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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 12/17. 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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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 - 5:54 pmBOS-MDW
12h 54m1 stop
10:50 am - 12:39 amMDW-BOS
12h 49m1 stop
$100Frontier
Find Deal
Tue, Dec 17 - Wed, Dec 18
5:45 am - 4:33 pmBOS-ORD
11h 48m1 stop
10:22 pm - 7:33 amORD-BOS
8h 11m1 stop
$100Frontier
Find Deal
Tue, Dec 17 - Wed, Dec 18
2:18 pm - 10:59 pmBOS-ORD
9h 41m1 stop
8:00 am - 3:27 pmORD-BOS
6h 27m1 stop
$105Spirit Airlines
Find Deal
Tue, Dec 17 - Wed, Jan 15
2:18 pm - 10:59 pmBOS-ORD
9h 41m1 stop
10:22 pm - 7:33 amORD-BOS
8h 11m1 stop
Tue, Dec 17 - Wed, Dec 25
6:00 am - 1:34 pmBOS-ORD
8h 34m1 stop
8:14 pm - 9:58 amORD-BOS
12h 44m1 stop
Tue, Jan 7 - Tue, Jan 7
10:00 am - 4:10 pmBOS-ORD
7h 10m1 stop
8:00 am - 6:03 pmORD-BOS
9h 03m1 stop
$119Spirit Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Fri, Dec 13 - Sat, Dec 14
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$158JetBlue
Find Deal
Thu, Dec 12 - Mon, Dec 16
7:38 pm - 11:20 pmBOS-ORD
4h 42m1 stop
8:48 am - 2:32 pmORD-BOS
4h 44m1 stop
$176United Airlines
Find Deal
Mon, Dec 9 - Wed, Dec 11
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
6:25 pm - 9:54 pmORD-BOS
2h 29mnonstop
$194United Airlines
Find Deal
Wed, Jan 1 - Sun, Jan 5
12:00 pm - 10:59 pmBOS-ORD
11h 59m1 stop
$45Spirit Airlines
Find Deal
Tue, Dec 17
2:18 pm - 10:59 pmBOS-ORD
9h 41m1 stop
$46Spirit Airlines
Find Deal
Tue, Dec 17
8:01 am - 1:09 pmBOS-MDW
6h 08m1 stop
$52Frontier
Find Deal
Tue, Dec 17
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$53Frontier
Find Deal
Wed, Dec 11
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
$78Delta
Find Deal
Thu, Dec 5
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$79Delta
Find Deal
Fri, Jan 31
5:50 pm - 10:57 pmBOS-ORD
6h 07m1 stop
$88United Airlines
Find Deal
Sun, Jan 12
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$95United Airlines
Find Deal
Wed, Jan 1
5:38 am - 10:59 amBOS-ORD
6h 21m1 stop
$98JetBlue
Find Deal
Tue, Mar 11
6:00 am - 8:07 amBOS-ORD
3h 07mnonstop
$100JetBlue
Find Deal
Fri, Jan 3
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
10:59 am - 12:30 amORD-BOS
12h 31m1 stop
Thu, Nov 28 - Fri, Dec 13
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
10:59 am - 12:30 amORD-BOS
12h 31m1 stop
Fri, Nov 29 - Mon, Dec 9
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
8:02 pm - 9:02 amORD-BOS
12h 00m1 stop
$206Spirit Airlines
Find Deal
Mon, Dec 2 - Sat, Dec 7
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
7:39 pm - 9:14 amORD-BOS
12h 35m1 stop
$219Spirit Airlines
Find Deal
Thu, Nov 28 - Tue, Dec 3
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
$261United Airlines
Find Deal
Mon, Dec 2 - Fri, Dec 6
11:35 am - 9:59 pmBOS-MDW
11h 24m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$278Frontier
Find Deal
Thu, Nov 28 - Wed, Dec 4
6:59 pm - 9:06 pmBOS-ORD
3h 07mnonstop
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
$282JetBlue
Find Deal
Fri, Nov 29 - Wed, Dec 4
6:59 pm - 9:06 pmBOS-ORD
3h 07mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$292JetBlue
Find Deal
Fri, Nov 29 - Sun, Dec 15
12:37 pm - 7:32 pmBOS-MDW
7h 55m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$301Frontier
Find Deal
Mon, Dec 2 - Tue, Dec 10
2:55 pm - 7:48 amBDL-ORD
17h 53m2 stops
10:55 am - 2:07 pmORD-BDL
2h 12mnonstop
$318United Airlines
Find Deal
Thu, Nov 28 - Fri, Nov 29
11:05 am - 1:00 pmBOS-ORD
2h 55mnonstop
2:05 pm - 5:34 pmORD-BOS
2h 29mnonstop
$156Delta
Find Deal
Tue, Dec 10 - Tue, Dec 17
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Fri, Dec 13 - Tue, Dec 17
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$158Southwest
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$158JetBlue
Find Deal
Thu, Dec 12 - Mon, Dec 16
2:52 pm - 4:52 pmBOS-ORD
3h 00mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$159American Airlines
Find Deal
Fri, Jan 10 - Fri, Jan 17
6:10 am - 8:14 amBOS-ORD
3h 04mnonstop
4:25 pm - 7:49 pmORD-BOS
2h 24mnonstop
$167JetBlue
Find Deal
Sun, Feb 2 - Sat, Mar 1
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$168Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 26
2:52 pm - 4:52 pmBOS-ORD
3h 00mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$187American Airlines
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
6:25 pm - 9:54 pmORD-BOS
2h 29mnonstop
$194United Airlines
Find Deal
Wed, Jan 1 - Sun, Jan 5
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
2:00 pm - 5:23 pmORD-BOS
2h 23mnonstop
$248United Airlines
Find Deal
Sat, Jan 4 - Tue, Jan 7

