Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Massachusetts to Illinois from $81

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 6/9. 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

Discover deals from 900+ travel sites with momondo.

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.
Search flight deals

Find the cheapest flights from Massachusetts to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
$173JetBlue
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
5:20 am - 6:55 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
2:40 pm - 6:00 pm
MDW
-
BOS
2h 20mnonstop
$176Southwest
Sat, Jun 6 - Tue, Jun 9
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
9:41 pm - 1:14 am
ORD
-
BOS
2h 33mnonstop
$187United Airlines
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
9:10 am - 10:11 pm
BOS
-
MDW
14h 01m
1 stop
Frontier Logo
6:00 am - 1:27 am
MDW
-
BOS
18h 27m
1 stop
$189Frontier
Tue, Jun 9 - Wed, Jun 10
Frontier Logo
6:00 am - 11:12 am
BOS
-
MDW
6h 12m
1 stop
Frontier Logo
12:04 pm - 1:27 am
MDW
-
BOS
12h 23m
1 stop
$190Frontier
Tue, Aug 25 - Wed, Aug 26
American Airlines Logo
8:57 am - 11:00 am
BOS
-
ORD
3h 03mnonstop
American Airlines Logo
8:59 pm - 12:28 am
ORD
-
BOS
2h 29mnonstop
$191American Airlines
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
6:00 am - 7:58 am
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
7:33 am - 11:05 am
ORD
-
BOS
2h 32mnonstop
$192United Airlines
Mon, Jun 1 - Wed, Jun 3
American Airlines Logo
8:13 pm - 10:00 pm
ALB
-
ORD
2h 47mnonstop
American Airlines Logo
4:24 pm - 7:40 pm
ORD
-
ALB
2h 16mnonstop
$319American Airlines
Thu, Aug 13 - Mon, Aug 17
Delta Logo
6:00 am - 8:42 am
ALB
-
MDW
3h 42m
1 stop
Delta Logo
5:59 pm - 11:06 pm
MDW
-
ALB
4h 07m
1 stop
$332Delta
Wed, Sep 16 - Mon, Sep 21
Delta Logo
6:06 am - 9:32 am
ALB
-
STL
4h 26m
1 stop
Delta Logo
4:00 pm - 11:59 pm
STL
-
ALB
6h 59m
1 stop
$335Delta
Thu, Jun 11 - Sat, Jun 13

JetBlue flights from Massachusetts to Illinois

Our best JetBlue deals on Massachusetts to Illinois flight tickets
JetBlue
Jun 2
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
Jun 9
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$173
JetBlue
May 28
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
May 31
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$176
JetBlue
Jun 2
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
Jun 9
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$182

Delta flights from Massachusetts to Illinois

Our best Delta deals on Massachusetts to Illinois flight tickets
Delta
May 27
BOS4:15 pmBoston Logan Intl
3h 00m
ORD6:15 pmChicago O'Hare Intl
Jun 3
ORD7:00 amChicago O'Hare Intl
2h 35m
BOS10:35 amBoston Logan Intl
$187
Delta
May 30
BOS5:30 pmBoston Logan Intl
3h 03m
ORD7:33 pmChicago O'Hare Intl
Jun 6
ORD7:00 amChicago O'Hare Intl
2h 35m
BOS10:35 amBoston Logan Intl
$197
Delta
May 27
BOS4:15 pmBoston Logan Intl
3h 00m
ORD6:15 pmChicago O'Hare Intl
May 31
ORD7:00 amChicago O'Hare Intl
2h 35m
BOS10:35 amBoston Logan Intl
$212

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 18, 2026.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/2

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Tue 6/9

8:30 pm-11:59 pm

Nonstop2h 29m

$173
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 6/6

5:20 am-6:55 am

Nonstop2h 35m

Chicago Midway

Tue 6/9

2:40 pm-6:00 pm

Nonstop2h 20m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/3

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Tue 6/9

9:41 pm-1:14 am

Nonstop2h 33m

$187

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 6/9

9:10 am-10:11 pm

1 stop14h 01m

Chicago Midway

Wed 6/10

6:00 am-1:27 am

1 stop18h 27m

$189

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 8/25

6:00 am-11:12 am

1 stop6h 12m

Chicago Midway

Wed 8/26

12:04 pm-1:27 am

1 stop12h 23m

$190

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/2

8:57 am-11:00 am

Nonstop3h 03m

Chicago O'Hare Intl

Mon 6/8

8:59 pm-12:28 am

Nonstop2h 29m

$191

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 6/1

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Wed 6/3

7:33 am-11:05 am

Nonstop2h 32m

$192

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Thu 8/13

8:13 pm-10:00 pm

Nonstop2h 47m

Chicago O'Hare Intl

Mon 8/17

4:24 pm-7:40 pm

Nonstop2h 16m

$319

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 9/16

6:00 am-8:42 am

1 stop3h 42m

Chicago Midway

Mon 9/21

5:59 pm-11:06 pm

1 stop4h 07m

$332

AlbanySt. Louis

ALB - STL

ALBSTL

Albany Intl

Thu 6/11

6:06 am-9:32 am

1 stop4h 26m

Lambert-St Louis

Sat 6/13

4:00 pm-11:59 pm

1 stop6h 59m

$335

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $169, 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 February is also cheap. Prices for this month can be found on momondo for an average of $205.

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

The cheapest day to depart from Massachusetts to Illinois is on a Friday when prices can be found for as low as $318. Flights from Massachusetts to Illinois on a Sunday will generally be more expensive and average around $412. 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 $270. Flights at noon are often more expensive with an average ticket price of $364.

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

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

You are more likely to see cheaper flights to Illinois from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $249 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Massachusetts for as low as $207 on momondo.

Can stopping save me money on Massachusetts to Illinois flights?

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

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

$130

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Massachusetts in the past 72 hours is $130. The best round-trip flight deal from Massachusetts to Illinois found on momondo in the last 72 hours is $233.
The fastest flight from Massachusetts to Illinois takes 2h 05m
Direct flights go from Massachusetts to Illinois every day.
There are 98 airports in Illinois. From Massachusetts there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Massachusetts to Illinois

  • 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
JetBluePriceFrom $68Free CancellationRating
7.1
2,979 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,449 reviews
Search Delta flights
Spirit AirlinesPriceFrom $95Free CancellationRating
6.2
8,621 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $120Free CancellationRating
7.4
9,737 reviews
Search United Airlines flights
SouthwestPriceFrom $127Free CancellationRating
7.9
4,289 reviews
Search Southwest flights
American AirlinesPriceFrom $136Free CancellationRating
7.1
11,650 reviews
Search American Airlines 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 6/17
Wed 6/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Illinois

Popular cities in Illinois

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $88
Flights to Los Angelesfrom $47
Flights to Orlandofrom $58
Flights to Miamifrom $55
Flights to Chicagofrom $62
Flights to San Franciscofrom $54
Flights to Las Vegasfrom $48
Flights to Washington, D.C.from $56
Flights to Bostonfrom $63
Flights to Atlantafrom $54
Flights to Fort Lauderdalefrom $56
Flights to Dallasfrom $96