Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Illinois to Boston from $94

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 10/2. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:30 pm - 8:11 pm
ORD
-
BOS
2h 41mnonstop
Delta Logo
8:50 pm - 10:32 pm
BOS
-
ORD
2h 42mnonstop
$173Delta
Sat, Sep 5 - Wed, Sep 9
JetBlue Logo
9:35 am - 5:07 pm
ORD
-
BOS
6h 32m
1 stop
JetBlue Logo
2:45 pm - 9:58 pm
BOS
-
ORD
8h 13m
1 stop
$174JetBlue
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
7:20 pm - 9:00 pm
BOS
-
MDW
2h 40mnonstop
$175Southwest
Fri, Jul 31 - Tue, Aug 4
Southwest Logo
5:45 pm - 9:10 pm
MDW
-
BOS
2h 25mnonstop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$178Southwest
Sat, Jul 25 - Mon, Jul 27
United Airlines Logo
9:40 pm - 1:10 am
ORD
-
BOS
2h 30mnonstop
United Airlines Logo
7:05 am - 9:03 am
BOS
-
ORD
2h 58mnonstop
$178United Airlines
Sat, Sep 5 - Fri, Sep 11
American Airlines Logo
5:30 pm - 11:36 pm
PIA
-
BOS
5h 06m
1 stop
American Airlines Logo
6:00 am - 10:56 am
BOS
-
PIA
5h 56m
1 stop
$319American Airlines
Thu, Oct 29 - Sun, Nov 1
American Airlines Logo
4:57 pm - 11:59 pm
MLI
-
BOS
6h 02m
1 stop
American Airlines Logo
6:00 pm - 12:11 am
BOS
-
MLI
7h 11m
2 stops
$324American Airlines
Sat, Oct 3 - Wed, Oct 7
United Airlines Logo
1:15 pm - 7:19 pm
MLI
-
BOS
5h 04m
1 stop
United Airlines Logo
5:45 am - 12:21 pm
BOS
-
MLI
7h 36m
2 stops
$352United Airlines
Thu, Aug 20 - Sun, Aug 23
Frontier Logo
4:09 pm - 9:09 am
STL
-
BOS
16h 00m
1 stop
Frontier Logo
10:04 am - 11:59 pm
BOS
-
STL
14h 55m
1 stop
$352Frontier
Fri, Jul 24 - Tue, Jul 28
Frontier Logo
4:09 pm - 9:09 am
STL
-
BOS
16h 00m
1 stop
Frontier Logo
8:41 am - 8:57 am
BOS
-
STL
25h 16m
2 stops
$353Frontier
Mon, Jul 20 - Fri, Jul 24

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

Southwest flights from Illinois to Boston

Our best Southwest deals on Illinois to Boston flight tickets
Southwest
Jul 31
MDW7:35 pmChicago Midway
2h 20m
BOS10:55 pmBoston Logan Intl
Aug 4
BOS7:20 pmBoston Logan Intl
2h 40m
MDW9:00 pmChicago Midway
$175
Southwest
Jul 25
MDW5:45 pmChicago Midway
2h 25m
BOS9:10 pmBoston Logan Intl
Jul 27
BOS5:25 amBoston Logan Intl
2h 35m
MDW7:00 amChicago Midway
$178
Southwest
Jul 28
MDW2:40 pmChicago Midway
2h 20m
BOS6:00 pmBoston Logan Intl
Jul 31
BOS5:25 amBoston Logan Intl
2h 35m
MDW7:00 amChicago Midway
$179

