fly from Massachusetts to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $39Free CancellationRating
6.3
8,089 reviews
Search Spirit Airlines flights
JetBluePriceFrom $81Free CancellationRating
7.4
3,196 reviews
Search JetBlue flights
DeltaPriceFrom $93Free CancellationRating
8.0
8,508 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.0
3,431 reviews
Search Frontier flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
8,961 reviews
Search United Airlines flights
SouthwestPriceFrom $149Free CancellationRating
8.1
4,659 reviews
Search Southwest flights

Why use momondo?

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

It is quick and easy to find Massachusetts to Illinois 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 Illinois that suits you.

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

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

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

Once all potential Massachusetts to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Massachusetts to Illinois flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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.
1 adult
From?
To?
Sun 1/19
Sun 1/26
Email me momondo's favorite deals

Find better results for your trip to Illinois

Popular cities in Illinois

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