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Cheap flights from Boston 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 Boston 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

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Find the cheapest flights from Boston to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:01 pm - 10:02 pm
BOS
-
MDW
11h 01m
1 stop
Frontier Logo
6:00 am - 1:27 am
MDW
-
BOS
18h 27m
1 stop
$169Frontier
Wed, Jun 3 - Wed, Jun 10
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
$176JetBlue
Thu, May 28 - Sun, May 31
Delta Logo
5:30 pm - 7:33 pm
BOS
-
ORD
3h 03mnonstop
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
$183Delta
Sat, May 30 - Sun, May 31
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
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
$187Southwest
Wed, Jun 3 - Tue, Jun 9
United Airlines Logo
6:40 pm - 8:40 pm
BOS
-
ORD
3h 00mnonstop
United Airlines Logo
6:05 am - 9:29 am
ORD
-
BOS
2h 24mnonstop
$192United Airlines
Sat, May 30 - Tue, Jun 2
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
$192Southwest
Wed, Jun 3 - Tue, Jun 9
American Airlines Logo
3:00 pm - 9:08 pm
BOS
-
CMI
7h 08m
1 stop
American Airlines Logo
6:43 pm - 12:28 am
CMI
-
BOS
4h 45m
1 stop
$306American Airlines
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
5:10 am - 9:17 am
BOS
-
PIA
5h 07m
1 stop
American Airlines Logo
4:22 pm - 12:37 am
PIA
-
BOS
7h 15m
1 stop
$319American Airlines
Wed, Jul 8 - Wed, Jul 15
Delta Logo
5:35 am - 10:20 am
BOS
-
MLI
5h 45m
1 stop
Delta Logo
5:17 pm - 1:28 am
MLI
-
BOS
7h 11m
1 stop
$347Delta
Thu, May 28 - Mon, Jun 1

Delta flights from Boston to Illinois

Our best Delta deals on Boston to Illinois flight tickets
Delta
May 30
BOS5:30 pmBoston Logan Intl
3h 03m
ORD7:33 pmChicago O'Hare Intl
May 31
ORD7:00 amChicago O'Hare Intl
2h 35m
BOS10:35 amBoston Logan Intl
$183
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 27
BOS8:40 pmBoston Logan Intl
2h 55m
ORD10:35 pmChicago O'Hare Intl
Jun 6
ORD4:30 pmChicago O'Hare Intl
2h 36m
BOS8:06 pmBoston Logan Intl
$192

JetBlue flights from Boston to Illinois

Our best JetBlue deals on Boston to Illinois flight tickets
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
May 26
BOS5:25 pmBoston Logan Intl
3h 10m
ORD7:35 pmChicago O'Hare Intl
May 27
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$179
JetBlue
May 26
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
May 27
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$182

momondo Fare Finder

 
Customize your flight search to find flights from Boston 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 15, 2026.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 6/3

12:01 pm-10:02 pm

1 stop11h 01m

Chicago Midway

Wed 6/10

6:00 am-1:27 am

1 stop18h 27m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/28

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 5/31

8:30 pm-11:59 pm

Nonstop2h 29m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

5:30 pm-7:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sun 5/31

7:00 am-10:35 am

Nonstop2h 35m

$183

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

Wed 6/3

7:20 am-9:05 am

Nonstop2h 45m

Chicago Midway

Tue 6/9

9:00 am-12:15 pm

Nonstop2h 15m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

6:40 pm-8:40 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 6/2

6:05 am-9:29 am

Nonstop2h 24m

$192
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 6/3

10:45 am-12:25 pm

Nonstop2h 40m

Chicago Midway

Tue 6/9

9:00 am-12:15 pm

Nonstop2h 15m

$192

BostonChampaign

BOS - CMI

BOSCMI

Boston Logan Intl

Wed 6/3

3:00 pm-9:08 pm

1 stop7h 08m

Champaign University-Willard

Wed 6/10

6:43 pm-12:28 am

1 stop4h 45m

$306

BostonPeoria

BOS - PIA

BOSPIA

Boston Logan Intl

Wed 7/8

5:10 am-9:17 am

1 stop5h 07m

Greater Peoria

Wed 7/15

4:22 pm-12:37 am

1 stop7h 15m

$319

BostonMoline

BOS - MLI

BOSMLI

Boston Logan Intl

Thu 5/28

5:35 am-10:20 am

1 stop5h 45m

Moline Quad-City

Mon 6/1

5:17 pm-1:28 am

1 stop7h 11m

$347

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

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?

The cheapest month to fly to Illinois from Boston 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 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 $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 Boston 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 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 $249 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 $207 on momondo.

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

$130

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 $130. The best round-trip flight deal from Boston to Illinois found on momondo in the last 72 hours is $233.
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), Lambert-St Louis (STL).
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?

  • 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?

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
JetBluePriceFrom $68Free CancellationRating
7.1
2,974 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,456 reviews
Search Delta flights
Spirit AirlinesPriceFrom $95Free CancellationRating
6.2
8,626 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $120Free CancellationRating
7.4
9,721 reviews
Search United Airlines flights
SouthwestPriceFrom $127Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
American AirlinesPriceFrom $136Free CancellationRating
7.1
11,665 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

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