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Cheap flights from Illinois to Boston from $88

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Boston 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.
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Find the cheapest flights from Illinois to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 1:27 am
MDW
-
BOS
18h 27m
1 stop
Frontier Logo
6:00 am - 10:11 pm
BOS
-
MDW
17h 11m
1 stop
$169Frontier
Tue, Jun 9 - Wed, Jun 10
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$172JetBlue
Thu, May 28 - Sun, May 31
JetBlue Logo
1:56 pm - 5:27 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$176JetBlue
Sat, May 30 - Sun, May 31
Frontier Logo
6:00 am - 1:27 am
MDW
-
BOS
18h 27m
1 stop
Frontier Logo
6:00 am - 10:11 pm
BOS
-
MDW
17h 11m
1 stop
$185Frontier
Tue, Jun 9 - Wed, Jun 10
American Airlines Logo
3:15 pm - 6:50 pm
ORD
-
BOS
2h 35mnonstop
American Airlines Logo
7:46 pm - 10:00 pm
BOS
-
ORD
3h 14mnonstop
$186American Airlines
Tue, Jun 9 - Wed, Jun 10
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
Delta Logo
5:30 pm - 7:33 pm
BOS
-
ORD
3h 03mnonstop
$187Delta
Sat, May 30 - Sat, May 30
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$187Southwest
Tue, Jun 9 - Wed, Jun 10
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$192Southwest
Tue, Jun 9 - Tue, Jun 16
American Airlines Logo
6:43 pm - 12:28 am
CMI
-
BOS
4h 45m
1 stop
American Airlines Logo
5:00 am - 11:05 am
BOS
-
CMI
7h 05m
1 stop
$306American Airlines
Sat, Jun 6 - Sat, Jun 13
Delta Logo
5:00 pm - 1:06 am
MLI
-
BOS
7h 06m
1 stop
Delta Logo
4:20 pm - 10:30 pm
BOS
-
MLI
7h 10m
1 stop
$325Delta
Wed, Sep 9 - Wed, Sep 23

Frontier flights from Illinois to Boston

Our best Frontier deals on Illinois to Boston flight tickets
Frontier
Jun 9
MDW6:00 amChicago Midway
18h 27m
1 stop
BOS1:27 amBoston Logan Intl
Jun 10
BOS6:00 amBoston Logan Intl
17h 11m
1 stop
MDW10:11 pmChicago Midway
$169
Frontier
Jun 9
MDW6:00 amChicago Midway
18h 27m
1 stop
BOS1:27 amBoston Logan Intl
Jun 10
BOS6:00 amBoston Logan Intl
17h 11m
1 stop
MDW10:11 pmChicago Midway
$185
Frontier
Jun 9
MDW6:00 amChicago Midway
18h 27m
1 stop
BOS1:27 amBoston Logan Intl
Jun 10
BOS6:00 amBoston Logan Intl
17h 11m
1 stop
MDW10:11 pmChicago Midway
$186

Southwest flights from Illinois to Boston

Our best Southwest deals on Illinois to Boston flight tickets
Southwest
Jun 9
MDW9:00 amChicago Midway
2h 15m
BOS12:15 pmBoston Logan Intl
Jun 10
BOS5:35 amBoston Logan Intl
2h 35m
MDW7:10 amChicago Midway
$187
Southwest
Jun 9
MDW9:00 amChicago Midway
2h 15m
BOS12:15 pmBoston Logan Intl
Jun 16
BOS5:35 amBoston Logan Intl
2h 35m
MDW7:10 amChicago Midway
$192
Southwest
Jun 10
MDW9:00 amChicago Midway
2h 15m
BOS12:15 pmBoston Logan Intl
Jun 11
BOS5:25 amBoston Logan Intl
2h 35m
MDW7:00 amChicago Midway
$196

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Boston 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 16, 2026.
Use the filters below to find and compare flights from Illinois to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 6/9