JetBlue flights from Illinois to Boston

Our best JetBlue deals on Illinois to Boston flight tickets
JetBlue
Aug 6
ORD9:35 amChicago O'Hare Intl
6h 32m
1 stop
BOS5:07 pmBoston Logan Intl
Aug 11
BOS2:45 pmBoston Logan Intl
8h 13m
1 stop
ORD9:58 pmChicago O'Hare Intl
$174
JetBlue
Sep 5
ORD1:49 pmChicago O'Hare Intl
3h 10m
BOS5:59 pmBoston Logan Intl
Sep 9
BOS6:55 amBoston Logan Intl
5h 52m
1 stop
ORD11:47 amChicago O'Hare Intl
$175
JetBlue
Jul 22
ORD6:00 amChicago O'Hare Intl
7h 22m
1 stop
BOS2:22 pmBoston Logan Intl
Jul 26
BOS5:01 amBoston Logan Intl
4h 49m
1 stop
ORD8:50 amChicago O'Hare Intl
$176

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 July 2, 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

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/5

4:30 pm-8:11 pm

Nonstop2h 41m

Boston Logan Intl

Wed 9/9

8:50 pm-10:32 pm

Nonstop2h 42m

$173

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 8/6

9:35 am-5:07 pm

1 stop6h 32m

Boston Logan Intl

Tue 8/11

2:45 pm-9:58 pm

1 stop8h 13m

$174
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 7/31

7:35 pm-10:55 pm

Nonstop2h 20m

Boston Logan Intl

Tue 8/4

7:20 pm-9:00 pm

Nonstop2h 40m

$175

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 7/25

5:45 pm-9:10 pm

Nonstop2h 25m

Boston Logan Intl

Mon 7/27

5:25 am-7:00 am

Nonstop2h 35m

$178

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/5

9:40 pm-1:10 am

Nonstop2h 30m

Boston Logan Intl

Fri 9/11

7:05 am-9:03 am

Nonstop2h 58m

$178

PeoriaBoston

PIA - BOS

PIABOS

Greater Peoria

Thu 10/29

5:30 pm-11:36 pm

1 stop5h 06m

Boston Logan Intl

Sun 11/1

6:00 am-10:56 am

1 stop5h 56m

$319

MolineBoston

MLI - BOS

MLIBOS

Moline Quad-City

Sat 10/3

4:57 pm-11:59 pm

1 stop6h 02m

Boston Logan Intl

Wed 10/7

6:00 pm-12:11 am

2 stops7h 11m

$324

MolineBoston

MLI - BOS

MLIBOS

Moline Quad-City

Thu 8/20

1:15 pm-7:19 pm

1 stop5h 04m

Boston Logan Intl

Sun 8/23

5:45 am-12:21 pm

2 stops7h 36m

$352

St. LouisBoston

STL - BOS

STLBOS

Lambert-St Louis

Fri 7/24

4:09 pm-9:09 am

1 stop16h 00m

Boston Logan Intl

Tue 7/28

10:04 am-11:59 pm

1 stop14h 55m

$352

St. LouisBoston

STL - BOS

STLBOS

Lambert-St Louis

Mon 7/20

4:09 pm-9:09 am

1 stop16h 00m

Boston Logan Intl

Fri 7/24

8:41 am-8:57 am

2 stops25h 16m

$353

Flights are sorted by cheapest round-trip flights first.

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

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 $183. 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 $191.

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

The cheapest day to depart from Illinois to Boston is on a Saturday when prices can be found for as low as $242. 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 $313.

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 $230. 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 $293 per ticket.

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

Fly from Chicago O'Hare Intl 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 $242 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 $210 on momondo.

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

There are 4 cabin classes available to choose from on Illinois to Boston 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 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

$128

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 $128. The best round-trip flight deal from Illinois to Boston found on momondo in the last 72 hours is $212.
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
3,008 reviews
Search JetBlue flights
DeltaPriceFrom $81Free CancellationRating
7.8
8,452 reviews
Search Delta flights
SouthwestPriceFrom $114Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
9,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.1
11,768 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
Cambridge
York Beach
Plymouth
Kennebunkport
South Yarmouth
Laconia
Revere
Gloucester
Warwick
Brockton
Falmouth
South Portland
Narragansett
Middletown
Chatham

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

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
Sat 8/1
Sat 8/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States