Delta flights from Massachusetts to Illinois

Our best Delta deals on Massachusetts to Illinois flight tickets
Delta
Dec 5
BOS7:20 amBoston Logan Intl
3h 09m
ORD9:29 amChicago O'Hare Intl
Dec 6
ORD6:50 pmChicago O'Hare Intl
2h 30m
BOS10:20 pmBoston Logan Intl
Delta
Dec 5
BOS7:20 amBoston Logan Intl
3h 09m
ORD9:29 amChicago O'Hare Intl
Dec 9
ORD6:30 amChicago O'Hare Intl
2h 30m
BOS10:00 amBoston Logan Intl
Delta
Dec 5
BOS11:05 amBoston Logan Intl
2h 58m
ORD1:03 pmChicago O'Hare Intl
Dec 9
ORD6:30 amChicago O'Hare Intl
2h 30m
BOS10:00 amBoston Logan Intl

Spirit Airlines flights from Massachusetts to Illinois

Our best Spirit Airlines deals on Massachusetts to Illinois flight tickets
Spirit Airlines
Dec 17
BOS2:18 pmBoston Logan Intl
9h 41m
1 stop
ORD10:59 pmChicago O'Hare Intl
Jan 15
ORD8:00 amChicago O'Hare Intl
6h 27m
1 stop
BOS3:27 pmBoston Logan Intl
Spirit Airlines
Dec 10
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl
Dec 17
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl
Spirit Airlines
Jan 14
BOS10:00 amBoston Logan Intl
7h 10m
1 stop
ORD4:10 pmChicago O'Hare Intl
Jan 21
ORD8:00 amChicago O'Hare Intl
9h 03m
1 stop
BOS6:03 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 $184, 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 $187.

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 $277. 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 $236. Flights in the afternoon are often more expensive with an average ticket price of $274.

What is the cheapest Massachusetts to Illinois flight route?

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

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.

Can stopping save me money on Massachusetts to Illinois flights?

You could potentially save up to 37% on your flight if you consider stops on a Massachusetts to Illinois flight.

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 15m

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 $100.
The fastest flight from Massachusetts to Illinois takes 2h 15m
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
8,172 reviews
Search Spirit Airlines flights
JetBluePriceFrom $82Free CancellationRating
7.4
3,362 reviews
Search JetBlue flights
DeltaPriceFrom $95Free CancellationRating
8.0
8,730 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.1
3,523 reviews
Search Frontier flights
American AirlinesPriceFrom $135Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
9,146 reviews
Search United Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.1
4,979 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.


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