6:00 am-1:27 am

1 stop18h 27m

Boston Logan Intl

Wed 6/10

6:00 am-10:11 pm

1 stop17h 11m

$169

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/28

8:30 pm-11:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 5/31

6:00 am-8:00 am

Nonstop3h 00m

$172

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/30

1:56 pm-5:27 pm

Nonstop2h 31m

Boston Logan Intl

Sun 5/31

6:00 am-8:00 am

Nonstop3h 00m

$176

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 6/9

6:00 am-1:27 am

1 stop18h 27m

Boston Logan Intl

Wed 6/10

6:00 am-10:11 pm

1 stop17h 11m

$185

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/9

3:15 pm-6:50 pm

Nonstop2h 35m

Boston Logan Intl

Wed 6/10

7:46 pm-10:00 pm

Nonstop3h 14m

$186

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/30

7:00 am-10:35 am

Nonstop2h 35m

Boston Logan Intl

Sat 5/30

5:30 pm-7:33 pm

Nonstop3h 03m

$187
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 6/9

9:00 am-12:15 pm

Nonstop2h 15m

Boston Logan Intl

Wed 6/10

5:35 am-7:10 am

Nonstop2h 35m

$187

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 6/9

9:00 am-12:15 pm

Nonstop2h 15m

Boston Logan Intl

Tue 6/16

5:35 am-7:10 am

Nonstop2h 35m

$192

ChampaignBoston

CMI - BOS

CMIBOS

Champaign University-Willard

Sat 6/6

6:43 pm-12:28 am

1 stop4h 45m

Boston Logan Intl

Sat 6/13

5:00 am-11:05 am

1 stop7h 05m

$306

MolineBoston

MLI - BOS

MLIBOS

Moline Quad-City

Wed 9/9

5:00 pm-1:06 am

1 stop7h 06m

Boston Logan Intl

Wed 9/23

4:20 pm-10:30 pm

1 stop7h 10m

$325

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 Boston from

How to get the cheapest flight ticket from Illinois to Boston

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 Boston?

In general, November is the cheapest month to fly from Illinois to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $184. If you aren’t able to travel during the month of November, then book flights to Boston from Illinois during September instead. Flights to Boston in September, while not as cheap as those in November, still average around $190.

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

The cheapest day to depart from Illinois to Boston is on a Wednesday when prices can be found for as low as $235. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $302.

What is the cheapest time of day to depart on your flight to Boston?

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Illinois to Boston in the evening for as low as $215. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $289 per ticket.

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

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

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

You are more likely to see cheaper flights to Boston from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $236 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Illinois for as low as $203 on momondo.

Can stopping save me money on Illinois to Boston flights?

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

Cheap Illinois to Boston flight deals and tips

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

Best Price Found

$108

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Illinois in the past 72 hours is $108. The best round-trip flight deal from Illinois to Boston found on momondo in the last 72 hours is $211.
The fastest flight from Illinois to Boston takes 2h 10m
Direct flights go from Illinois to Boston every day.
There is 1 airport in Boston. From Illinois there are direct flights to Boston Logan Intl (BOS).
Search flight deals

Frequently asked questions about flying from Illinois to Boston

  • When did momondo last update prices for flights from Illinois to Boston Logan Intl Airport?

    Prices for flights from Illinois to Boston Logan Intl Airport were last updated today.

  • How many operators does momondo search for flights from Illinois to Boston Logan Intl Airport?

  • How old do you have to be to fly from Illinois to Boston Logan Intl Airport?

    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 Illinois to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Illinois to Boston

Compare and see reviews for airlines that fly from Illinois to Boston with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $68Free CancellationRating
7.1
2,977 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $79Free CancellationRating
6.2
8,625 reviews
Search Spirit Airlines flights
DeltaPriceFrom $87Free CancellationRating
7.9
8,455 reviews
Search Delta flights
United AirlinesPriceFrom $122Free CancellationRating
7.4
9,727 reviews
Search United Airlines flights
SouthwestPriceFrom $126Free CancellationRating
8.0
4,298 reviews
Search Southwest flights
American AirlinesPriceFrom $127Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Salem
Ogunquit
Old Orchard Beach
Hampton
York Beach
Kennebunkport
Cambridge
Plymouth
South Yarmouth
Gloucester
Narragansett
Falmouth
Brockton
Chatham
Warwick
Sturbridge
Laconia
Dennis Port
Nashua

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Boston. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

Once all potential Illinois to Boston 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 Illinois to Boston right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Boston from Illinois. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Boston trip

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